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Structure type: polymer chemical repeating unit
Compound class: CPS, O-polysaccharide, O-antigen

• Article ID: 685
  Haseley SR, Holst O, Brade H "Structural and serological characterisation of the O-antigenic polysaccharide of the lipopolysaccharide from Acinetobacter haemolyticus strain ATCC17906" - European Journal of Biochemistry 244 (1997) 761-766
  

  A polysaccharide containing 2-acetamido-2-deoxy-D-galacturonic acid (GalNAcA), 2.4-diacetamido-2,4,6-trideoxy-D-glucose (QuiNAc4NAc), and D-alanine (Ala) was isolated from the water-soluble lipopolysaccharide (LPS) originating from the reference strain for Acinetobacter haemolyticus (DNA group 4) strain ATCC17906. The polysaccharide, characterised by means of monosaccharide analyses and NMR studies, was shown to be based on a linear trisaccharide repeating unit, as shown below, with the alanine group amide-bound to position 6 of one GalNAcA residue. It was specifically recognised in western blots by polyclonal rabbit antisera. [structure: see text]

  Lipopolysaccharide, LPS, strain, polysaccharide, O-antigenic, O-antigenic polysaccharide, Acinetobacter, Acinetobacter haemolyticus, Alanine, structura

  NCBI PubMed ID: 9108245
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: Division of Biochemical Microbiology, Research Centre Borstel, Germany.
  Methods: NMR-2D, NMR, Western blotting, methanolysis
  
   
  
  Acinetobacter haemolyticus ATCC 17906
  CSDB ID 488 (all data & tools)
• 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_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Acinetobacter haemolyticus ATCC 17906
  CSDB ID 27757 (all data & tools)
• Article ID: 5157
  Goyette-Desjardins G, Vinogradov E, Okura M, Takamatsu D, Gottschalk M, Segura M "Streptococcus suis serotype 3 and serotype 18 capsular polysaccharides contain di-N-acetyl-bacillosamine" - Carbohydrate Research 466 (2018) 18-29
  

  Streptococcus suis serotype 3 is counted among the S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 3 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence for serotype 3: [4)D-GlcA (β1-3)d-QuiNAc4NAc(β1-]n. To the best of our knowledge, this is the first report of di-N-acetyl-d-bacillosamine (QuiNAc4NAc) containing polysaccharides in Streptococci and the second time this rare diamino sugar has been observed in a Gram-positive bacterial species since its initial report. This led to the identification of homologues of UDP-QuiNAc4NAc synthesis genes in S. suis serotype 18. Thus, the repeating unit sequence for serotype 18 is: [3)d-GalNAc(α1-3)[d-Glc (β1-2)]d-GalA4OAc(β1-3)d-GalNAc(α1-3)d-QuiNAc4NAc(α1-]n. A correlation between S. suis serotypes 3 and 18 CPS sequences and genes of these serotypes' cps loci encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotypes 3 and 18.

  polysaccharide, capsular polysaccharide, polysaccharides, carbohydrate structure, Streptococcus suis, Di-N-Acetyl-bacillosamine, Serotype 18, Serotype 3

  NCBI PubMed ID: 30014879
  Publication DOI: 10.1016/j.carres.2018.07.003
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: mariela.segura@umontreal.ca
  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, periodate oxidation, gel filtration, NMR-2D, GC-MS, de-O-acylation, sugar analysis, methanolysis, SEC-MALS, bioinformatic analysis
  
   
  
  Acinetobacter haemolyticus ATCC 17906
  CSDB ID 12587 (all data & tools)
• Article ID: 5789
  Kenyon JJ, Senchenkova SN, Shashkov AS, Shneider MM, Popova AV, Knirel YA, Hall RM "K17 capsular polysaccharide produced by Acinetobacter baumannii isolate G7 contains an amide of 2-acetamido-2-deoxy-D-galacturonic acid with D-alanine" - International Journal of Biological Macromolecules 144 (2020) 857-862
  

  The K17 capsular polysaccharide (CPS) produced by Acinetobacter baumannii G7, which carries the KL17 configuration at the capsule biosynthesis locus, was isolated and studied by chemical methods along with one- and two-dimensional 1H and 13C NMR spectroscopy. Selective cleavage of the glycosidic linkage of a 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc) residue by (i) trifluoroacetic acid solvolysis or (ii) alkaline β-elimination (NaOH-NaBH4) of the 4-linked D-alanine amide of a 2-acetamido-2-deoxy-D-galacturonic acid residue (d-GalNAcA6DAla) yielded trisaccharides that were isolated by Fractogel TSK HW-40 gel-permeation chromatography and identified by using NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. The following structure was established for the trisaccharide repeat (K unit) of the CPS: →4)-α-D-GalpNAcA6DAla-(1→4)-α-D-GalpNAcA-(1→3)-β-D-QuipNAc4NAc-(1→. The presence of the itrA1 gene coding for the initial glycosylphosphotransferase in the KL17 gene cluster established the first sugar of the K unit as D-QuipNAc4NAc. KL17 includes genes for three transferases that had been annotated previously as glycosyltransferases (Gtrs). As only two Gtrs are required for the K17 structure and one D-GalpNAcA residue is modified by a D-alanine amide, these assignments were re-assessed. One transferase was found to belong to the ATPgrasp_TupA protein family that includes D-alanine-D-alanine ligases, and thus was renamed Alt1 (alanine transferase). Alt1 represents a novel family that amidate the carboxyl group of D-GalpNAcA or D-GalpA.

  Acinetobacter baumannii, capsular polysaccharide, D-alanine, K locus, KL17

  NCBI PubMed ID: 31715229
  Publication DOI: 10.1016/j.ijbiomac.2019.09.163
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: johanna.kenyon@qut.edu.au
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
  Methods: 13C NMR, NMR-2D, GLC, chemical methods, NMR-1D, GPC, bioinformatic analysis, solvolysis with trifluoroacetic acid, HR-ESI-MS1H NMR
  
   
  
  Acinetobacter baumannii K17 G7
  CSDB ID 32130 (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
  
   
  
  Acinetobacter baumannii K17 G7
  CSDB ID 6732 (all data & tools)
• Article ID: 6411
  Kasimova AA, Sharar NS, Ambrose SJ, Knirel YA, Shneider MM, Timoshina OY, Popova AV, Perepelov AV, Dmitrenok AS, Hsu LY, Hall RM, Kenyon JJ "The Acinetobacter baumannii K70 and K9 capsular polysaccharides consist of related K-units linked by the same Wzy polymerase and cleaved by the same phage depolymerases" - Microbiology Spectrum 11(6) (2023) e0302523
  

  Bacteriophage show promise for the treatment of Acinetobacter baumannii infections that resist all therapeutically suitable antibiotics. Many tail-spike depolymerases encoded by phage that are able to degrade A. baumannii capsular polysaccharide (CPS) exhibit specificity for the linkage present between K-units that make up CPS polymers. This linkage is formed by a specific Wzy polymerase, and the ability to predict this linkage using sequence-based methods that identify the Wzy at the K locus could assist with the selection of phage for therapy. However, little is known about the specificity of Wzy polymerase enzymes. Here, we describe a Wzy polymerase that can accommodate two different but similar sugars as one of the residues it links and phage depolymerases that can cleave both types of bond that Wzy forms.

  Acinetobacter baumannii, capsular polysaccharide, Wzy polymerase, phage depolymerase, K70

  NCBI PubMed ID: 37975684
  Publication DOI: 10.1128/spectrum.03025-23
  Journal NLM ID: 101634614
  Publisher: Washington, DC: ASM Press
  Correspondence: J.J. Kenyon
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, M. M. Shemyakin and Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, Faculty of Science, University of Sydney, Sydney, Australia, Saw Swee Hock School of Public Health, National University of Singapore, Queenstown, Singapore, Yong Loo Lin School of Medicine, National University of Singapore, Queenstown, Singapore
  Methods: 13C NMR, 1H NMR, NMR-2D, DNA sequencing, sugar analysis, DNA techniques, GLC, Smith degradation, HPLC, GPC, bioinformatic analysis, phage depolymerisation, HR-ESI-MS
  
   
  
  Acinetobacter baumannii K17 G7
  CSDB ID 20750 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 750.2682 [M-H]-
C₂₉H₄₅N₅O₁₈
Compound class: CPS

• Article ID: 5789
  Kenyon JJ, Senchenkova SN, Shashkov AS, Shneider MM, Popova AV, Knirel YA, Hall RM "K17 capsular polysaccharide produced by Acinetobacter baumannii isolate G7 contains an amide of 2-acetamido-2-deoxy-D-galacturonic acid with D-alanine" - International Journal of Biological Macromolecules 144 (2020) 857-862
  

  The K17 capsular polysaccharide (CPS) produced by Acinetobacter baumannii G7, which carries the KL17 configuration at the capsule biosynthesis locus, was isolated and studied by chemical methods along with one- and two-dimensional 1H and 13C NMR spectroscopy. Selective cleavage of the glycosidic linkage of a 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc) residue by (i) trifluoroacetic acid solvolysis or (ii) alkaline β-elimination (NaOH-NaBH4) of the 4-linked D-alanine amide of a 2-acetamido-2-deoxy-D-galacturonic acid residue (d-GalNAcA6DAla) yielded trisaccharides that were isolated by Fractogel TSK HW-40 gel-permeation chromatography and identified by using NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. The following structure was established for the trisaccharide repeat (K unit) of the CPS: →4)-α-D-GalpNAcA6DAla-(1→4)-α-D-GalpNAcA-(1→3)-β-D-QuipNAc4NAc-(1→. The presence of the itrA1 gene coding for the initial glycosylphosphotransferase in the KL17 gene cluster established the first sugar of the K unit as D-QuipNAc4NAc. KL17 includes genes for three transferases that had been annotated previously as glycosyltransferases (Gtrs). As only two Gtrs are required for the K17 structure and one D-GalpNAcA residue is modified by a D-alanine amide, these assignments were re-assessed. One transferase was found to belong to the ATPgrasp_TupA protein family that includes D-alanine-D-alanine ligases, and thus was renamed Alt1 (alanine transferase). Alt1 represents a novel family that amidate the carboxyl group of D-GalpNAcA or D-GalpA.

  Acinetobacter baumannii, capsular polysaccharide, D-alanine, K locus, KL17

  NCBI PubMed ID: 31715229
  Publication DOI: 10.1016/j.ijbiomac.2019.09.163
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: johanna.kenyon@qut.edu.au
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
  Methods: 13C NMR, NMR-2D, GLC, chemical methods, NMR-1D, GPC, bioinformatic analysis, solvolysis with trifluoroacetic acid, HR-ESI-MS1H NMR
  
   
  
  Acinetobacter baumannii K17 G7
  CSDB ID 4189 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 734.2732 [M-H]-
C₂₉H₄₅N₅O₁₇
Compound class: CPS

• Article ID: 5789
  Kenyon JJ, Senchenkova SN, Shashkov AS, Shneider MM, Popova AV, Knirel YA, Hall RM "K17 capsular polysaccharide produced by Acinetobacter baumannii isolate G7 contains an amide of 2-acetamido-2-deoxy-D-galacturonic acid with D-alanine" - International Journal of Biological Macromolecules 144 (2020) 857-862
  

  The K17 capsular polysaccharide (CPS) produced by Acinetobacter baumannii G7, which carries the KL17 configuration at the capsule biosynthesis locus, was isolated and studied by chemical methods along with one- and two-dimensional 1H and 13C NMR spectroscopy. Selective cleavage of the glycosidic linkage of a 2,4-diacetamido-2,4,6-trideoxy-D-glucose (D-QuiNAc4NAc) residue by (i) trifluoroacetic acid solvolysis or (ii) alkaline β-elimination (NaOH-NaBH4) of the 4-linked D-alanine amide of a 2-acetamido-2-deoxy-D-galacturonic acid residue (d-GalNAcA6DAla) yielded trisaccharides that were isolated by Fractogel TSK HW-40 gel-permeation chromatography and identified by using NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. The following structure was established for the trisaccharide repeat (K unit) of the CPS: →4)-α-D-GalpNAcA6DAla-(1→4)-α-D-GalpNAcA-(1→3)-β-D-QuipNAc4NAc-(1→. The presence of the itrA1 gene coding for the initial glycosylphosphotransferase in the KL17 gene cluster established the first sugar of the K unit as D-QuipNAc4NAc. KL17 includes genes for three transferases that had been annotated previously as glycosyltransferases (Gtrs). As only two Gtrs are required for the K17 structure and one D-GalpNAcA residue is modified by a D-alanine amide, these assignments were re-assessed. One transferase was found to belong to the ATPgrasp_TupA protein family that includes D-alanine-D-alanine ligases, and thus was renamed Alt1 (alanine transferase). Alt1 represents a novel family that amidate the carboxyl group of D-GalpNAcA or D-GalpA.

  Acinetobacter baumannii, capsular polysaccharide, D-alanine, K locus, KL17

  NCBI PubMed ID: 31715229
  Publication DOI: 10.1016/j.ijbiomac.2019.09.163
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: johanna.kenyon@qut.edu.au
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, M. M. Shemyakin & Y. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, Moscow Region, Russia, Moscow Institute of Physics and Technology, Dolgoprudny, Moscow Region, Russia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Antimicrobial Chemotherapy, Smolensk State Medical University, Smolensk, Russia
  Methods: 13C NMR, NMR-2D, GLC, chemical methods, NMR-1D, GPC, bioinformatic analysis, solvolysis with trifluoroacetic acid, HR-ESI-MS1H NMR
  
   
  
  Acinetobacter baumannii K17 G7
  CSDB ID 4190 (all data & tools)