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1. Compound ID: 130
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b-D-Galp-(1-6)-b-D-Galp-(1-4)-+
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-3)-a-D-Galp-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130669,IEDB_133754,IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_225177,IEDB_742246,IEDB_885823,IEDB_918313,SB_165,SB_166,SB_187,SB_195,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 26
Bubb WA, Urashima T, Fujiwara R, Shinnai T, Ariga H "Structural characterization of the extracellular polysaccharide produced by Streptococcus thermophilus OR 901" -
Carbohydrate Research 301(1-2) (1997) 41-50
The exocellular polysaccharide of Streptococcus thermophilus OR 901, isolated from partially deproteinised whey, is a heteropolymer of D-galactopyranose and L-rhamnopyranose residues in the molar ratio 5:2. The structure was established by methylation analysis and 1D and 2D NMR spectroscopy of the native polysaccharide, in combination with characterisation of oligosaccharide fragments, obtained by partial acid hydrolysis, using methylation analysis and 1D 1H NMR spectroscopy. The polysaccharide has a branched heptasaccharide repeating unit with the following structure: [structure]
Lactic acid bacteria, Streptococcus thermophilus, Exopolysaccharide structure, NMR data
NCBI PubMed ID: 9228738Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: wab@biochem.usyd.edu.au
Institutions: Department of Biochemistry, University of Sydney, NSW, Australia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, acid hydrolysis
- Article ID: 62
Faber EJ, Zoon P, Kamerling JP, Vliegenthart JFG "The exopolysaccharides produced by Streptococcus thermophilus Rs and Sts have the same repeating unit but differ in viscosity of their milk cultures" -
Carbohydrate Research 310(4) (1998) 269-276
The polysaccharides produced by Streptococcus thermophilus Rs and Sts in skimmed milk consist of D-Gal and L-Rha in a molar ratio of 5:2. Linkage analysis and 1D/2D NMR (1H and 13C) studies revealed that both polysaccharides have the same branched heptasaccharide repeating unit: [formula: see text] Remarkably, the two strains differ in their effects on the viscosity of stirred milk cultures. The milk culture of S. thermophilus Rs is non-ropy and affords 135 mg/L polysaccharide with an average molecular mass of 2.6 x 10(3) kDa. In contrast, the milk culture of S. thermophilus Sts is ropy and produces 127 mg/L polysaccharide with an average molecular mass of 3.7 x 10(3) kDa. Permeability measurements of non-stirred milk cultures of both strains suggest that both strains have a similar effect on the protein-polysaccharide network. Therefore, the only clear difference between both strains, which may cause the difference in ropiness of the milk cultures, is the difference in molecular mass of the polysaccharide
Streptococcus thermophilus, exopolysaccharide, ropiness, permeability, viscosity
NCBI PubMed ID: 9821263Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: kame@boc.chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands
Methods: methylation, NMR-2D, NMR, sugar analysis
- Article ID: 922
Leeflang BR, Faber EJ, Erbel P, Vliegenthart JFG "Structure elucidation of glycoprotein glycans and of polysaccharides by NMR spectroscopy" -
Journal of Biotechnology 77(1) (2000) 115-122
The applicability of 1H NMR spectroscopy for the determination of the primary and tertiary structure of carbohydrate-containing molecules is demonstrated. For classes of known compounds the characterization can be based on chemical shifts observed in 1D NMR spectra with or without the aid of a computer database. For more complex structure determinations 2D NMR techniques are required. Here the application of 2D NMR is demonstrated for the primary structure determination of two bacterial exopolysaccharides, for the spatial structure determination of a disaccharide and a glycoprotein hormone.
NMR, structure, polysaccharide, NMR spectroscopy, glycan, structure elucidation, polysaccharides, spectroscopy, elucidation, glycoprotein, glycoprotein glycans
NCBI PubMed ID: 10674218Journal NLM ID: 8411927Publisher: Amsterdam: Elsevier
Correspondence: b.r.leeflang@chem.uu.nl
Institutions: Bijvoet Center for Biomolecular Research, Utrecht University, Utrecht, The Netherlands
Methods: NMR-2D, NMR
- Article ID: 3406
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: 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, Lactic acid bacteria, exopolysaccharides, polysaccharides, 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: 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, methylation, NMR-2D, GC-MS, acid hydrolysis, HPLC, function analysis of gene clusters, yogurt production, yogurt quality evaluation
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2. Compound ID: 132
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 26
Bubb WA, Urashima T, Fujiwara R, Shinnai T, Ariga H "Structural characterization of the extracellular polysaccharide produced by Streptococcus thermophilus OR 901" -
Carbohydrate Research 301(1-2) (1997) 41-50
The exocellular polysaccharide of Streptococcus thermophilus OR 901, isolated from partially deproteinised whey, is a heteropolymer of D-galactopyranose and L-rhamnopyranose residues in the molar ratio 5:2. The structure was established by methylation analysis and 1D and 2D NMR spectroscopy of the native polysaccharide, in combination with characterisation of oligosaccharide fragments, obtained by partial acid hydrolysis, using methylation analysis and 1D 1H NMR spectroscopy. The polysaccharide has a branched heptasaccharide repeating unit with the following structure: [structure]
Lactic acid bacteria, Streptococcus thermophilus, Exopolysaccharide structure, NMR data
NCBI PubMed ID: 9228738Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: wab@biochem.usyd.edu.au
Institutions: Department of Biochemistry, University of Sydney, NSW, Australia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, acid hydrolysis
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3. Compound ID: 133
Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 26
Bubb WA, Urashima T, Fujiwara R, Shinnai T, Ariga H "Structural characterization of the extracellular polysaccharide produced by Streptococcus thermophilus OR 901" -
Carbohydrate Research 301(1-2) (1997) 41-50
The exocellular polysaccharide of Streptococcus thermophilus OR 901, isolated from partially deproteinised whey, is a heteropolymer of D-galactopyranose and L-rhamnopyranose residues in the molar ratio 5:2. The structure was established by methylation analysis and 1D and 2D NMR spectroscopy of the native polysaccharide, in combination with characterisation of oligosaccharide fragments, obtained by partial acid hydrolysis, using methylation analysis and 1D 1H NMR spectroscopy. The polysaccharide has a branched heptasaccharide repeating unit with the following structure: [structure]
Lactic acid bacteria, Streptococcus thermophilus, Exopolysaccharide structure, NMR data
NCBI PubMed ID: 9228738Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: wab@biochem.usyd.edu.au
Institutions: Department of Biochemistry, University of Sydney, NSW, Australia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, acid hydrolysis
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4. Compound ID: 1027
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L-Fucp-(1-3)-+
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b-D-Galp-(1-6)-b-D-Galp-(1-4)-+ |
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-2)-a-D-Galp-(1-3)-a-D-Galp-(1-3)-a-D-Galp-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130669,IEDB_133754,IEDB_136044,IEDB_136045,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_151528,IEDB_152214,IEDB_153201,IEDB_156493,IEDB_174333,IEDB_190606,IEDB_225177,IEDB_742246,IEDB_885823,IEDB_918313,SB_165,SB_166,SB_187,SB_195,SB_7,SB_86,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 312
Low D, Ahlgren JA, Horne D, McMahon DJ, Oberg CJ, Broadbent JR "Role of Streptococcus thermophilus MR-1C capsular exopolysaccharide in cheese moisture retention" -
Applied and Environmental Microbiology 64(6) (1998) 2147-2151
Recent work by our group has shown that an exopolysaccharide (EPS)-producing starter pair, Streptococcus thermophilus MR-1C and Lactobacillus delbrueckii subsp. bulgaricus MR-1R, can significantly increase moisture retention in low-fat mozzarella (D. B. Perry, D. J. McMahon, and C. J. Oberg, J. Dairy Sci. 80:799-805, 1997). The objectives of this study were to determine whether MR-1C, MR-1R, or both of these strains are required for enhanced moisture retention and to establish the role of EPS in this phenomenon. Analysis of low-fat mozzarella made with different combinations of MR-1C, MR-1R, and the non-EPS-producing starter culture strains S. thermophilus TA061 and Lactobacillus helveticus LH100 showed that S. thermophilus MR-1C was responsible for the increased cheese moisture level. To investigate the role of the S. thermophilus MR-1C EPS in cheese moisture retention, the epsE gene in this bacterium was inactivated by gene replacement. Low-fat mozzarella made with L. helveticus LH100 plus the non-EPS-producing mutant S. thermophilus DM10 had a significantly lower moisture content than did cheese made with strains LH100 and MR-1C, which confirmed that the MR-1C capsular EPS was responsible for the water-binding properties of this bacterium in cheese. Chemical analysis of the S. thermophilus MR-1C EPS indicated that the polymer has a novel basic repeating unit composed of D-galactose, L-rhamnose, and L-fucose in a ratio of 5:2:1.
capsular, Streptococcus, Streptococcus thermophilus, exopolysaccharide, retention
NCBI PubMed ID: 9603827Journal NLM ID: 7605801Publisher: American Society for Microbiology
Correspondence: Broadbnt@cc.usu.edu
Institutions: Department of Nutrition and Food Sciences, Utah State University, Logan, Utah 84322-8700, Biopolymer Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, Peoria, Illinois 61604, and Department of Microbiology, Weber State University, Ogden, Utah 84408-2506
- 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, Lactic acid bacteria, exopolysaccharides, polysaccharides, 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
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5. Compound ID: 1201
Structure type: polymer chemical repeating unit
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_156557,IEDB_190606,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 375
Shashkov AS, Streshinskaia GM, Kosmachevskaia LN, Senchenkova SN, Evtushenko LI, Naumova IB "NMR-based identification of cell wall galactomannan of Streptomyces sp. VKM Ac-2125" -
Carbohydrate Research 338(19) (2003) 2021-2024
The major cell wall polymer of Streptomyces sp. VKM Ac-2125, the causative agent of potato scab, is galactomannan with the repeating unit of the following structure: [carbohydrate structure in text] The polysaccharide with such a structure is found in the bacterial cell wall for the first time. The cell wall also contains small amount of a teichoic acid of the poly(glycerol phosphate) type and 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid.
teichoic acid, Galactomannan, Kdn;, Plant pathogenic streptomycete
NCBI PubMed ID: 14499580Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: i_naumova@mail.ru; naumova@microbiol.bio.msu.su
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, School of Biology, M. V. Lomonosov Moscow State University, Moscow, Russian Federation, Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, Moscow Region 142292, Russian Federation
Methods: NMR-2D, NMR
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6. Compound ID: 1893
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-6)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galf-(1-3)-b-D-Glcp-(1-6)-b-D-Galf-(1-6)-a-D-Galp-(1-6)-a-D-Glcp-(1-P- |
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Structure type: polymer chemical repeating unit
Trivial name: poly(glycosyl phosphate)
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_140529,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,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: 633
Bergstrom N, Jansson P, Kilian M, Sorensen UBS, Sorensen UB "Structures of two cell wall-associated polysaccharides of a Streptococcus mitis biovar 1 strain. A unique teichoic acid-like polysaccharide and the group O antigen which is a C-polysaccharide in common with pneumococci" -
European Journal of Biochemistry 267 (2000) 7147-7157
The cell wall of Streptococcus mitis biovar 1 strain SK137 contains the C-polysaccharide known as the common antigen of a closely related species Streptococcus pneumoniae, and a teichoic acid-like polysaccharide with a unique structure. The two polysaccharides are different entities and could be partially separated by gel chromatography. The structures of the two polysaccharides were determined by chemical methods and by NMR spectroscopy. The teichoic acid-like polymer has a heptasaccharide phosphate repeating unit with the following structure: -6)bDGalp(1-6)bDGalp(1-6)bDGalf(1-3)bDGlcp(1-6)bDGalf(1-6)aDGalp(1-6)aDGlcp(1-P- The structure neither contains ribitol nor glycerol phosphate as classical teichoic acids do, thus we have used the expression teichoic acid-like for this polysaccharide. The following structure of the C-polysaccharide repeating unit was established: -6)bDGlcp(1-3)aAATp(1-4)[Cho(1-P-6)]aDGalpNAc(1-3)[Cho(1-P-6)]aDGalpNAc(1-1)Rib-ol(5-P- where AAT is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose. It has a carbohydrate backbone identical to that of one of the two structures of C-polysaccharide previously identified in S. pneumoniae. C-polysaccharide of S. mitis is characterized by the presence, in each repeating unit, of two residues of phosphocholine and both galactosamine residues in the N-acetylated form. Immunochemical analysis showed that C-polysaccharide constitutes the Lancefield group O antigen. Studies using mAbs directed against the backbone and against the phosphocholine moiety of the C-polysaccharide revealed several different patterns of these epitopes among 95 S. mitis and Streptococcus oralis strains tested and the exclusive presence of the group O antigen in the majority of S. mitis biovar 1 strains.
antigen, structure, common, strain, polysaccharide, Streptococcus, O-antigen, O antigen, cell, group, form, common antigen, polysaccharides, Phosphocholine, biovar, pneumococcal, C-polysaccharide, C polysaccharide, choline, teichoic acid-like
NCBI PubMed ID: 11106426Publication DOI: 10.1046/j.1432-1327.2000.01821.x-i2Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Correspondence: pererik.jansson@kfcmail.hs.sll.se
Institutions: Clinical Research Centre, Analytical Unit, Karolinska Institute, Huddinge Hospital, Novum, Huddinge, Sweden, Department of Medical Microbiology and Immunology, University of Aarhus, Denmark
Methods: MAb studies
- Article ID: 3365
Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" -
Carbohydrate Research 342(3-4) (2007) 297-344
An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).
synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters
NCBI PubMed ID: 17092493Publication DOI: 10.1016/j.carres.2006.10.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: a.v.nikolaev@dundee.ac.uk
Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
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7. Compound ID: 3066
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L-gro-a-D-manHepp-(1-7)-+
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a-D-Galp-(1-6)-+ |
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D-Galp-(1-6)-D-Galp-(1-4)-D-GlcpNAc-(1-3)-D-Galp-(1-3)-D-GlcpNAc-(1-7)-L-gro-a-D-manHepp-(1-6)-a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-a-D-Glcp-(1-3)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130646,IEDB_130650,IEDB_130670,IEDB_130697,IEDB_134624,IEDB_135813,IEDB_136044,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391962,IEDB_140088,IEDB_140108,IEDB_140122,IEDB_140529,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_143794,IEDB_144998,IEDB_145003,IEDB_146664,IEDB_150899,IEDB_151528,IEDB_151531,IEDB_153201,IEDB_156493,IEDB_167070,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_232584,IEDB_742248,IEDB_983931,SB_137,SB_163,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_29,SB_30,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1109
Phillips NJ, Miller TJ, Engstrom JJ, Melaugh W, McLaughlin R, Apicella MA, Gibson BW "Characterization of chimeric lipopolysaccharides from Escherichia coli strain JM109 transformed with lipooligosaccharide synthesis genes (lsg) from Haemophilus influenzae" -
Journal of Biological Chemistry 275(7) (2000) 4747-4758
Previously, we reported the expression of chimeric lipopolysaccharides (LPS) in Escherichia coli strain JM109 (a K-12 strain) transformed with plasmids containing Haemophilus influenzae lipooligosaccharide synthesis genes (lsg) (Abu Kwaik, Y., McLaughlin, R. E., Apicella, M. A., and Spinola, S. M. (1991) Mol. Microbiol. 5, 2475-2480). In this current study, we have analyzed the O-deacylated LPS and free oligosaccharides from three transformants (designated pGEMLOS-4, pGEMLOS-5, and pGEMLOS-7) by matrix-assisted laser desorption ionization, electrospray ionization, and tandem mass spectrometry techniques, along with composition and linkage analyses. These data show that the chimeric LPS consist of the complete E. coli LPS core structure glycosylated on the 7-position of the non-reducing terminal branch heptose with oligosaccharides from H. influenzae. In pGEMLOS-7, the disaccharide Gal 1→3 GlcNAc1→ is added, and in pGEMLOS-5, the structure is extended to Gal 1→4 GlcNAc 1→3 Gal 1→3 GlcNAc1→. PGEMLOS-5 LPS reacts positively with monoclonal antibody 3F11, an antibody that recognizes the terminal disaccharide of lacto-N-neotetraose. In pGEMLOS-4 LPS, the 3F11 epitope is apparently blocked by glycosylation on the 6-position of the terminal Gal with either Gal or GlcNAc. The biosynthesis of these chimeric LPS was found to be dependent on a functional wecA (formerly rfe) gene in E. coli. By using this carbohydrate expression system, we have been able to examine the functions of the lsg genes independent of the effects of other endogenous Haemophilus genes and expressed proteins.
Lipopolysaccharide, synthesis, Haemophilus, Haemophilus influenzae, lipopolysaccharides, Lipooligosaccharide, gene, strain, characterization, Escherichia, Escherichia coli
NCBI PubMed ID: 10671507Publication DOI: 10.1074/jbc.275.7.4747Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: gibson@socrates.cgl.ucsf.edu
Institutions: Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA, Department of Microbiology, University of Iowa, Iowa City, Iowa 52242, Department of Microbiology, University of Oklahoma Health Sciences Center, Oklahoma City, Oklahoma 73104
Methods: ESI-MS, MALDI-MS, MS/MS, composition analysis, linkage analysis
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8. Compound ID: 3156
|
D-Gro-(3--P--3)--+
|
-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_147450,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 1150
Robijn GW, Wienk HLJ, van den Berg DJC, Haas H, Kamerling JP, Vliegenthart JFG "Structural studies of the exopolysaccharide produced by Lactobacillus paracasei 34-1" -
Carbohydrate Research 285 (1996) 129-139
The exopolysaccharide produced by Lactobacillus paracasei 34-1 in a semi-defined medium was found to be a heteropolymer, composed of D-galactose, 2-acetamido-2-deoxy-D-galactose, and sn-glycerol 3-phosphate in molar ratios of 3:1:1. By means of deglycerophosphorylation, methylation analysis, and 1D/2D NMR studies (1H, 13C, and 31P) the polysaccharide was shown to consist of repeating units with the following structure: [formula]
structural, phosphate, Lactic acid bacteria, exopolysaccharide, structural studies, Lactobacillus, lactic acid bacterium, glycerol, Lb. paracasei, phosphoglycerol
NCBI PubMed ID: 9011373Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Unilever Research Laboratarv Vlaardingen, P.O. Box 114, NL-3130 AC Vlaardingen, The Netherlands
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9. Compound ID: 3157
|
-3)-b-D-GalpNAc-(1-4)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130648,IEDB_134627,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_147450,IEDB_153201,IEDB_156489,IEDB_156493,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_23,SB_24,SB_25,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 1150
Robijn GW, Wienk HLJ, van den Berg DJC, Haas H, Kamerling JP, Vliegenthart JFG "Structural studies of the exopolysaccharide produced by Lactobacillus paracasei 34-1" -
Carbohydrate Research 285 (1996) 129-139
The exopolysaccharide produced by Lactobacillus paracasei 34-1 in a semi-defined medium was found to be a heteropolymer, composed of D-galactose, 2-acetamido-2-deoxy-D-galactose, and sn-glycerol 3-phosphate in molar ratios of 3:1:1. By means of deglycerophosphorylation, methylation analysis, and 1D/2D NMR studies (1H, 13C, and 31P) the polysaccharide was shown to consist of repeating units with the following structure: [formula]
structural, phosphate, Lactic acid bacteria, exopolysaccharide, structural studies, Lactobacillus, lactic acid bacterium, glycerol, Lb. paracasei, phosphoglycerol
NCBI PubMed ID: 9011373Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands, Unilever Research Laboratarv Vlaardingen, P.O. Box 114, NL-3130 AC Vlaardingen, The Netherlands
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10. Compound ID: 3376
|
b-D-Galp-(1-6)-+
|
-6)-b-D-Galp-(1-4)-a-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_241101,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 1252
Staaf M, Widmalm G, Yang Z, Huttunen E "Structural elucidation of an extracellular polysaccharide produced by Lactobacillus helveticus" -
Carbohydrate Research 291 (1996) 155-164
An extracellular polysaccharide produced by a strain of Lactobacillus helveticus isolated from cheese milk has been investigated. Sugar and methylation analysis together with 1H and 13C NMR spectroscopy revealed that the polysaccharide is composed of hexasaccharide repeating units. The sequence of sugar residues was determined by use of two-dimensional nuclear Overhauser effect spectroscopy and heteronuclear multiple-bond correlation experiments. The structure of the repeating unit of the exopolysaccharide from L. helveticus is as follows: [sequence: see text]
NMR, structure, structural, polysaccharide, determination, NMR spectroscopy, exopolysaccharide, Lactobacillus helveticus, extracellular polysaccharide, spectroscopy, elucidation, Lactobacillus, extracellular, D-glucose, D-galactose
NCBI PubMed ID: 8864228Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, S-10691, Sweden, Department of Food Technology, Dairy Science, University of Helsinki, Helsinki, Finland
Methods: methylation, NMR-2D, NMR
- 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: 6264
Lebrilla CB, Liu J, Widmalm G, Prestegard JH "Oligosaccharides and Polysaccharides" -
Book: Essentials of Glycobiology [Internet]. 4rd edition. (2022)
This chapter discusses the diversity in structure and properties that results when multiple monosaccharides (Chapter 2) are linked together to form oligosaccharides and polysaccharides (the latter comprising much of the biomass on the planet). Some examples of the more complex polymeric assemblies that occur in nature are presented, and how these remarkable structures are generated is discussed.
structure, polysaccharide, Oligosaccharides, polysaccharides
NCBI PubMed ID: 35536971Publication DOI: 10.1101/glycobiology.4e.3Publisher: Cold Spring Harbor (NY): Cold Spring Harbor Laboratory Press
Editors: Varki A, Cummings RD, Esko JD, Stanley P, Hart GW, Aebi M, Mohnen D, Kinoshita T, Packer NH, Prestegard JH, Schnaar RL, Seeberger RH
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11. Compound ID: 3473
|
S-Pyr-(2-4:2-3)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Glcp-(1-6)-a-D-Galp-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1-4)-b-D-Glcp-(1-6)-+
|
-4)-b-D-GlcpA-(1-4)-b-D-GlcpA-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_423153,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: 1332
Ziegler T, Eckhardt E, Keller D "Rhizobial saccharides. 3. Unexpected a-selective glycosylation during synthesis of pyruvated tetrasaccharide fragments related to exopolysaccharides of Rhizobium leguminosarum" -
Journal of Carbohydrate Chemistry 16(6) (1997) 719-738
The two diastereomeric tetraccharide allyl glycosides related to the exopolysaccharide of Rhizobium leguminosarum biovar phaseoli 127 K 87 having an (R-) and (S-)-configurated pyruvic acid acetal, repsectively at position 3 and 4 ofthe galactopyranosyl residue of the non-reducing end, were prepared from two disaccharide blocks. The fully benzoylated diastereomeric disaccharide donors having the structure 3,4-Py-bDGalp(1-6)aDGalp(1-X) with leaving group X = bromide and trichloroacetimidate were synthesised by a stepwise approach from benzoylated 3,4-pyruvated galactosyl donors (clorides, bromides, trichloroacetimidates) and benzyl and phenyl 1-thio-2,3,4-tri-O-benzoyl-b-D-galactopyranosides, respectively. The disaccharide acceptorshaving the structure bDGlcp(1-6)aDGalp(1-O-allyl) were obtained by coupling allyl 2,3,4-tri-O-benzoyl-a-D-galactopyranoside and its 6-O-trimethylsilyl ether with suitably protected glucosyl chlorides or fluorides. The coupling of the pyruvated disaccharide trichloroacetimidates with the disaccharide acceptors afforded the b(1-6)linked tetrasaccharides whereas the coupling of the pyruvated disaccharide bromide resulted in an a(1-6)selective glycosylation. The anomeric selectivity was attributed to a double diastereoselection caused by the configuration of pyruvic acid acetal. Deblocking of three tetrasaccharides provided the corresponding tetrasaccharide allyl glycosides which are suitable for preparation of glycoconjugates
synthesis, tetrasaccharide, Rhizobia, Rhizobium, exopolysaccharide, exopolysaccharides, fragment, Rhizobium leguminosarum, glycosylation, saccharide, saccharides
Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Institute of Organic Chemistry, University of Cologne, Greinstrasse 4, D-50939, Koeln, Germany
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12. Compound ID: 3499
Structure type: polymer chemical repeating unit
Trivial name: SP-PG
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_221845,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 1290
Yamazaki K, Inukai K, Suzuki M, Kuga H, Korenaga H "Structural studies on a sulfated polysaccharide from an Arthrobacter sp. by NMR spectroscopy and methylation analysis" -
Carbohydrate Research 305(2) (1997) 253-260
Structural characterization of a sulfated polysaccharide peptidoglycan complex (SP-PG) from an Arthrobacter sp. was performed by NMR spectroscopy and methylation analysis. In order to simplify the analyses, the desulfated SP-PG was used. NMR spectroscopy revealed the presence of a trisaccharide repeating unit and a disaccharide repeating unit. The trisaccharide unit was composed of two galactofuranosides and one glucopyranoside, and the disaccharide unit was of two galactopyranosides, as shown below. The methylation analysis showed that the polysaccharide consists mainly of a 4-linked galactopyranoside, a 6-linked galactopyranoside, a 6-linked galactofuranoside, a 2,6-linked galactofuranoside, a terminal galactopyranoside and a terminal glucopyranoside. These findings confirmed the structure indicated by the NMR spectroscopy. The repeating units determined in this study are novel
methylation analysis, cell wall, 2D NMR, Arthrobacter sp., Sulfated glucogalactan
NCBI PubMed ID: 9581278Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: vamaz33x@daiichipharm.co.jp
Institutions: Basic Technology Research Laboratory, Daiichi Pharmaceutical, 16-13, Kitakasai l-Chome,Edogawa-ku, Tokyo 134, Japan, Drug Metabolism and Analytical Chemistry, Research Laboratory, Daiichi Pharmaceutical, 16-13, Kitakasai 1-Chome, Edogawa-ku, Tokyo 134, Japan, New Product Research Laboratory, IV, Daiichi Pharmaceutical, 16-13, Kitakasai l-Chome, Edogawa-ku, Tokyo 134, Japan
Methods: methylation, NMR-2D, NMR
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13. Compound ID: 3584
|
S-Pyr-(2-4:2-3)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Glcp-(1-6)-a-D-Galp-(1-1)-Allyl |
Show graphically |
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_153201,IEDB_156493,IEDB_190606,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: 1332
Ziegler T, Eckhardt E, Keller D "Rhizobial saccharides. 3. Unexpected a-selective glycosylation during synthesis of pyruvated tetrasaccharide fragments related to exopolysaccharides of Rhizobium leguminosarum" -
Journal of Carbohydrate Chemistry 16(6) (1997) 719-738
The two diastereomeric tetraccharide allyl glycosides related to the exopolysaccharide of Rhizobium leguminosarum biovar phaseoli 127 K 87 having an (R-) and (S-)-configurated pyruvic acid acetal, repsectively at position 3 and 4 ofthe galactopyranosyl residue of the non-reducing end, were prepared from two disaccharide blocks. The fully benzoylated diastereomeric disaccharide donors having the structure 3,4-Py-bDGalp(1-6)aDGalp(1-X) with leaving group X = bromide and trichloroacetimidate were synthesised by a stepwise approach from benzoylated 3,4-pyruvated galactosyl donors (clorides, bromides, trichloroacetimidates) and benzyl and phenyl 1-thio-2,3,4-tri-O-benzoyl-b-D-galactopyranosides, respectively. The disaccharide acceptorshaving the structure bDGlcp(1-6)aDGalp(1-O-allyl) were obtained by coupling allyl 2,3,4-tri-O-benzoyl-a-D-galactopyranoside and its 6-O-trimethylsilyl ether with suitably protected glucosyl chlorides or fluorides. The coupling of the pyruvated disaccharide trichloroacetimidates with the disaccharide acceptors afforded the b(1-6)linked tetrasaccharides whereas the coupling of the pyruvated disaccharide bromide resulted in an a(1-6)selective glycosylation. The anomeric selectivity was attributed to a double diastereoselection caused by the configuration of pyruvic acid acetal. Deblocking of three tetrasaccharides provided the corresponding tetrasaccharide allyl glycosides which are suitable for preparation of glycoconjugates
synthesis, tetrasaccharide, Rhizobia, Rhizobium, exopolysaccharide, exopolysaccharides, fragment, Rhizobium leguminosarum, glycosylation, saccharide, saccharides
Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Institute of Organic Chemistry, University of Cologne, Greinstrasse 4, D-50939, Koeln, Germany
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14. Compound ID: 3585
|
R-Pyr-(2-4:2-3)-b-D-Galp-(1-6)-b-D-Galp-(1-6)-b-D-Glcp-(1-6)-a-D-Galp-(1-1)-Allyl |
Show graphically |
Structure type: oligomer
Compound class: EPS
Contained glycoepitopes: IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_151771,IEDB_153201,IEDB_156493,IEDB_190606,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: 1332
Ziegler T, Eckhardt E, Keller D "Rhizobial saccharides. 3. Unexpected a-selective glycosylation during synthesis of pyruvated tetrasaccharide fragments related to exopolysaccharides of Rhizobium leguminosarum" -
Journal of Carbohydrate Chemistry 16(6) (1997) 719-738
The two diastereomeric tetraccharide allyl glycosides related to the exopolysaccharide of Rhizobium leguminosarum biovar phaseoli 127 K 87 having an (R-) and (S-)-configurated pyruvic acid acetal, repsectively at position 3 and 4 ofthe galactopyranosyl residue of the non-reducing end, were prepared from two disaccharide blocks. The fully benzoylated diastereomeric disaccharide donors having the structure 3,4-Py-bDGalp(1-6)aDGalp(1-X) with leaving group X = bromide and trichloroacetimidate were synthesised by a stepwise approach from benzoylated 3,4-pyruvated galactosyl donors (clorides, bromides, trichloroacetimidates) and benzyl and phenyl 1-thio-2,3,4-tri-O-benzoyl-b-D-galactopyranosides, respectively. The disaccharide acceptorshaving the structure bDGlcp(1-6)aDGalp(1-O-allyl) were obtained by coupling allyl 2,3,4-tri-O-benzoyl-a-D-galactopyranoside and its 6-O-trimethylsilyl ether with suitably protected glucosyl chlorides or fluorides. The coupling of the pyruvated disaccharide trichloroacetimidates with the disaccharide acceptors afforded the b(1-6)linked tetrasaccharides whereas the coupling of the pyruvated disaccharide bromide resulted in an a(1-6)selective glycosylation. The anomeric selectivity was attributed to a double diastereoselection caused by the configuration of pyruvic acid acetal. Deblocking of three tetrasaccharides provided the corresponding tetrasaccharide allyl glycosides which are suitable for preparation of glycoconjugates
synthesis, tetrasaccharide, Rhizobia, Rhizobium, exopolysaccharide, exopolysaccharides, fragment, Rhizobium leguminosarum, glycosylation, saccharide, saccharides
Journal NLM ID: 8218151Publisher: Marcel Dekker
Institutions: Institute of Organic Chemistry, University of Cologne, Greinstrasse 4, D-50939, Koeln, Germany
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15. Compound ID: 3643
|
b-D-Galp-(1-6)-+ a-Neup5Ac-(2-3)-+
| |
-4)-b-D-GlcpNAc-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1-3)-b-D-Glcp-(1-2)-b-D-Galp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_153201,IEDB_153218,IEDB_153543,IEDB_156493,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88
The structure is contained in the following publication(s):
- Article ID: 1363
Baker CJ, Paolett LC, Rench MA, Guttormsen H, Carey VJ, Hickman ME, Kasper DL "Use of capsular polysaccharide-tetanus toxoid conjugate vaccine for type II group B Streptococcus in healthy women" -
Journal of Infectious Diseases 182(4) (2000) 1129-1138
capsular, Streptococcus, group, type, group B Streptococcus, vaccine, conjugate, conjugate vaccine, use, toxoid
Journal NLM ID: 0413675Publisher: Oxford: Oxford University Press
Correspondence: cbaker@bcm.tmc.edu
Institutions: Dept. of Pediatrics, Baylor Coolege of Medicine, Houston,USA
- Article ID: 2632
Jennings HJ, Rosell KG, Katzenellenbogen E, Kasper DL "Structural determination of the capsular polysaccharide antigen of type II group B Streptococcus" -
Journal of Biological Chemistry 258(3) (1983) 1793-1798
The native polysaccharide antigen isolated from type II group B Streptococcus contains D-galactose, D-glucose, 2-acetamido-2-deoxy-D-glucose, and sialic acid in the molar ratio of 3:2:1:1. The application of methylation and 13C nmr spectroscopic analyses to the native type II antigen and some of its specifically degraded products enabled the structure of the native type II antigen to be elucidated. The native type II antigen is composed of the following repeating unit: [formula in text]. Unlike the native types Ia, Ib, and III group B streptococcal polysaccharides, the native type II antigen contains terminal b-D-galactopyranosyl residues in addition to terminal sialic acid residues. The terminal sialic acid residues of the native type II antigen are also unique among those of the other group B streptococcal antigens in that they are not neuraminidase-sensitive and are attached directly to the backbone of the type II antigen.
NCBI PubMed ID: 6337145Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: The Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada KIA OR6
Methods: 13C NMR, methylation, GC-MS, Smith degradation, enzymatic degradation
- Article ID: 2802
Jennings HJ, Katzenellenbogen E, Lugowski C, Michon F, Roy R, Kasper DL "Structure, conformation and immunology of sialic acid-containing polysaccharides of human pathogenic bacteria" -
Pure and Applied Chemistry 56(7) (1984) 893-905
Capsular polysaccharides of types Ia, Ib, II and III Group B Streptococcus and groups B and C Neisseria meningitidis contain terminal sialic acid indiffrent molecular environments. Experimentation has identified sialic acid as an important factor in the virulence of these organisms and in the human antibody response to their capsular polysaccharide antigens. Although terminal sialic acid is not normally immunogenic it controls the determinants which are responsible for the production of protective antibodies. Using immunological and NMR spectroscopic techniques on the native and specifically modified polysaccharides, a number of these sialic acid-controlled determinants have been identified and located. These determinants are only formed in structures which can accommodate long-range interactions between sialic acid and other remote glycosyl residues. The carboxylate group of sialic acid is essential for these interactions to occur.
Journal NLM ID: 0376514WWW link: http://pac.iupac.org/publications/pac/pdf/1984/pdf/5607x0893.pdfPublisher: Oxford: Blackwell Scientific Publications
Institutions: Division of Biological Sciences, National Research Counci 1 of Canada, Ottawa, Canada, K1A 0R6
- Article ID: 4050
Knirel YA, Shevelev SD, Perepelov AV "Higher aldulosonic acids: components of bacterial glycans" -
Mendeleev Communications 21(4) (2011) 173-182
Recent data on the natural occurrence, chemistry, and biochemistry of C8 and C9 aldulosonic acids (3-deoxy-d-manno-oct-2-ulosonic acid, sialic acids, N-acyl derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids, and some others) as well as on the structures and biological significance of bacterial glycans containing these higher acidic monosaccharides are summarized.
structure, Bacterial, glycan, aldulosonic acid, higher acidic monosaccharides, sialic acids
Publication DOI: 10.1016/j.mencom.2011.07.001Journal NLM ID: 9425965Publisher: Moscow: Academy of Sciences of the USSR; Cambridge,UK : Royal Society of Chemistry
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4431
Ovodov YS "Bacterial capsular antigens. Structural patterns of capsular antigens" -
Biochemistry (Moscow) 71(9) (2006) 937-954
Structural patterns of bacterial capsular antigens including capsular polysaccharides and exoglycans are given in this review. In addition, the immunological activity of capsular antigens and their role in type specificity of bacteria are discussed.
structure, capsular polysaccharides, bacterial capsular antigens, bacterial exoglycans, immunological activity, type specificity
NCBI PubMed ID: 17009947Publication DOI: 10.1134/S000629790609001XJournal NLM ID: 0376536Publisher: Nauka/Interperiodica
Correspondence: ovoys@physiol.komisc.ru
Institutions: Institute of Physiology, Komi Science Center, Urals Branch of the Russian Academy of Sciences, Syktyvkar 167982, Russia
- Article ID: 4836
Berti F, Ravenscroft N "Characterization of Carbohydrate Vaccines by NMR Spectroscopy" -
Methods in Molecular Biology 1331 (2015) 189-209
Physicochemical techniques are a powerful tool for the structural characterization of carbohydrate-based vaccines. High-field Nuclear Magnetic Resonance (NMR) spectroscopy has been established as an extremely useful and robust method for tracking the industrial manufacturing process of these vaccines from polysaccharide bulk antigen through to the final formulation. Here, we describe the use of proton NMR for structural identity and conformity testing of carbohydrate-based vaccines.
carbohydrates, capsular polysaccharide, antigens, nuclear magnetic resonance spectroscopy, vaccines
NCBI PubMed ID: 26169742Publication DOI: 10.1007/978-1-4939-2874-3_12Journal NLM ID: 9214969Publisher: Springer
Correspondence: francesco.x.berti@gsk.com
Institutions: Research, GSK Vaccines, Via Fiorentina 1, 53100, Siena, Italy
- Article ID: 5440
Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Structure determination of Streptococcus suis serotypes 7 and 8 capsular polysaccharides and assignment of functions of the cps locus genes involved in their biosynthesis" -
Carbohydrate Research 473 (2019) 36-45
Streptococcus suis serotypes 7 and 8 are counted among the top six S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on these serotypes. Since S. suis serotyping system is based upon capsular polysaccharide (CPS) antigenicity and the CPS is considered a major virulence factor for encapsulated pathogens, here we determined for the first time the chemical compositions and structures of serotypes 7 and 8 CPSs. Chemical and spectroscopic data gave the following repeating unit sequences: [3)L-Rha(α1-P-2)D-Gal(α1-4)D-GlcA(β1-3)D-FucNAc4N(α1-]n for serotype 7 and [2)L-Rha(α1-P-4)D-ManNAc(β1-4)D-Glc(α1-]n for serotype 8. As serotype 8 CPS is identical to Streptococcus pneumoniae type 19F CPS, dot-blot analyses showed a strong reaction of the 19F polysaccharide with reference anti-S. suis serotype 8 rabbit serum. A correlation between S. suis serotypes 7 and 8 sequences and genes of those serotypes' loci encoding putative glycosyltransferases and polymerases responsible for the biosynthesis of the repeating units was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of the disease caused by S. suis serotypes 7 and 8.
capsular polysaccharide, carbohydrate structure, Serotype 8, Streptococcus suis, Serotype 7
NCBI PubMed ID: 30605786Publication DOI: 10.1016/j.carres.2018.12.009Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Segura
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan
Methods: 13C NMR, 1H NMR, GLC-MS, gel filtration, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, Western blotting, bioinformatic analysis
- Article ID: 5485
Paoletti LC, Kasper DL "Surface Structures of Group B Streptococcus Important in Human Immunity" -
Microbiology Spectrum 7(2) (2019) ID GPP3-0001-2017
The surface of the Gram-positive opportunistic pathogen Streptococcus agalactiae, or group B Streptococcus (GBS), harbors several carbohydrate and protein antigens with the potential to be effective vaccines. Capsular polysaccharides of all clinically-relevant GBS serotypes coupled to immunogenic proteins of both GBS and non-GBS origin have undergone extensive testing in animals that led to advanced clinical trials in healthy adult women. In addition, GBS proteins either alone or in combination have been tested in animals; a fusion protein construct has recently advanced to human clinical studies. Given our current understanding of the antigenicity and immunogenicity of the wide array of GBS surface antigens, formulations now exist for the generation of viable vaccines against diseases caused by GBS.
structure, capsular polysaccharides, group B Streptococcus, surface, vaccines, Streptococcus agalactiae, Gram-positive
NCBI PubMed ID: 30873933Publication DOI: 10.1128/microbiolspec.GPP3-0001-2017Journal NLM ID: 101634614Publisher: Washington, DC: ASM Press
Correspondence: Lawrence C. Paoletti
Institutions: Division of Immunology, Department of Microbiology and Immunobiology, Harvard Medical School, Boston, MA 02115
- Article ID: 5741
Carboni F, Adamo R "Structure-based glycoconjugate vaccine design: The example of Group B Streptococcus type III capsular polysaccharide" -
Drug Discovery Today: Technologies (2020) 23-33
Microbial surface polysaccharides are important virulence factors and targets for vaccine development. Glycoconjugate vaccines, obtained by covalently linking carbohydrates and proteins, are well established tools for prevention of bacterial infections. Elucidation of the minimal portion involved in the interactions with functional antibodies is of utmost importance for the understanding of their mechanism of induction of protective immune responses and the design of synthetic glycan based vaccines. Typically, this is achieved by combination of different techniques, which include ELISA, glycoarray, Surface Plasmon Resonance in conjunction with approaches for mapping at atomic level the position involved in binding, such as Saturation Transfer NMR and X-ray crystallography. This review provides an overview of the structural studies performed to map glycan epitopes (glycotopes), with focus on the highly complex structure of Group B Streptococcus type III (GBSIII) capsular polysaccharide. Furthermore, it describes the rational process followed to translate the obtained information into the design of a protective glycoconjugate vaccine based on a well-defined synthetic glycan epitope.
carbohydrates, glycoconjugates, group B Streptococcus, vaccines, Structural glycobiology
NCBI PubMed ID: 33388125Publication DOI: 10.1016/j.ddtec.2020.11.003Journal NLM ID: 101235076Publisher: Oxford: Elsevier
Correspondence: R. Adamo
Institutions: GSK, Via Fiorentina 1, 53100 Siena, Italy
- 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: 6318
Srtefanetti G, Maclennan CA, Micoli F "Impact and Control of Sugar Size in Glycoconjugate Vaccines" -
Molecules 27(19) (2022) 6432
Glycoconjugate vaccines have contributed enormously to reducing and controlling encapsulated bacterial infections for over thirty years. Glycoconjugate vaccines are based on a carbohydrate antigen that is covalently linked to a carrier protein; this is necessary to cause T cell responses for optimal immunogenicity, and to protect young children. Many interdependent parameters affect the immunogenicity of glycoconjugate vaccines, including the size of the saccharide antigen. Here, we examine and discuss the impact of glycan chain length on the efficacy of glycoconjugate vaccines and report the methods employed to size polysaccharide antigens, while highlighting the underlying reaction mechanisms. A better understanding of the impact of key parameters on the immunogenicity of glycoconjugates is critical to developing a new generation of highly effective vaccines.
glycoconjugates, vaccine, immunogenicity, fragmentation of polysaccharides, sugar length
NCBI PubMed ID: 36234967Publication DOI: 10.3390/molecules27196432Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: G. Srtefanetti
Institutions: Department of Biomolecular Sciences, University of Urbino Carlo Bo, 61029 Urbino, Italy, Enteric and Diarrheal Diseases, Global Health, Bill & Melinda Gates Foundation, 500 5th Ave. N, Seattle, WA 98109, USA, The Jenner Institute, Nuffield Department of Medicine, University of Oxford, Oxford OX3 7DQ, UK, The Institute of Immunology and Immunotherapy, University of Birmingham, Birmingham B15 2TT, UK, GSK Vaccines Institute for Global Health, 53100 Siena, Italy
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