Found 3 structures.
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1. Compound ID: 2076
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b-D-ManpNAc-(1-4)-a-D-Galp-(1-4)-+
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-3)-b-D-GalpNAc-(1-3)-b-D-Galp-(1- |
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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144987,IEDB_147450,IEDB_151528,IEDB_190606,IEDB_742247,IEDB_885813,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_31,SB_62,SB_7,SB_8,SB_88
The structure is contained in the following publication(s):
- Article ID: 680
Haseley S, Wilkinson SG "Structure of the O18 antigen from Acinetobacter baumannii" -
Carbohydrate Research 301(3-4) (1997) 187-192
The polymeric O antigen was obtained from lipopolysaccharide extracted from isolated, defatted cell walls of the reference strain for Acinetobacter baumannii serogroup O18. Monosaccharide analyses and NMR spectra established that the polymer had a regular structure with a repeating unit based on residues of D-galactose (2), N-acetyl-D-galactosamine (1), and N-acetyl-D-mannosamine (1). Further interpretation of the NMR spectra, combined with the results of methylation analysis and a Smith degradation, showed that the repeating unit had the following structure. β-D-ManpNAc-(1→4)-α-D-Galp 1 decreases 4 →3)-β-D-GalpNAc-(1→3)-β-D-Galp-(1→.
Lipopolysaccharide, antigen, LPS, structure, Acinetobacter, Acinetobacter baumannii, O18 antigen
NCBI PubMed ID: 9232839Journal NLM ID: 0043535Publisher: Elsevier
Institutions: School of Chemistry, University of Hull, UK.
Methods: methylation, NMR, Smith degradation
- Article ID: 4329
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
- Article ID: 4534
Hu D, Liu B, Dijkshoorn L, Wang L, Reeves PR "Diversity in the major polysaccharide antigen of Acinetobacter baumannii assessed by DNA sequencing, and development of a molecular serotyping scheme" -
PLoS One 8(7) (2013) e70329
We have sequenced the gene clusters for type strains of the Acinetobacter baumannii serotyping scheme developed in the 1990s, and used the sequences to better understand diversity in surface polysaccharides of the genus. We obtained genome sequences for 27 available serovar type strains, and identified 25 polysaccharide gene cluster sequences. There are structures for 12 of these polysaccharides, and in general the genes present are appropriate to the structure where known. This greatly facilitates interpretation. We also find 53 different glycosyltransferase genes, and for 7 strains can provisionally allocate specific genes to all linkages. We identified primers that will distinguish the 25 sequence forms by PCR or microarray, or alternatively the genes can be used to determine serotype by 'molecular serology'. We applied the latter to 190 Acinetobacter genome-derived gene-clusters, and found 76 that have one of the 25 gene-cluster forms. We also found novel gene clusters and added 52 new gene-cluster sequence forms with different wzy genes and different gene contents. Altogether, the strains that have one of the original 25 sequence forms include 98 A. baumannii (24 from our strains) and 5 A. nosocomialis (3 from our strains), whereas 32 genomes from 12 species other than A. baumannii or A. nosocomialis, all have new sequence forms. One of the 25 serovar type sequences is found to be in European clone I (EC I), 2 are in EC II but none in EC III. The public genome strains add an additional 52 new sequence forms, and also bring the number found in EC I to 5, in EC II to 9 and in EC III to 2.
antigen, structure, Acinetobacter baumannii, gene cluster, glycosyltransferase, serotyping, genome, surface polysaccharide, polysaccharide antigen
NCBI PubMed ID: 23922982Publication DOI: 10.1371/journal.pone.0070329Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Peter R. Reeves
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China, Department of Infectious Diseases, Leiden University Medical Center, Leiden, The Netherlands, School of Molecular Bioscience, University of Sydney, Sydney, Australia
Methods: PCR, DNA sequencing, DNA techniques, genetic methods
- Article ID: 4750
Arihara R, Kakita K, Yamada K, Nakamura S, Hashimoto S "Synthesis of the Tetrasaccharide Repeating Unit from Acinetobacter baumannii Serogroup O18 Capitalizing on Phosphorus-containing Leaving Groups" -
Journal of Organic Chemistry 80(9) (2015) 4278-4288
The first convergent synthesis of the tetrasaccharide repeating unit of the polymeric O antigen isolated from Acinetobacter baumannii serogroup O18 has been achieved. The ManNAc β1→4 Gal and GalNAc β1→3 Gal units were successfully obtained through beta-selective glycosylation with 2- azido-4,6-O-benzylidene-2-deoxymannosyl diphenyl phosphate and Tf2NH-promoted glycosylation with 2-acetamido-2-deoxygalactosyl diethyl phosphite, respectively. The disaccharide units could be coupled with the aid of TMSClO4 as an activator of the diphenyl phosphate leaving group, and global deprotection completed the synthesis of the tetrasaccharide.
O-antigen, Acinetobacter baumannii
NCBI PubMed ID: 25807254Publication DOI: 10.1021/acs.joc.5b00139Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: nakamura@phar.nagoya-cu.ac.jp; hsmt@pharm.hokudai.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, chemical methods, MS, glycosylation
- Article ID: 4819
Giguere D "Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses" -
Carbohydrate Research 418 (2015) 29-43
The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.
lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides
NCBI PubMed ID: 26531136Publication DOI: 10.1016/j.carres.2015.10.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: denis.giguere@chm.ulaval.ca
Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
- 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
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2. Compound ID: 11902
Structure type: oligomer
; 749.28 [M+H]+
C28H49N2O21
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144987,IEDB_151528,IEDB_190606,IEDB_742247,IEDB_885813,SB_165,SB_166,SB_187,SB_195,SB_21,SB_31,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4750
Arihara R, Kakita K, Yamada K, Nakamura S, Hashimoto S "Synthesis of the Tetrasaccharide Repeating Unit from Acinetobacter baumannii Serogroup O18 Capitalizing on Phosphorus-containing Leaving Groups" -
Journal of Organic Chemistry 80(9) (2015) 4278-4288
The first convergent synthesis of the tetrasaccharide repeating unit of the polymeric O antigen isolated from Acinetobacter baumannii serogroup O18 has been achieved. The ManNAc β1→4 Gal and GalNAc β1→3 Gal units were successfully obtained through beta-selective glycosylation with 2- azido-4,6-O-benzylidene-2-deoxymannosyl diphenyl phosphate and Tf2NH-promoted glycosylation with 2-acetamido-2-deoxygalactosyl diethyl phosphite, respectively. The disaccharide units could be coupled with the aid of TMSClO4 as an activator of the diphenyl phosphate leaving group, and global deprotection completed the synthesis of the tetrasaccharide.
O-antigen, Acinetobacter baumannii
NCBI PubMed ID: 25807254Publication DOI: 10.1021/acs.joc.5b00139Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: nakamura@phar.nagoya-cu.ac.jp; hsmt@pharm.hokudai.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, chemical methods, MS, glycosylation
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3. Compound ID: 12080
Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144987,IEDB_151528,IEDB_190606,IEDB_742247,IEDB_885813,SB_165,SB_166,SB_187,SB_195,SB_21,SB_31,SB_62,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 4819
Giguere D "Surface polysaccharides from Acinetobacter baumannii: Structures and syntheses" -
Carbohydrate Research 418 (2015) 29-43
The emergence of multidrug-resistance Acinetobacter baumannii requires novel approaches for prevention, treatment and diagnosis. The structures of surface polysaccharides from A. baumannii are valuable tools to understand pathogenesis, virulence and immunogenicity. The synthesis of bacterial mono- or polysaccharides may result in novel probes to become important therapeutic options in the fight against A. baumannii. This report exemplifies the relevance of glycochemistry for the development of new antibiotics.
lipopolysaccharides, capsular polysaccharides, Acinetobacter, Acinetobacter baumannii, polysaccharide synthesis, surface polysaccharides
NCBI PubMed ID: 26531136Publication DOI: 10.1016/j.carres.2015.10.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: denis.giguere@chm.ulaval.ca
Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
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