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1. Compound ID: 350
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a-L-Fucp-(1-2)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc |
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Structure type: fragment of a bigger structure
Trivial name: monofucosyl A type 1 histo-blood group epitope
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 99
Therisod H, Monteiro MA, Perry MB, Caroff M "Helicobacter mustelae lipid A structure differs from that of Helicobacter pylori" -
FEBS Letters 499(1-2) (2001) 1-5
The lipid A structure of the Gram-negative bacterium Helicobacter mustelae, a ferret gastric pathogen responsible for the onset of gastric diseases in its host, was investigated. Two variant lipid A structures were found in the same strain. One structure contained a bisphosphorylated β-(1→6)-linked D-glucosamine backbone disaccharide with hydroxytetradecanoic acid in amide linkages. Unlike the structure described for the lipid A of the related human Helicobacter pylori gastric pathogen, which contains a C1 phosphate moiety, this lipid A presented phosphate groups at both the C1 and C4' positions, and contained no octadecanoyl fatty acid, which is present in H. pylori. The second lipid A structure had a different fatty acid composition in that 3-OH C(16) replaced most of the amide-linked 3-OH C(14).
structure, lipid A, endotoxin, Helicobacter mustelae, Helicobacter pylori
NCBI PubMed ID: 11418100Publication DOI: 10.1016/S0014-5793(01)02496-6Journal NLM ID: 0155157Publisher: Elsevier
Correspondence: martine.caroff@bbmpc.u-psud.fr
Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, Biochimie, Université de Paris-Sud, Orsay, France, Institute for Biological Sciences, National Research Council of Canada, Ottawa, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, de-O-acylation, TLC, 31P NMR, GC, MALDI-TOF MS, composition analysis, PD-MS, NMR-1D
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2. Compound ID: 401
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R-Pyr-(2-6:2-4)-+
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b-D-Galf-(1-3)-+ |
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-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: zwitterionic polysaccharide A1, zwitterionic polysaccharide, PS A1, polysaccharide A1
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 134
Tzianabos A, Wang JY, Kasper DL "Biological chemistry of immunomodulation by zwitterionic polysaccharides" -
Carbohydrate Research 338(23) (2003) 2531-2538
Capsular polysaccharides isolated from pathogenic bacteria are comprised typically of many repeating units from one to eight or more monosaccharides in length. These polysaccharides stimulate the murine humoral immune system to elicit primarily IgM antibody responses. Studies conducted primarily in the mouse have characterized these polymers as T cell-independent antigens. These mouse studies and the relatively poor immunogenicity of polysaccharides in human hosts have led to the design of vaccines by coupling these polysaccharides to protein carriers to stimulate a T cell-dependent response. However, a newly described class of bacterial polysaccharides has been characterized that have the ability to modulate the cellular immune system. They are structurally diverse, but all share a zwitterionic charge motif that allows them to directly interact with T cells and antigen-presenting cells to initiate an immunomodulatory T cell response. These polymers, termed zwitterionic polysaccharides (ZPSs), elicit T cell-derived chemokines and cytokines that influence the immune response governing at least one classic host response to bacterial infection: abscess formation. This review will describe the biological and structural aspects of ZPSs that convey these activities.
polysaccharides, T cell, structure/function
NCBI PubMed ID: 14670714Publication DOI: 10.1016/j.carres.2003.06.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: atzianabos@channing.harvard.edu
Institutions: Department of Medicine, Channing Laboratory, 181 Longwood Ave., Brigham and Women's Hospital, Boston, MA 02115, USA
- Article ID: 135
Tzianabos AO "Polysaccharide immunomodulators as therapeutic agents: structural aspects and biologic function" -
Clinical Microbiology Reviews 13(4) (2000) 523-533
Polysaccharide immunomodulators were first discovered over 40 years ago. Although very few have been rigorously studied, recent reports have revealed the mechanism of action and structure-function attributes of some of these molecules. Certain polysaccharide immunomodulators have been identified that have profound effects in the regulation of immune responses during the progression of infectious diseases, and studies have begun to define structural aspects of these molecules that govern their function and interaction with cells of the host immune system. These polymers can influence innate and cell-mediated immunity through interactions with T cells, monocytes, macrophages, and polymorphonuclear lymphocytes. The ability to modulate the immune response in an appropriate way can enhance the host's immune response to certain infections. In addition, this strategy can be utilized to augment current treatment regimens such as antimicrobial therapy that are becoming less efficacious with the advent of antibiotic resistance. This review focuses on recent studies that illustrate the structural and biologic activities of specific polysaccharide immunomodulators and outlines their potential for clinical use.
structural, polysaccharide, polysaccharides, function, agent, cellular, immunity, immunomodulator, review, therapeutic
Publication DOI: 10.1128/CMR.13.4.523-533.2000Journal NLM ID: 8807282Publisher: Washington, DC: American Society for Microbiology
Correspondence: atzianabos@channing.harvard.edu
Institutions: Channing Laboratory, Brigham and Women's Hospital, Harvard Medical School, 181 Longwood Ave., Boston, MA 02115
- Article ID: 1766
Baumann H, Tzianabos AO, Brisson JR, Kasper DL, Jennings HJ "Structural elucidation of two capsular polysaccharide from one strain of Bacteroides fragilis using high-resolution NMR spectroscopy two ionically linked polysaccharides" -
Biochemistry 31 (1992) 4081-4082
The capsule of Bacteroides fragilis is unusual in that it consists of two distinct capsular polysaccharides. Using a combination of high-resolution NMR spectroscopy, theoretical calculations, and as few chemical procedures as required, the structure of both polysaccharide antigens (polysaccharides A and B) was elucidated. Using the above procedures, it was possible to obtain the complete structures using minimal quantities of polysaccharides A and B (8 and 5 mg, respectively). Only small amounts of each subjected to chemical analysis were not recoverable. Polysaccharide A is composed of the following repeating unit: [→3)α-D-AATp(1→4)[β-D-Galf(1→3)]α-D-GalpNAc(1→3)β-D-Galp(1→], where AAT is 2-acetamido-4-amino-2,4,6-trideoxygalactose. A pyruvate substituent having the R configuration spans O-4 and O-6 of the β-D-galactopyranosyl residue. Polysaccharide B is composed of the following repeating unit: [→4)α-L-QuipNAc(1→3)β-D-QuipNAc(1→4)[α-L-Fucp(1→2)β-D-GalpA(1→3)β-D-GlcpNAc(1→3)]α-D-Galp(1→]. A 2-aminoethylphosphonate substituent is situated on O-4 of the N-acetyl-β-D-glucopyranosyl residue
NCBI PubMed ID: 1567854Publication DOI: 10.1021/bi00131a026Journal NLM ID: 0370623Publisher: American Chemical Society
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
Methods: 13C NMR, 1H NMR, 31P NMR
- Article ID: 2551
Tzianabos AO, Onderdonk AB, Smith RS, Kasper DL "Structure-function relationships for polysaccharide-induced intra-abdominal abscesses" -
Infection and Immunity 62 (1994) 3590-3593
Journal NLM ID: 0246127Publisher: American Society for Microbiology
- Article ID: 2660
Tzianabos AO, Pantosti A, Baumann H, Brisson JR, Jennings HJ, Kasper DL "The capsular polysaccharide of Bacteroides fragillis comprises two ionically linked polysaccharides" -
Journal of Biological Chemistry 267 (1992) 18230-18235
Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
- Article ID: 2808
Tzianabos AO, Onderdonk AB, Rosner B, Cisneros RL, Kasper DL "Structural features of polysaccharides that induce intra-abdominal abscesses" -
Science 262 (1993) 416-419
Journal NLM ID: 0404511Publisher: Washington, DC: American Association for the Advancement of Science
- Article ID: 3306
Tzianabos AO, Onderdonk AB, Zaleznik DF, Smith RS, Kasper DL "Structural characteristics of polysaccharides that induce protection against intra-abdominal abscess formation" -
Infection and Immunity 62 (1994) 4881-4886
Bacteroides fragilis is the anaerobe most commonly isolated from clinical cases of intra-abdominal sepsis. In a rodent model of this disease process, intraperitoneal injection of the capsular polysaccharide complex (CPC) from B. fragilis provokes abscess formation, while subcutaneous administration of this complex confers protection against B. fragilis-induced intra-abdominal abscesses. The CPC consists of two discrete polysaccharides, polysaccharides A and B (PS A and PS B), each possessing oppositely charged structural groups critical to the ability of these carbohydrates to induce the formation of abscesses. Other bacterial polysaccharides that possess oppositely charged groups (such as the group antigen or capsular polysaccharide from Streptococcus pneumoniae type 1 strains) also exhibited potent abscess-inducing capabilities. We report here that positively and negatively charged groups on polysaccharides are also essential for inducing protection against abscess formation. Vaccination of rats with B. fragilis PS A, PS B, or the S. pneumoniae type 1 capsule protected against intra-abdominal abscesses subsequent to intraperitoneal challenge with each of these polysaccharides. Chemical conversion of the free amino or carboxyl groups on PS A to uncharged N-acetyl or hydroxymethyl groups, respectively, abrogated the ability of this polymer to confer protection against polysaccharide-mediated abscess formation. Adoptive transfer of splenic T cells from polysaccharide-vaccinated rats to naive animals demonstrated that T cells mediated this protective activity. T cells transferred from animals vaccinated with a polysaccharide repeating unit (Salmonella typhi Vi antigen) that normally contains one carboxyl group but was chemically converted to a polymer that possesses both free amino and carboxyl groups (accomplished by de-N-acetylating the Vi antigen) protected naive T-cell recipients against polysaccharide-induced abscesses. These results demonstrate that a distinct structural motif associated with the B. fragilis polysaccharides is necessary for induction of protective immunity against abscess formation associated with intra-abdominal sepsis. However, protection is not antigen specific in a traditional sense. Rather, the protective ability of these structurally dissimilar polysaccharides is conferred by, and perhaps specific for, a motif of oppositely charged groups.
Streptococcus pneumoniae, capsular polysaccharide, sepsis, Salmonella typhi, Bacteroides, Bacteroides fragilis, Vi-antigen, rats, vaccination
NCBI PubMed ID: 7927768Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Channing Laboratory, Brigham and Women's Hospital, Departments of Medicine, Boston, Massachusetts 02115.
Methods: chemical methods, serological methods, statistical analysis
- Article ID: 5790
Khanam A, Tiwari A, Mandal PK "Chiral auxiliaries: Usefullness in stereoselective glycosylation reactions and their synthetic applications" -
Carbohydrate Research 495 (2020) 108045
Oligosaccharides play a very important role in biological system and structure-activity relationships that is why it has a lot of application to medicinal chemistry and development of polysaccharide conjugate vaccines. The stereoselective introduction of a glycosidic linkage presents the principal challenge for biological importance oligosaccharide synthesis. The main aim of this review is to described the importance of chiral auxiliary and neibhouring group participation for the stereoselective 1,2-cis glycosidic bonds formation and their application in complex oligosaccharide synthesis.Numerous 1,2-cis-linked oligosaccharides and glyconjugates are naturally found in the compounds of blood group, human milk, antigens of bacterial lipopolysaccharide etc.that predominantly increased it's importance in this field.
Oligosaccharides, glycosylation, stereoselective, 1, 2-Cis glycosidic bonds, Chiral auxiliary
NCBI PubMed ID: 32679340Publication DOI: 10.1016/j.carres.2020.108045Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: pk.mandal@cdri.res.in
Institutions: Academy of Scientific and Innovative Research, New Delhi, India, Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow, 226031, India.Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow, 226031, India
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 6123
Pathan EK, Ghosh B, Podilapu AR, Kulkarni SS "Total Synthesis of the Repeating Unit of Bacteroides fragilis Zwitterionic Polysaccharide A1" -
Journal of Organic Chemistry 86(9) (2021) 6090-6099
Zwitterionic polysaccharides isolated from commensal bacteria are endowed with unique immunological properties and are emerging as immunotherapeutic agents as well as vaccine carriers. Reported herein is a total synthesis of the repeating unit of Bacteroides fragilis zwitterionic polysaccharide A1 (PS A1). The structurally complex tetrasaccharide unit contains a rare sugar 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT) and two consecutive 1,2-cis glycosidic linkages. The repeating unit was efficiently assembled by rapid synthesis of d-galactosamine and AAT building blocks from cheap and abundant d-mannose via a one-pot SN2 displacement of 2,4-bistriflates and installation of all of the glycosidic bonds in a highly stereoselective manner. The total synthesis involves a longest linear sequence of 17 steps with 3.47% overall yield.
synthesis, repeating unit, vaccine, Bacteroides fragilis, total synthesis, zwitterionic polysaccharide A1
NCBI PubMed ID: 33843231Publication DOI: 10.1021/acs.joc.0c02935Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: Suvarn S. Kulkarni <: suvarn@chem.iitb.ac.in>
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, HPLC, glycosylation, optical rotation measurement, HR-ESI-MS
- Article ID: 6201
Banahene N, Kavunja HW, Swarts BM "Chemical reporters for bacterial glycans: development and applications" -
Chemical Reviews 122(3) (2022) 3336-3413
Bacteria possess an extraordinary repertoire of cell envelope glycans that have critical physiological functions. Pathogenic bacteria have glycans that are essential for growth and virulence but are absent from humans, making them high-priority targets for antibiotic, vaccine, and diagnostic development. The advent of metabolic labeling with bioorthogonal chemical reporters and small-molecule fluorescent reporters has enabled the investigation and targeting of specific bacterial glycans in their native environments. These tools have opened the door to imaging glycan dynamics, assaying and inhibiting glycan biosynthesis, profiling glycoproteins and glycan-binding proteins, and targeting pathogens with diagnostic and therapeutic payload. These capabilities have been wielded in diverse commensal and pathogenic Gram-positive, Gram-negative, and mycobacterial species-including within live host organisms. Here, we review the development and applications of chemical reporters for bacterial glycans, including peptidoglycan, lipopolysaccharide, glycoproteins, teichoic acids, and capsular polysaccharides, as well as mycobacterial glycans, including trehalose glycolipids and arabinan-containing glycoconjugates. We cover in detail how bacteria-targeting chemical reporters are designed, synthesized, and evaluated, how they operate from a mechanistic standpoint, and how this information informs their judicious and innovative application. We also provide a perspective on the current state and future directions of the field, underscoring the need for interdisciplinary teams to create novel tools and extend existing tools to support fundamental and translational research on bacterial glycans.
biosynthesis, polysaccharides, glycoconjugates, glycan, Gram-negative bacteria, gram-positive bacteria
NCBI PubMed ID: 34905344Publication DOI: 10.1021/acs.chemrev.1c00729Journal NLM ID: 2985134RPublisher: Chem Rev
Correspondence: ben.swarts@cmich.edu
Institutions: Department of Chemistry and Biochemistry, Central Michigan University, Mount Pleasant, Michigan 48859, United States, Biochemistry, Cell, and Molecular Biology Program, Central Michigan University, Mount Pleasant, Michigan 48859, United States
- Article ID: 6299
Qin C, Li L, Tian G, Ding M, Zhu S, Song W, Hu J, Seeberger PH, Yin J "Chemical Synthesis and Antigenicity Evaluation of Shigella dysenteriae Serotype 10 O-Antigen Tetrasaccharide Containing a (S)-4,6-O-Pyruvyl Ketal" -
Journal of the American Chemical Society 144(46) (2022) 21068-21079
Shigella is the second most common etiologic pathogen responsible for childhood acute diarrhea. An anti-Shigella vaccine is still eagerly awaited due to the increasing drug resistance of this pathogen. The Shigella O-antigen is a promising vaccine target. To identify the immune epitopes of the glycan, the first total synthesis of Shigella dysenteriae serotype 10 O-antigen tetrasaccharide containing a (S)-4,6-O-pyruvyl ketal was completed. The 1,2-trans-β-glycosylation & C2 epimerization and conformational locking strategies facilitated the construction of two 1,2-cis-β-glycosidic linkages. The reactivities of both the glycosyl donor and acceptor were improved by adding electron-donating benzyl groups, enabling an efficient assembly of the tetrasaccharide. The (S)-4,6-O-pyruvyl ketal was introduced at the final stage due to its influence on the glycosylation stereospecificity and efficiency. In addition, (R)-4,6-O-pyruvylated and nonpyruvylated tetrasaccharides and three further fragments were synthesized. Glycan microarray screening revealed that the tetrasaccharide repeating unit is the key antigenic epitope of the O-antigen. Moreover, the (S)-4,6-O-pyruvyl ketal is an essential structural feature of this antigen for designing carbohydrate-based vaccines against S. dysenteriae serotype 10. The comparison of the (S)-4,6-O-pyruvylated glycan and its (R)-epimer will set an example for biological evaluation of other bacterial glycans containing pyruvyl ketals.
synthesis, serotype, O-antigen, glycosylation, vaccine
NCBI PubMed ID: 36354960Publication DOI: 10.1021/jacs.2c05953Journal NLM ID: 7503056Publisher: American Chemical Society
Correspondence: Jian Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Lihu Avenue 1800, Wuxi, Jiangsu 214122, P. R. China, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, Potsdam 14476, Germany, Wuxi School of Medicine, Jiangnan University, Lihu Avenue 1800, Wuxi, Jiangsu 214122, P. R. China
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, RP-HPLC, HR-ESI-MS, microarray binding assays
- Article ID: 6301
Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" -
Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.
chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal
NCBI PubMed ID: 35750381Publication DOI: 10.1016/S1875-5364(22)60177-8Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: J. Yin
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
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3. Compound ID: 872
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a-D-Galp-(1-6)-+
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-3)-a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS, CPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140529,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_152213,IEDB_153205,IEDB_167069,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 243
Griffin AM, Morris VJ, Gasso MJ "The cpsABCDE genes involved in polysaccharide production in Streptococcus salivarius ssp thermophilus strain NCBF 2393" -
Gene 183 (1996) 23-27
A 4074-bp EcoRI fragment of Streptococcus salivarius ssp. thermophilus (S. thermophilus) chromosomal DNA containing genes involved in exocellular polysaccharide (EPS) was identified and cloned. The nucleotide sequence of this fragment was determined and found to contain one partial and four complete open reading frames. These were designated cpsA, cpsB, cpsC, cpsD and cpsE and encoded proteins of >130, 243, 230, 246 and 455 amino acids, respectively, that showed homology with the genes of the cps cluster, involved in polysaccharide biosynthesis, in Streptococcus pneumoniae Type 19F. The cpsA gene is predicted to encode a transcriptional regulator, while cpsC anc cpsD are predicted to encode proteins involved in polysaccharide polymerization and export. The cpsE gene is likely to encode the phosphate-prenyl glycosyl-1-phosphate transferase catalyzing the first step in polysaccharide biosynthesis in S. thermophilus. Southern blot analysis revealed that cpsE is found only in polysaccharide producing strains of S. thermophilus.
gene, strain, polysaccharide, Streptococcus, exocellular polysaccharide, production, genetic engineering, lactic acid bacterium, polysaccharide production, ropy strain, Streptococcus salivarius, yoghurt
NCBI PubMed ID: 8996082Journal NLM ID: 7706761Publisher: Amsterdam: Elsevier
Correspondence: annette.griffin@bbsrc.ac.uk
Institutions: Genetic and Mircobiology Department, Institute of Food Research, Norwich Laboratory, Norwich Research Park, Colney, Norwich, NR4 7UA, UK
- Article ID: 1265
Stingele F, Neeser JR, Mollet B "Identification and characterization of the eps (Exopolysaccharide) gene cluster from Streptococcus thermophilus Sfi6" -
Journal of Bacteriology 178(6) (1996) 1680-1690
We report the identification and characterization of the eps gene cluster of Streptococcus thermophilus Sfi6 required for exopolysaccharide (EPS) synthesis. This report is the first genetic work concerning EPS production in a food microorganism. The EPS secreted by this strain consists of the following tetrasaccharide repeating unit: →3)-β-D-Galp-(1→3)-[α-D-Galp-(1→6)]-β-D-D-Galp-(1→3)-α-D-Galp-D-GalpNAc-(1→. The genetic locus The genetic locus was identified by Tn916 mutagenesis in combination with a plate assay to identify Eps mutants. Sequence analysis of the gene region, which was obtained from subclones of a genomic library of Sfi6, revealed a 15.25-kb region encoding 15 open reading frames. EPS expression in the non-EPS-producing heterologous host, Lactococcus lactis MG1363, showed that within the 15.25-kb region, a region with a size of 14.52 kb encoding the 13 genes epsA to epsM was capable of directing EPS synthesis and secretion in this host. Homology searches of the predicted proteins in the Swiss-Prot database revealed high homology (40 to 68+ACU- identity) for epsA, B, C, D, and E and the genes involved in capsule synthesis in Streptococcus pneumoniae and Streptococcus agalactiae. Moderate to low homology (37 to 18+ACU- identity) was detected for epsB, D, F, and H and the genes involved in capsule synthesis in Staphylococcus aureus for epsC, D, and E and the genes involved in exopolysaccharide I (EPSI) synthesis in Rhizobium meliloti for epsC to epsJ and the genes involved in lipopolysaccharide synthesis in members of the Enterobacteriaceae, and finally for eps K and lipB of Neisseria meningitidis. Genes (epsJ, epsL, and epsM) for which the predicted proteins showed little or no homology with proteins in the Swiss-Prot database were shown to be involved in EPS synthesis by single-crossover gene disruption experiments.
gene, characterization, Streptococcus, identification, Streptococcus thermophilus, cluster, gene cluster, exopolysaccharide, EPS
NCBI PubMed ID: 862629Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: francesca.stingele+AEA-chlsnr.nestrd.ch
Institutions: Nestle Research Center, Nestec Ltd., Vers-chez-les-Blanc, 1000 Lausanne 26, Switzerland
- Article ID: 2159
Doco T, Wieruszeski JM, Fournet B, Carcano D, Ramos P, Loones A "Structure of an exocellular polysaccharide produced by Streptococcus thermophilus" -
Carbohydrate Research 198 (1990) 313-321
Streptococcus thermophilus strains grown on skimmed milk produced a viscosifying, exocellular, and water-soluble polysaccharide which contains D-glucose, D-galactose, and N-acetyl-D-galactosamine in the ratio of 1:2:1. Methylation analysis identified the glycosidic linkages in the tetrasaccharidic repeating-unit, and Smith degradation and nitrous deamination after N-deacetylation gave the sequence of monosaccharides in the repeating-unit. The anomeric configurations of the sugar residues were determined by oxidation of the peracetylated polysaccharide with chromium trioxide and by 1H- and 13C-n.m.r. spectroscopy. The following structure was assigned to the repeating unit of the polysaccharide, →3)-β-D-Galp-(1→3)-[α-D-Galp-(1→6)]-β-D-Glcp-(1→3)-α-D-GalpNAc-(1→.
NCBI PubMed ID: 2165858Publication DOI: 10.1016/0008-6215(90)84301-aJournal NLM ID: 0043535Publisher: Elsevier
Institutions: Laboratoire de Chimie Biologique de l'Université des Sciences et Techniques de Lille Flandres-Artois, Unité Associée au C.N.R.S. No 217, Villeneuve d'Ascq, France
Methods: 13C NMR, 1H NMR
- Article ID: 3405
Gorska S, Grycko P, Rybka J, Gamian A "Exopolysaccharides of lactic acid bacteria: structure and biosynthesis" -
Postȩpy Higieny i Medycyny Doświadczalnej [Polish] 61 (2007) 805-818
The group of lactic acid bacteria (LABs) includes four genera: Lactobacillus, Leuconostoc, Pediococcus, and Streptococcus. The most characteristic feature of this group of microorganisms is the production of lactic acid as a main product of carbohydrate metabolism. LABs are responsible for the fermentation of alimentary products and they also produce a variety of agents, among them exopolysaccharides (EPSs), which inhibit the growth of pathogenic bacteria. In this article on the different types of EPSs produced by LABs, data concerning their structure and biosynthesis are presented
biosynthesis, structure, Streptococcus, Lactic acid bacteria, exopolysaccharides, Lactococcus, Lactobacillus, Leuconostoc
NCBI PubMed ID: 18097339Journal NLM ID: 0421052Publisher: Warszawa: Panstwowy Zaklad Wydawnictw Lekarskich
Institutions: Laboratorium Mikrobiologii Lekarskiej, Instytut Immunologii i Terapii Doswiadczalnej PAN im. L. Hirszfelda we Wroclawiu
- Article ID: 5067
Birch J, Harðarson HK, Khan S, Van Calsteren MR, Ipsen R, Garrigues C, Almdal K, Hachem MA, Svensson B "Effect of repeat unit structure and molecular mass of lactic acid bacteria hetero-exopolysaccharides on binding to milk proteins" -
Carbohydrate Polymers 177 (2017) 406-414
Interactions of exopolysaccharides and proteins are of great importance in food science, but complicated to analyze and quantify at the molecular level. A surface plasmon resonance procedure was established to characterize binding of seven structure-determined, branched hetero-exopolysaccharides (HePSs) of 0.14-4.9MDa from lactic acid bacteria to different milk proteins (β-casein, κ-casein, native and heat-treated β-lactoglobulin) at pH 4.0-5.0. Maximum binding capacity (RUmax) and apparent affinity (KA,app) were HePS- and protein-dependent and varied for example 10- and 600-fold, respectively, in the complexation with native β-lactoglobulin at pH 4.0. Highest RUmax and KA,app were obtained with heat-treated β-lactoglobulin and β-casein, respectively. Overall, RUmax and KA,app decreased 6- and 20-fold, respectively, with increasing pH from 4.0 to 5.0. KA,app was influenced by ionic strength and temperature, indicating that polar interactions stabilize HePS-protein complexes. HePS size as well as oligosaccharide repeat structure, conferring chain flexibility and hydrogen bonding potential, influence the KA,app.
Binding parameters, Dynamic light scattering (DLS), Hetero-exopolysaccharides (HePSs), Surface plasmon resonance (SPR), β- and κ-casein, β-lactoglobulin
NCBI PubMed ID: 28962786Publication DOI: 10.1016/j.carbpol.2017.08.055Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: B. Svensson
Institutions: Enzyme and Protein Chemistry, Department of Biotechnology and Biomedicine, Technical University of Denmark, Elektrovej, building 375, DK-2800 Kgs. Lyngby, Denmark, Department of Micro- and Nanotechnology, Technical University of Denmark, Produktionstorvet, building 423, DK-2800 Kgs. Lyngby, Denmark, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, 3600 Casavant Boulevard West, Saint-Hyacinthe, Quebec J2S 8E3, Canada, Department of Food Science, University of Copenhagen, Rolighedsvej 26, DK-1958 Frederiksberg C, Denmark, CED-Discovery, Chr Hansen A/S, DK-2970 Hørsholm, Denmark
Methods: gel filtration, 13C NMR, 1H NMR, sugar analysis, ESI-MS, acid hydrolysis, GC, MS/MS, methanolysis, reduction with NaBD4, acetylation, SPR, protein immobilization, dynamic light scattering
- Article ID: 5075
Pachekrepapol U, Lucey JA, Gong Y, Naran R, Azadi P "Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains" -
Journal of Dairy Science 100(5) (2017) 3424-3435
Exopolysaccharides (EPS) produced by some lactic acid bacteria are often used by the dairy industry to improve the rheological and physical properties of yogurt, but the relationship between their structure and functional effect is still unclear. The EPS from different species, or different strains from the same species, may differ in terms of molar mass, repeating unit structure, and EPS yield during fermentation of milk. This study aimed to characterize the detailed properties of EPS produced from 7 strains of Streptococcus thermophilus, which is one of the key cultures used for yogurt manufacture. Milk was fermented with strains DGCC 7698, DGCC 7710, DGCC 7785, ST-10255y, St-143, STCth-9204, and ST4239. These strains were selected because they have been used in previous studies on yogurt texture, but a complete description of their EPS structural properties has not yet been reported. All strains were fermented under a similar acidification rate by adjusting the level of supplementation with peptone or the inoculation level, which allowed for a comparison of EPS yields under similar growth conditions (reconstituted skim milk at 40°C). The EPS from each strain was isolated and the weight-average molar mass and z-average root mean square radius determined using size-exclusion chromatography multiangle laser light scattering. The monosaccharide composition of EPS was determined using gas chromatography-mass spectrometry, and repeating unit structure was determined using nuclear magnetic resonance spectroscopy. The weight-average molar mass values of EPS ranged from 0.14 to 1.61 × 106 g/mol. All 7 EPS samples were uncharged. The strains ST-10255y and ST4239 had EPS with the same repeating unit structure. The monosaccharide compositions of the various EPS were mainly composed of glucose and galactose, with low levels of rhamnose in the EPS isolated from DGCC 7698, and N-acetylgalactosamine in the EPS from DGCC 7785, ST-10255y, and ST4239. The yields of EPS (measured when fermented milks reached pH 4.6) ranged from 8.0 to 76.4 mg of glucose equivalents/kg. In addition to (free) EPS, some strains were also able to produce capsular polysaccharide (associated with the bacterial cells) when observed with negative staining technique. The results of our study will help the dairy industry to better understand the mechanism by which different strains of Streptococcus thermophilus affect yogurt texture.
Streptococcus thermophilus, exopolysaccharide, acid milk gel, molar mass
NCBI PubMed ID: 28318581Publication DOI: 10.3168/jds.2016-12125Journal NLM ID: 2985126RPublisher: Champaign, IL: American Dairy Science Association
Correspondence: jlucey@cdr.wisc.edu
Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, USA, Department of Food Science, University of Wisconsin-Madison, Madison, USA, Wisconsin Center for Dairy Research, University of Wisconsin-Madison, Madison, USA
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, acid hydrolysis, methanolysis, reduction, dialysis, SEC-MALLS
- Article ID: 5196
Pachekrepapol U, Lucey JA, Gong Y, Naran R, Azadi P "Corrigendum to 'Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains' (J. Dairy Sci. 100:3424-3435)" -
Journal of Dairy Science 101(6) (2018) 5686
U. Pachekrepapol, J.A. Lucey, Y. Gong, R. Naran, P. Azadi Characterization of the chemical structures and physical properties of exopolysaccharides produced by various Streptococcus thermophilus strains J. Dairy Sci., 100 (5) (2017), pp. 3424-3435 DOI:10.3168/jds.2016-12125In Figure 2, on page 3431, the structures of some of the exopolysaccharide repeating units were incorrect. The corrected figure is shown below with revised structures for ST-10255y and ST4239, St-143, and STCth-9204 (Figure 2, parts d, e, and f).
structure, Streptococcus, Streptococcus thermophilus, exopolysaccharide
Publication DOI: 10.3168/jds.2018-101-6-5668Journal NLM ID: 2985126RPublisher: Champaign, IL: American Dairy Science Association
Correspondence: jlucey@cdr.wisc.edu
Institutions: Department of Food Science, University of Wisconsin-Madison, Madison, USA, Wisconsin Center for Dairy Research, University of Wisconsin-Madison, Madison, USA, Complex Carbohydrate Research Center, University of Georgia, Athens 30602
- Article ID: 5533
Zhou Y, Cui Y, Qu X "Exopolysaccharides of lactic acid bacteria: Structure, bioactivity and associations: A review" -
Carbohydrate Polymers 207 (2019) 317-332
The ability to exhibit various bioactivities is widespread in exopolysaccharide (EPS) of lactic acid bacteria (LAB), and it has been admittedly associated with large structural variability of these polymers. Exceptional bioactivities such as cholesterol-lowering, immunomodulating, antioxidant, antiviral and anticoagulant effects render these biopolymers vast commercial value for global market and application potentials in medicine sector. Therefore, an elaborate understanding of structure-to-function associations will be prerequisite to search natural and artificial EPSs for new applications in functional food, health and medicine fields. In this review, it is presented a significant overview of the latest advances in the field of EPS from genes to application. This review emphasized in the general biosynthesis pathway together with genetic modules, multiple structures, functions, and respective functional mechanisms of LAB-derived EPSs, and the relationships between their structure and bioactivity, which will help to exploit new bioactive drugs from LAB-derived EPS.
biosynthesis, structure, exopolysaccharide, mechanism, bioactivity, Structure-to-function association
NCBI PubMed ID: 30600013Publication DOI: 10.1016/j.carbpol.2018.11.093Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Y. Cui
Institutions: Department of Food Science and Engineering, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, China, Institute of Microbiology, Heilongjiang Academy of Sciences, Harbin, China
- Article ID: 5791
Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.
polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component
Publication DOI: 10.1016/B978-0-12-819475-1.00005-5Publisher: Elsevier
Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
Editors: Barchi J, Kamerling H
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
- Article ID: 5880
De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
carbohydrates, polysaccharides, Lactic acid bacteria, exopolysaccharides, glycolipids, glycoproteins, Glycomics
Publication DOI: 10.1016/B978-044451967-2/00129-XPublisher: Elsevier
Correspondence: ldvuyst@vub.ac.be
Editors: Barchi J, Kamerling H
Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
- Article ID: 6033
Birch J, Khan S, Madsen M, Kjeldsen C, Møller MS, Stender EGP, Peters GHJ, Duus J, Kragelund BB, Svensson B "Binding Sites for Oligosaccharide Repeats from Lactic Acid Bacteria Exopolysaccharides on Bovine beta-Lactoglobulin Identified by NMR Spectroscopy" -
ACS Omega 6(13) (2021) 9039-9052
Lactic acid bacterial exopolysaccharides (EPS) are used in the food industry to improve the stability and rheological properties of fermented dairy products. beta-Lactoglobulin (BLG), the dominant whey protein in bovine milk, is well known to bind small molecules such as fatty acids, vitamins, and flavors, and to interact with neutral and anionic polysaccharides used in food and pharmaceuticals. While sparse data are available on the affinity of EPS-milk protein interactions, structural information on BLG-EPS complexes, including the EPS binding sites, is completely lacking. Here, binding sites on BLG variant A (BLGA), for oligosaccharides prepared by mild acid hydrolysis of two EPS produced by Streptococcus thermophilus LY03 and Lactobacillus delbrueckii ssp. bulgaricus CNRZ 1187, respectively, are identified by NMR spectroscopy and supplemented by isothermal titration calorimetry (ITC) and molecular docking of complexes. Evidence of two binding sites (site 1 and site 2) on the surface of BLGA is achieved for both oligosaccharides (LY03-OS and 1187-OS) through NMR chemical shift perturbations, revealing multivalency of BLGA for EPS. The affinities of LY03-OS and 1187-OS for BLGA gave K D values in the mM range obtained by both NMR (pH 2.65) and ITC (pH 4.0). Molecular docking suggested that the BLGA and EPS complexes depend on hydrogen bonds and hydrophobic interactions. The findings provide insights into how BLGA engages structurally different EPS-derived oligosaccharides, which may facilitate the design of BLG-EPS complexation, of relevance for formulation of dairy products and improve understanding of BLGA coacervation.
NMR, Lactic acid bacteria, exopolysaccharide, binding site
NCBI PubMed ID: 33842774Publication DOI: 10.1021/acsomega.1c00060Journal NLM ID: 101691658Publisher: Washington, DC: American Chemical Society
Correspondence: Birthe B. Kragelund
; Birte Svensson
Institutions: Enzyme and Protein Chemistry, Department of Biotechnology and Biomedicine, Technical University of Denmark, Søltofts Plads, Building 224, DK-2800 Kgs. Lyngby, Denmark, NMR Spectroscopy, Department of Chemistry, Technical University of Denmark, Kemitorvet 207, DK-2800 Kgs. Lyngby, Denmark, Biophysical and Biomedicinal Chemistry, Department of Chemistry, Technical University of Denmark, Kemitorvet 206, DK-2800 Kgs. Lyngby, Denmark, Structural Biology and NMR Laboratory, Department of Biology, University of Copenhagen, Ole Maaloes Vej 5, DK-2200 Copenhagen N, Denmark
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, mild acid hydrolysis, MALDI-TOF MS, radiolabeling, HPLC, 15N NMR, cloning, ITC, mutagenesis, molecular docking
- Article ID: 6166
Xu Z, Guo O, Zhang H, Xiong Z, Zhang X, Ai L "Structural characterisation of EPS of Streptococcus thermophilus S-3 and its application in milk fermentation" -
International Journal of Biological Macromolecules 178 (2021) 263-269
The application of Streptococcus thermophilus S-3 into yogurt production was studied and the structural properties of the generated exopolysaccharides (EPS-S3) were characterized. The proposed structure of EPS-S3 was obtained. EPS-S3 contained a high ratio of N-Acetyl-galactosamine with the Mw of 574 kDa, which was higher than that of AR333 (314 kD) leading to higher apparent viscosity. Streptococcus thermophilus strain S-3 was co-cultured with Lactobacillus delbrueckii for yogut production which highly increased the acidifying rate and post-acidification rate. The quality of the co-cultured yogurts in terms of apparent viscosity, syneresis capacity, water holding capacity and rheological properties were much better than that by using Lactobacillus bulgaricus only. The production mechanism of EPS-S3 from gene regulated level was also discussed which is helpful to facilitate the application of Streptococcus thermophilus strain into milk production.
NMR, Streptococcus thermophilus, exopolysaccharides, co-culture
NCBI PubMed ID: 33639187Publication DOI: 10.1016/j.ijbiomac.2021.02.173Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: ailianzhong@163.com
Institutions: Shanghai Engineering Research Center of Food Microbiology, School of Medical Instruments and Food Engineering, University of Shanghai for Science and Technology, Shanghai 200093, China, State Key Laboratory of Dairy Biotechnology, Technology Center Bright Dairy & Food Co., Ltd, Shanghai 200436, China, State Key Laboratory of Food Nutrition and Safety, College of Food Science and Technology, Tianjin University of Science and Technology, Tianjin, China
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, acid hydrolysis, HPLC, function analysis of gene clusters, yogurt production, yogurt quality evaluation
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4. Compound ID: 939
|
b-D-Galf-(1-3)-+ Pyr-(2-6:2-4)-+
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-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 280
Kalka-Moll WM, Tzianabos AO, Wang Y, Carey VJ, Finberg RW, Onderdonk AB, Kasper DL "Effect of molecular size on the ability of zwitterionic polysaccharides to stimulate cellular immunity" -
Journal of Immunology 164(2) (2000) 719-724
The large-molecular-sized zwitterionic capsular polysaccharide of the anaerobe Bacteroides fragilis NCTC 9343, designated polysaccharide (PS) A, stimulates T cell proliferation in vitro and induces T cell-dependent protection against abscess formation in vivo. In the present study, we utilized a modification of a recently developed ozonolytic method for depolymerizing polysaccharides to examine the influence of the molecular size of PS A on cell-mediated immunity. Ozonolysis successfully depolymerized PS A into structurally intact fragments. PS A with average molecular sizes of 129.0 (native), 77.8, 46.9, and 17.1 kDa stimulated CD4+-cell proliferation in vitro to the same degree, whereas the 5.0-kDa fragment was much less stimulatory than the control 129.0-kDa PS A. Rats treated with 129.0-kDa, 46.9-kDa, and 17.1-kDa PS A molecules, but not those treated with the 5.0-kDa molecule, were protected against intraabdominal abscesses induced by challenge with viable B. fragilis. These results demonstrate that a zwitterionic polysaccharide as small as 22 repeating units (88 monosaccharides) elicits a T cell-dependent immune response. These findings clearly distinguish zwitterionic T cell-dependent polysaccharides from T cell-independent polysaccharides and give evidence of the existence of a novel mechanism for a polysaccharide-induced immune response.
polysaccharide, polysaccharides, molecular, cellular, immunity, effect, ability, size
NCBI PubMed ID: 10623815Journal NLM ID: 2985117RPublisher: Bethesda, MD: American Association of Immunologists
Correspondence: dkasper@chainning.harvard.edu
Institutions: Department of Medicine, Channing Laboratory, Brigham and Women's Hospital, Division of Infectious Disease, Dana-Farber Cancer Institute, Harvard Medical School, Boston, MA 02115, USA.
Methods: 1H NMR, ozonolysis
- Article ID: 3386
Kreisman LS, Friedman JH, Neaga A, Cobb BA "Structure-Function Relationships with a T cell Activating Polysaccharide Antigen using Circular Dichroism" -
Glycobiology 17(1) (2007) 46-55
Studies centered on understanding how molecular structure effects biological function have historically focused on proteins. Circular dichroism (CD) is commonly used to analyze protein secondary structure, yet its application to other molecules is far less explored. In fact, little is known about how glycan conformation might effect function, likely due to a lack of tools for measuring dynamic structural changes of carbohydrates. In the present study, we developed a method based on CD to monitor conformational changes in the zwitterionic T cell-activating glycoantigen PSA. We found that PSA helical structure produces a CD spectrum that is strikingly similar to proteins rich in alpha-helical content and is equally sensitive to non-polar solvents. Like conventional T cell-dependent proteins, PSA requires processing before class II major histocompatibility complex (MHCII) binding. CD spectra of PSA fragments of varying sizes indicated that fragments smaller than three repeating units lack helical content and is incapable of MHCII binding. Likewise, neutralization of charged groups in the repeating unit resulted in major conformational changes as measured by CD, which correlated to a lack of MHCII presentation. These data represent two significant findings: CD can be used to measure conformational changes in carbohydrates, and the functional epitope from PSA is dependent upon a specific conformation that is stabilized by adjacent repeating units and a zwitterionic charge motif. As a result, this work demonstrates that CD is a valuable tool for use in functional glycomics efforts that seek to align chemical and conformational structure with biological activity
conformation, polysaccharide, circular dichroism, glycoantigen, MHC class II
NCBI PubMed ID: 16990347Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: brian.cobb@case.edu
Institutions: Department of Pathology, Case Medical School, Cleveland, OH
Methods: serological methods, CD
- Article ID: 4581
Mostafavi AZ, Troutman JM "Biosynthetic assembly of the Bacteroides fragilis capsular polysaccharide A precursor bactoprenyl diphosphate-linked acetamido-4-amino-6-deoxygalactopyranose" -
Biochemistry 52(11) (2013) 1939-1949
The sugar capsule capsular polysaccharide A (CPSA), which coats the surface of the mammalian symbiont Bacteroides fragilis, is a key mediator of mammalian immune system development. In addition, this sugar polymer has shown therapeutic potential in animal models of multiple sclerosis and other autoimmune disorders. The structure of the CPSA polymer includes a rare stereoconfiguration sugar acetamido-4-amino-6-deoxygalactopyranose (AADGal) that we propose is the first sugar linked to a bactoprenyl diphosphate scaffold in the production of CPSA. In this report, we have utilized a heterologous system to reconstitute bactoprenyl diphosphate-linked AADGal production. Construction of this system included a previously reported Campylobacter jejuni dehydratase, PglF, coupled to a B. fragilis-encoded aminotransferase (WcfR) and initiating hexose-1-phosphate transferase (WcfS). The function of the aminotransferase was confirmed by capillary electrophoresis and a novel high-performance liquid chromatography (HPLC) method. Production of the rare uridine diphosphate (UDP)-AADGal was confirmed through a series of one- and two-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry. A spectroscopically unique analogue of bactoprenyl phosphate was utilized to characterize the transfer reaction catalyzed by WcfS and allowed HPLC-based isolation of the isoprenoid-linked sugar product. Importantly, the entire heterologous system was utilized in a single-pot reaction to biosynthesize the bactoprenyl-linked sugar. This work provides the first critical step in the in vitro reconstitution of CPSA biosynthesis.
Bacteroides fragilis, aminotransferase, caspsular polysaccharide A, biosynthesis pathway, WcfR, WcfS, acetamido-4-amino-6-deoxy-galactopyranose
NCBI PubMed ID: 23458065Publication DOI: 10.1021/bi400126wJournal NLM ID: 0370623Publisher: American Chemical Society
Correspondence: jerry.troutman@uncc.edu
Institutions: Department of Chemistry, University of North Carolina at Charlotte , 9201 University City Boulevard, Charlotte, North Carolina 28223-0001, United States
Methods: 1H NMR, NMR-2D, PCR, SDS-PAGE, TLC, ESI-MS, NMR-1D, genetic methods, biochemical methods, radioactivity measurement, HPLC, CE
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5. Compound ID: 1272
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b-D-Galf-(1-3)-+ Pyr-(2-6:2-4)-+
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-3)-a-D-FucpNAc4N-(1-4)-a-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
; n=200
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 399
Tzianabos AO, Finbergi RW, Wang Y, Chani M, Onderdonk AB, Jennings H, Kasper DL "T cells activated by zwitterionic molecules prevent abscesses induced by pathogenic bacteria" -
Journal of Biological Chemistry 275(10) (2000) 6733-6740
Immunologic paradigms classify bacterial polysaccharides as T cell-independent antigens. However, these models fail to explain how zwitterionic polysaccharides (Zps) confer protection against intraabdominal abscess formation in a T cell-dependent manner. Here, we demonstrate that Zps elicit a potent CD41 T cell response in vitro that requires available major histocompatibility complex class II molecules on antigen-presenting cells. Specific chemical modifications to Zps show that: 1) the activity is specific for carbohydrate structure, and 2) the proliferative response depends upon free amino and carboxyl groups on the repeating units of these polysaccharides. Peptides synthesized to mimic the zwitterionic charge motif associated with Zps also exhibited these biologic properties. Lysine-aspartic acid (KD) peptides with more than 15 repeating units stimulated CD41 T cells in vitro and conferred protection against abscesses induced by bacteria such as Bacteroides fragilis and Staphylococcus aureus. Evidence for the biologic importance of T cell activation by these zwitterionic polymers was provided when human CD41 T cells stimulated with these molecules in vitro and adoptively transferred to rats in vivo conferred protection against intraabdominal abscesses induced by viable bacterial challenge. These studies demonstrate that bacterial polysaccharides with a distinct charge motif activate T cells and that this activity confers immunity to a distinctpathologic response to bacterial infection.
bacteria, biological, biochemistry, abscess, cells, activated, pathogenic bacteria, T cells
NCBI PubMed ID: 10702228Publication DOI: 10.1074/jbc.275.10.6733Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: atzianabos@channing.harvard.edu
Institutions: From the Channing Laboratory, Brigham and Women's Hospital, Departments of Medicine, Pathology, and Microbiology and Molecular Genetics, Division of Infectious Disease, Dana Farber Cancer Institute, Harvard Medical School Boston, Massachusetts 02115, the Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, K1A 0R6 Canada
Methods: NMR, serological methods
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6. Compound ID: 1331
|
a-D-GlcpA-(1-4)-+
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-3)-b-D-Galp-(1-6)-a-D-Manp-(1-2)-a-D-Manp-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Aglycon: core
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_130701,IEDB_136044,IEDB_136104,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140630,IEDB_141584,IEDB_141794,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 415
Wang L, Qu WJ, Reeves PR "Sequence analysis of four Shigella boydii O-antigen loci: Implication for Escherichia coli and Shigella relationships" -
Infection and Immunity 69(11) (2001) 6923-6930
Shigella strains are in reality clones of Escherichia coli and are believed to have emerged relatively recently (G. M. Pupo, R. Lan, and P. R. Reeves, Proc. Natl. Acad. Sci. USA 97:10567-10572, 2000). There are 33 O-antigen forms in these Shigella clones, of which 12 are identical to O antigens of other E. coli strains. We sequenced O-antigen gene clusters from Shigella boydii serotypes 4, 5, 6, and 9 and also studied the O53- and O79-antigen gene clusters of E. coli, encoding O antigens identical to those of S. boydii serotype 4 and S. boydii serotype 5, respectively. In both cases the S. boydii and E. coli O-antigen gene clusters have the same genes and organization. The clusters of both S. boydii 6 and S. boydii 9 O antigens have atypical features, with a functional insertion sequence and a wzx gene located in the orientation opposite to that of all other genes in S. boydii serotype 9 and an rmlC gene located away from other rml genes in S. boydii serotype 6. Sequences of O-antigen gene clusters from another three Shigella clones have been published, and two of them also have abnormal structures, with either the entire cluster or one gene being located on a plasmid in Shigella sonnei or Shigella dysenteriae, respectively. It appears that a high proportion of clusters coding for O antigens specific to Shigella clones have atypical features, perhaps indicating recent formation of these gene clusters.
Sequence Analysis, O-antigen, Escherichia, Escherichia coli, Shigella, implication, Shigella boydii
NCBI PubMed ID: 11598067Journal NLM ID: 0246127Publisher: American Society for Microbiology
Correspondence: reeves@angis.org.au
Institutions: Department of Microbiology, The University of Sydney, Sydney, New South Wales 2006, Australia
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7. Compound ID: 1362
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a-D-GlcpNAc-(1-2)-L-gro-a-D-manHepp-(1-3)-+ a-Kdop-(2-4)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
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Structure type: oligomer
Aglycon: lipid A
Trivial name: lipooligosaccharide core L3
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130648,IEDB_130650,IEDB_130659,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_137776,IEDB_1391961,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140089,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149144,IEDB_149569,IEDB_151531,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_2189047,IEDB_226300,IEDB_418762,IEDB_418764,IEDB_418767,IEDB_418769,IEDB_419429,IEDB_885822,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 432
Zhu P, Klutch MJ, Bash MC, Tsang RS, Ng LK, Tsai CM "Genetic diversity of three lgt loci for biosynthesis of lipooligosaccharide (LOS) in Neisseria species" -
Microbiology 148(6) (2002) 1833-1844
Lipooligosaccharide (LOS) is a major virulence factor of the pathogenic NEISSERIA: Nine lgt genes at three chromosomal loci (lgt-1, 2, 3) encoding the glycosyltransferases responsible for the biosynthesis of LOS oligosaccharide chains were examined in 26 Neisseria meningitidis, 51 Neisseria gonorrhoeae and 18 commensal Neisseria strains. DNA hybridization, PCR and nucleotide sequence data were compared to previously reported lgt genes. Analysis of the genetic organization of the lgt loci revealed that in N. meningitidis, the lgt-1 and lgt-3 loci were hypervariable genomic regions, whereas the lgt-2 locus was conserved. In N. gonorrhoeae, no variability in the composition or organization of the three lgt loci was observed. lgt genes were detected only in some commensal Neisseria species. The genetic organization of the lgt-1 locus was classified into eight types and the lgt-3 locus was classified into four types. Two types of arrangement at lgt-1 (II and IV) and one type of arrangement at lgt-3 (IV) were novel genetic organizations reported in this study. Based on the three lgt loci, 10 LOS genotypes of N. meningitidis were distinguished. Phylogenetic analysis revealed a gene cluster, lgtH, which separated from the homologous genes lgtB and lgtE. The lgtH and lgtE genes were mutually exclusive and were located at the same position in lgt-1. The data demonstrated that pathogenic and commensal Neisseria share a common lgt gene pool and horizontal gene transfer appears to contribute to the genetic diversity of the lgt loci in Neisseria
biosynthesis, oligosaccharide structure, Neisseria meningitidis, Neisseria, gene cluster, glycosyltransferases, Gonorrhoeae, Neisseria gonorrhoeae, genetic diversity, lipooligosaccharide (LOS), phylogenetic analysis, virulence factor
NCBI PubMed ID: 12055303Journal NLM ID: 0376646Publisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: zhu@cber.fda.gov
Institutions: Division of Bacterial, Parasitic and Allergenic Products and Division of Viral Products, Center for Biologics Evaluation and Research, FDA, 8800 Rockville Pike, Bethesda, MD, USA
Methods: PCR, DNA sequencing, DNA techniques, genetic methods, RT-PCR
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8. Compound ID: 2489
|
a-Colp-(1-4)-+
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a-Colp-(1-2)-+ |
| |
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-GalpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149568,IEDB_150899,IEDB_151531,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_225177,IEDB_885822,IEDB_885823,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 851
Knirel YA, Senchenkova SN, Jansson P, Weintraub A, Ansaruzzaman M, Albert MJ "Structure of the O-specific polysaccharide of an Aeromonas trota strain cross-reactive with Vibrio cholerae O139 Bengal" -
European Journal of Biochemistry 238 (1996) 160-165
The O-specific polysaccharide of an Aeromonas trota strain was isolated by hydrolysis of the lipopolysaccharide at pH 4.5 followed by gel-permeation chromatography and found to consist of hexasaccharide repeating units containing D-galactose, L-rhamnose, 3,6-dideoxy-L-xylo-hexose (colitose, Col), 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose in the ratios 1:1:2:1:1. Partial hydrolysis of the polysaccharide with 48% hydrofluoric acid resulted in selective removal of colitose to give a modified polysaccharide containing the other four sugar constituents. On the basis of methylation analysis and NMR spectroscopic studies of the initial and modified, colitose-free polysaccharide, it was concluded that the repeating unit of the O-specific polysaccharide has the following structure [sequence: see text] The known cross-reactivity between the strain studied and Vibrio cholerae O139 Bengal is substantiated by the presence of a common colitose-containing epitope shared by the O-specific polysaccharide of A. trota and the capsular polysaccharide of V. cholerae, which is thought to carry determinants of O-specificity.
Lipopolysaccharide, LPS, structure, strain, polysaccharide, O-specific, O-specific polysaccharide, methylation, Vibrio, Vibrio cholerae, Vibrio cholerae O139, cross-reactive, Aeromonas, Aeromonas trota
NCBI PubMed ID: 8665933Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pjansson@kfc.ki.se
Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
Methods: methylation, partial acid hydrolysis, NMR, HF solvolysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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9. Compound ID: 2490
|
-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-4)-a-L-Rhap-(1-3)-a-D-GalpNAc-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, CPS
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_143794,IEDB_149568,IEDB_150899,IEDB_151531,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_225177,IEDB_885822,IEDB_885823,SB_137,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 851
Knirel YA, Senchenkova SN, Jansson P, Weintraub A, Ansaruzzaman M, Albert MJ "Structure of the O-specific polysaccharide of an Aeromonas trota strain cross-reactive with Vibrio cholerae O139 Bengal" -
European Journal of Biochemistry 238 (1996) 160-165
The O-specific polysaccharide of an Aeromonas trota strain was isolated by hydrolysis of the lipopolysaccharide at pH 4.5 followed by gel-permeation chromatography and found to consist of hexasaccharide repeating units containing D-galactose, L-rhamnose, 3,6-dideoxy-L-xylo-hexose (colitose, Col), 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose in the ratios 1:1:2:1:1. Partial hydrolysis of the polysaccharide with 48% hydrofluoric acid resulted in selective removal of colitose to give a modified polysaccharide containing the other four sugar constituents. On the basis of methylation analysis and NMR spectroscopic studies of the initial and modified, colitose-free polysaccharide, it was concluded that the repeating unit of the O-specific polysaccharide has the following structure [sequence: see text] The known cross-reactivity between the strain studied and Vibrio cholerae O139 Bengal is substantiated by the presence of a common colitose-containing epitope shared by the O-specific polysaccharide of A. trota and the capsular polysaccharide of V. cholerae, which is thought to carry determinants of O-specificity.
Lipopolysaccharide, LPS, structure, strain, polysaccharide, O-specific, O-specific polysaccharide, methylation, Vibrio, Vibrio cholerae, Vibrio cholerae O139, cross-reactive, Aeromonas, Aeromonas trota
NCBI PubMed ID: 8665933Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pjansson@kfc.ki.se
Institutions: Karolinska Institute, Clinical Research Center, Huddinge University Hospital, Huddinge, Sweden
Methods: methylation, partial acid hydrolysis, NMR, HF solvolysis
- Article ID: 4358
Nazarenko EL, Crawford RJ, Ivanova EP "The structural diversity of carbohydrate antigens of selected Gram-negative marine bacteria" -
Marine Drugs 9(10) (2011) 1914-1954
Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobacteria phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.
O-specific polysaccharides, carbohydrate antigens, marine microorganisms
NCBI PubMed ID: 22073003Publication DOI: 10.3390/md9101914Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: elnaz@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia, Faculty of Life and Social Sciences, Swinburne University of Technology, PO Box 218, Hawthorn, Victoria 3122, Australia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, mild acid hydrolysis, HPAEC, ESI-FTICR-MS, Smith degradation, chemical methods, MALDI-TOF MS, MS, de-O-acetylation, NMR-1D, GPC, alkaline hydrolysis, periodate oxidation, CE-ESI-MS, CE-MS, hydrazinolysis
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10. Compound ID: 2756
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b-D-Galp-(1-6)-+
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-3)-b-D-Galp-(1-3)-b-D-Glcp-(1-3)-a-D-GalNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 967
Marshall VM, Laws AP, Gu Y, Levander F, Radstrom P, De Vuyst L, Degeest B, Vaningelgem F, Dunn H, Elvin M "Exopolysaccharide-producing strains of thermophilic lactic acid bacteria cluster into groups according to their EPS structure" -
Letters in Applied Microbiology 32(6) (2001) 433-437
AIMS: To compare galactose-negative strains of Streptococcus thermophilus and Lactobacillus delbrueckii subspecies bulgaricus isolated from fermented milk products and known to produce exopolysaccharides (EPSs). METHODS AND RESULTS: The structures of the EPSs were determined using nuclear magnetic resonance (NMR) and their genetic relationships determined using restriction endonuclease analysis (REA) and random amplification of polymorphic DNA (RAPD). Similar groupings were apparent by REA and RAPD, and each group produced an EPS with a particular subunit structure. CONCLUSION: Although none of the strains assimilated galactose, all inserted a high proportion of galactose into their EPS when grown in skimmed milk, and fell into three distinct groups. Significance and Impact of the Study: This information should help in an understanding of genetic exchanges in lactic acid bacteria
structure, Lactic acid bacteria, Streptococcus thermophilus, cluster, exopolysaccharides, Lactobacillus, classification, Lactobacillus delbrueckii, Streptococcus thermophilusstructure
NCBI PubMed ID: 11412358Journal NLM ID: 8510094Correspondence: v.m.marshall@hud.ac.uk
Institutions: Centre for Biomolecular Sciences, University of Huddersfield, UK
Methods: NMR
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11. Compound ID: 2844
|
a-L-Fucp-(1-2)-+
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a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1--/lipopolysacharide core/ |
Show graphically |
Structure type: oligomer
Aglycon: lipopolysacharide core
Trivial name: monofucosyl A type 1 histo-blood group epitope
Contained glycoepitopes: IEDB_130648,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1003
Monteiro MA, Zheng PY, Appelmelk BJ, Perry MB "The lipopolysaccharide of Helicobacter mustelae type strain ATCC43772 expresses the monofucosyl A type 1 histo-blood group epitope" -
FEMS Microbiology Letters 154(1) (1997) 103-109
Lipopolysaccharide, LPS, structure, strain, O-antigen, group, structural determination, epitope, type, molecular mimicry, Helicobacter mustelae, Helicobacter, blood group A
Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: Mario.Monteiro@nrc.ca
Institutions: Canadian Bacterial Diseases Network, Institute for Biological Sciences,National Research Council Canada,Ottawa,Canada
Methods: NMR, MS
- Article ID: 4690
Knirel YA, Gabius H, Blixt O, Rapoport EM, Khasbiullina NR, Shilova NV, Bovin NV "Human tandem-repeat-type galectins bind bacterial non-bGal polysaccharides" -
Glycoconjugate Journal 31(1) (2014) 7-12
Galectins are multifunctional effectors, for example acting as regulators of cell growth via protein-glycan interactions. The observation of capacity to kill bacteria for two tandem-repeat-type galectins, which target histo-blood epitopes toward this end (Stowell et al. Nat. Med. 16:295-301, 2010), prompted us to establish an array with bacterial polysaccharides. We addressed the question whether sugar determinants other than ?-galactosides may be docking sites, using human galectins-4, -8, and -9. Positive controls with histo-blood group ABH-epitopes and the E. coli 086 polysaccharide ascertained the suitability of the set-up. Significant signal generation, depending on type of galectin and polysacchride, was obtained. Presence of cognate ?-galactoside-related epitopes within a polysaccharide chain or its branch will not automatically establish binding properties, and structural constellations lacking galactosides, like rhamnan, were found to be active. These data establish the array as valuable screening tool, giving direction to further functional and structural studies.
glycan, Bacterial polysaccharide, ABO, galectin, printed glycan array, rhamnoside
NCBI PubMed ID: 24065176Publication DOI: 10.1007/s10719-013-9497-3Journal NLM ID: 8603310WWW link: doi:10.1007/s10719-013-9497-3Publisher: Kluwer Academic Publishers
Correspondence: bovin@carb.ibch.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, Moscow, Russian Federation, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10
Methods: GPC, mild acid degradation, binding assays
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12. Compound ID: 2852
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| |
a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140088,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_146664,IEDB_149568,IEDB_150899,IEDB_151531,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_885822,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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13. Compound ID: 2853
|
a-L-Fucp-(1-2)-+ a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+ EtN-(1--P--7)--+
| | |
a-D-GalpNAc-(1-3)-b-D-Gal-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 monofucosyl A blood-group determinant
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130652,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140088,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_885822,IEDB_983931,SB_100,SB_137,SB_149,SB_154,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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14. Compound ID: 2854
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-L-Fucp-(1-4)-+ |
| |
a-L-Fucp-(1-2)-+ | | EtN-(1--P--7)--+
| | | |
a-D-GalpNAc-(1-3)-b-D-Gal-(1-3)-b-D-GlcpNAc-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: type 1 difucosyl A blood-group determinant
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130652,IEDB_130653,IEDB_131182,IEDB_135813,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137340,IEDB_137354,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391962,IEDB_140088,IEDB_140124,IEDB_141584,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_142489,IEDB_143794,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_149554,IEDB_149556,IEDB_149568,IEDB_150899,IEDB_150948,IEDB_151531,IEDB_152213,IEDB_152214,IEDB_152218,IEDB_153205,IEDB_153223,IEDB_153536,IEDB_153553,IEDB_153554,IEDB_157005,IEDB_174039,IEDB_174333,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423096,IEDB_461709,IEDB_461712,IEDB_461719,IEDB_461723,IEDB_461724,IEDB_885822,IEDB_983931,SB_100,SB_102,SB_137,SB_146,SB_149,SB_154,SB_155,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_86,SB_88
The structure is contained in the following publication(s):
- Article ID: 1005
Monteiro MA, Zheng P, Ho B, Yokota S, Amano K, Pan Z, Berg DE, Chan KH, MacLean LL, Perry MB "Expression of histo-blood group antigens by lipopolysaccharides of Helicobacter pylori strains from Asian hosts: the propensity to express type 1 blood-group antigens" -
Glycobiology 10(7) (2000) 701-713
Past studies have shown that the cell surface lipopolysaccharides (LPSs) of the ubiquitous human gastric pathogen Helicobacter pylori (a type 1 carcinogen) isolated from people residing in Europe and North America express predominantly type 2 Lewis x (Le(x)) and Le(y) epitopes and, infrequently, type 1 Le(a), Le(b), and Le(d) antigens. This production of Lewis blood-group structures by H. pylori LPSs, similar to those found in the surfaces of human gastric cells, allows the bacterium to mimic its human niche. In this study, LPSs of H.pylori strains extracted from patients living in China, Japan, and Singapore were chemically and serologically analyzed. When compared with Western H.pylori LPSs, these Asian strains showed a stronger tendency to produce type 1 blood groups. Of particular interest, and novel observations in H.pylori, the O-chain regions of strains F-58C and R-58A carried type 1 Le(a) without the presence of type 2 Le(x), strains R-7A and H607 were shown to have the capability of producing the type 1 blood group A antigen, and strains CA2, H507, and H428 expressed simultaneously the difucosyl isomeric antigens, type 1 Le(b) and type 2 Le(y). The apparent proclivity for the production of type 1 histo-blood group antigens in Asian H.pylori LPSs, as compared with Western strains, may be an adaptive evolutionary effect in that differences in the gastric cell surfaces of the respective hosts might be significantly dissimilar to select for the formation of different LPS structures on the resident H.pylori strain.
lipopolysaccharides, structural determination, Helicobacter pylori, histo-blood groups
NCBI PubMed ID: 10910974Publication DOI: 10.1093/glycob/10.7.701Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Institute for Biological Sciences, National Research Council, Ottawa, Canada, Department of Microbiology, National University of Singapore, Singapore, Central Research Laboratory, Akita University School of Medicine, Akita, Japan, Departments of Molecular Microbiology and Genetics, Washington University School of Medicine, St. Louis, MO 63130, USA
Methods: FAB-MS, NMR
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15. Compound ID: 2913
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a-D-Galp-(1-6)-+
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-3)-a-D-GalpNAc-(1-3)-b-D-Galp-(1-3)-b-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
; 1370000
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_140529,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_152213,IEDB_153205,IEDB_167069,IEDB_190606,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1044
Navarini L, Abatangelo A, Bertocchi C, Conti E, Bosco M, Picotti F "Isolation and characterization of the exopolysaccharide produced by Streptococcus thermophilus SFi20" -
International Journal of Biological Macromolecules 28(3) (2001) 219-226
This paper reports isolation, structural characterization and some physico-chemical properties in aqueous solution of the exopolysaccharide (EPS) produced by Streptococcus thermophilus strain SFi20. The yield of the purified EPS was found to be reproducible and close to the average value of 143 mg/l. The chemical structure, previously suggested, has been confirmed on the basis of NMR data. Viscometric, chiro-optical and rheological measurements have been carried out with the aim of characterizing the conformational state of the polysaccharide in aqueous solution. All the data reported indicate that the EPS does not undergo a cooperative conformational transition under the investigated experimental conditions. Furthermore, the viscosity data and the viscoelastic behaviour suggest that the polymer is rather flexible and adopts a random coil conformation in aqueous solution
characterization, Streptococcus thermophilus, exopolysaccharide, isolation
NCBI PubMed ID: 11251229Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: navarini@polytech3.area.trieste.it
Institutions: POLY-tech s.c.a.r.l., AREA Science Park, Padriciano 99, I- 34012 Trieste, Italy.
Methods: NMR, viscosity measurement, rheological measurements, chiro-optical measurements
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