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Structure type: polymer chemical repeating unit
Compound class: CPS

• Article ID: 4795
  Senchenkova SN, Shashkov AS, Popova AV, Shneider MM, Arbatsky NP, Miroshnikov KA, Volozhantsev NV, Knirel YA "Structure elucidation of the capsular polysaccharide of Acinetobacter baumannii AB5075 having the KL25 capsule biosynthesis locus" - Carbohydrate Research 408 (2015) 8-11
  

  Capsular polysaccharide was isolated by the phenol-water extraction of Acinetobacter baumannii AB5075 and studied by 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear trisaccharide repeating unit was established: →3)-β-D-ManpNAcA-(1→4)-β-D-ManpNAcA-(1→3)-α-D-QuipNAc4NR-(1→ where R indicates (S)-3-hydroxybutanoyl or acetyl in the ratio ∼ 2.5:1. The genes in the polysaccharide biosynthesis locus designated KL25 are appropriate to the established CPS structure.

  Acinetobacter baumannii, capsular polysaccharide structure, polysaccharide gene locus

  NCBI PubMed ID: 25816997
  Publication DOI: 10.1016/j.carres.2015.02.011
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: yknirel@gmail.com
  Institutions: 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, ND. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, NMR-1D, GPC, bioinformatic analysis
  
   
  
  Acinetobacter baumannii AB5075 (MRSN959)
  CSDB ID 30670 (all data & tools)
• 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: 26531136
  Publication DOI: 10.1016/j.carres.2015.10.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: denis.giguere@chm.ulaval.ca
  Institutions: Département de Chimie, Université Laval, Québec City, Québec, Canada G1V 0A6
  
   
  
  Acinetobacter baumannii AB5075
  CSDB ID 30946 (all data & tools)
• Article ID: 6177
  Zhang S, Seeberger PH "Total Syntheses of Conjugation-Ready Repeating Units of Acinetobacter baumannii AB5075 for Glycoconjugate Vaccine Development" - Chemistry: a European Journal 27(69) (2021) 17444-17451
  

  Acinetobacter baumannii is an opportunistic pathogen that causes serious nosocomial infections. One of the multidrug-resistant strains, AB5075, can result in bacteremia, pneumonia and wound infections associated with high morbidity and mortality. The structurally unique glycans on the surface of these bacteria are attractive targets for the development of glycoconjugate vaccines. Here, we report the first total synthesis of the densely functionalized trisaccharide repeating unit of A. baumannii AB5075 as well as two analogues. The construction of 1,2-cis linkages between the rare sugars relies on a double-serial inversion strategy. The judicious selection of building blocks and reaction conditions allowed for stereoselective glycosylations, the installation of acetamido groups and the (S)-3-hydroxybutanoyl chain.

  carbohydrates, Acinetobacter baumannii, Oligosaccharides, vaccines, Amides, total synthesis

  NCBI PubMed ID: 34665908
  Publication DOI: 10.1002/chem.202103234
  Journal NLM ID: 9513783
  Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
  Correspondence: Peter.Seeberger@mpikg.mpg.de
  Institutions: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476, Potsdam, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, FTIR, glycosylation
  
   
  
  Acinetobacter baumannii K25 AB5075
  CSDB ID 10980 (all data & tools)

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Structure type: polymer chemical repeating unit
Compound class: CPS

• 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 K25 AB5075
  CSDB ID 6735 (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 K25 AB5075
  CSDB ID 20752 (all data & tools)

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Structure type: oligomer
Aglycon: (1->1) 5-aminopentyl
Compound class: CPS

• Article ID: 6177
  Zhang S, Seeberger PH "Total Syntheses of Conjugation-Ready Repeating Units of Acinetobacter baumannii AB5075 for Glycoconjugate Vaccine Development" - Chemistry: a European Journal 27(69) (2021) 17444-17451
  

  Acinetobacter baumannii is an opportunistic pathogen that causes serious nosocomial infections. One of the multidrug-resistant strains, AB5075, can result in bacteremia, pneumonia and wound infections associated with high morbidity and mortality. The structurally unique glycans on the surface of these bacteria are attractive targets for the development of glycoconjugate vaccines. Here, we report the first total synthesis of the densely functionalized trisaccharide repeating unit of A. baumannii AB5075 as well as two analogues. The construction of 1,2-cis linkages between the rare sugars relies on a double-serial inversion strategy. The judicious selection of building blocks and reaction conditions allowed for stereoselective glycosylations, the installation of acetamido groups and the (S)-3-hydroxybutanoyl chain.

  carbohydrates, Acinetobacter baumannii, Oligosaccharides, vaccines, Amides, total synthesis

  NCBI PubMed ID: 34665908
  Publication DOI: 10.1002/chem.202103234
  Journal NLM ID: 9513783
  Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
  Correspondence: Peter.Seeberger@mpikg.mpg.de
  Institutions: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476, Potsdam, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, FTIR, glycosylation
  
   
  
  Acinetobacter baumannii K25 AB5075
  CSDB ID 10448 (all data & tools)