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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_142345,IEDB_151771,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 135
  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.

  T cell, polysaccharides, structure/function

  NCBI PubMed ID: 14670714
  Publication DOI: 10.1016/j.carres.2003.06.005
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: atzianabos@channing.harvard.edu
  Institutions: Department of Medicine, Channing Laboratory, 181 Longwood Ave., Brigham and Women's Hospital, Boston, MA 02115, USA
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 5248 (all data & tools)
• Article ID: 136
  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.13.4.523-533.2000
  Journal NLM ID: 8807282
  Publisher: 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
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 5250 (all data & tools)
• Article ID: 1767
  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: 1567854
  Publication DOI: 10.1021/bi00131a026
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario
  Methods: 13C NMR, 1H NMR, 31P NMR
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 107776 (all data & tools)
• Article ID: 2552
  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: 0246127
  Publisher: American Society for Microbiology
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 130556 (all data & tools)
• Article ID: 2661
  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: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 136384 (all data & tools)
• Article ID: 2809
  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: 0404511
  Publisher: Washington, DC: American Association for the Advancement of Science
  
   
  
  Bacteroides fragilis
  CSDB ID 148367 (all data & tools)
• Article ID: 3307
  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: 7927768
  Journal NLM ID: 0246127
  Publisher: 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
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 22441 (all data & tools)
• 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: 32679340
  Publication DOI: 10.1016/j.carres.2020.108045
  Journal NLM ID: 0043535
  Publisher: 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
  
   
  
  Bacteroides fragilis
  CSDB ID 4192 (all data & tools)
• 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/B978-0-12-819475-1.00005-5
  Publisher: 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
  
   
  
  Bacteroides fragilis NCTC 9343
  CSDB ID 7019 (all data & tools)
• 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: 33843231
  Publication DOI: 10.1021/acs.joc.0c02935
  Journal NLM ID: 2985193R
  Publisher: 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
  
   
  
  Bacteroides fragilis NCTC 9343 A1
  CSDB ID 10921 (all data & tools)
• 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, glycoconjugates, glycan, polysaccharides, Gram-negative bacteria, gram-positive bacteria

  NCBI PubMed ID: 34905344
  Publication DOI: 10.1021/acs.chemrev.1c00729
  Journal NLM ID: 2985134R
  Publisher: 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
  
   
  
  Bacteroides fragilis
  CSDB ID 20833 (all data & tools)
• 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: 36354960
  Publication DOI: 10.1021/jacs.2c05953
  Journal NLM ID: 7503056
  Publisher: 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
  
   
  
  Bacteroides fragilis
  CSDB ID 21136 (all data & tools)
• 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: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: 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
  
   
  
  Bacteroides fragilis
  CSDB ID 9130 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: zwitterionic polysaccharide A1
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141794,IEDB_142345,IEDB_151771,IEDB_152213,IEDB_153205,IEDB_190606,IEDB_885822,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• 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: 33843231
  Publication DOI: 10.1021/acs.joc.0c02935
  Journal NLM ID: 2985193R
  Publisher: 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
  
   
  
  Bacteroides fragilis NCTC 9343 A1
  CSDB ID 9722 (all data & tools)