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Structure type: polymer chemical repeating unit
Trivial name: K11 CPS
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 5008
  Kenyon JJ, Shashkov AS, Senchenkova SN, Shneider MM, Liu B, Popova AV, Arbatsky NP, Miroshnikov KA, Wang L, Knirel YA, Hall RM "Acinetobacter baumannii K11 and K83 capsular polysaccharides have the same 6-deoxy-L-talose-containing pentasaccharide K units but different linkages between the K units" - International Journal of Biological Macromolecules 103 (2017) 648-655
  

  Acinetobacter baumannii produces a variety of capsular polysaccharides (CPS) via genes located at the chromosomal K locus and some KL gene clusters include genes for the synthesis of specific sugars. The structures of K11 and K83 CPS produced by isolates LUH5545 and LUH5538, which carry related KL11a and KL83 gene clusters, respectively, were established by sugar analysis and one- and two-dimensional 1H and 13C NMR spectroscopy. Both CPS contain l-rhamnose (l-Rha) and 6-deoxy-l-talose (l-6dTal), and both KL gene clusters include genes for dTDP-l-Rhap synthesis and a tle (talose epimerase) gene encoding an epimerase that converts dTDP-l-Rhap to dTDP-l-6dTalp. The K11 and K83 repeat units are the same pentasaccharide, consisting of d-glucose, l-Rha, l-6dTal, and N-acetyl-d-glucosamine, except that l-6dTal is 2-O-acetylated in K83. However, the K units are linked differently, with l-Rha in the main chain in K11, but as a side-branch in K83. KL11 and KL83 encode unrelated Wzy polymerases that link the K units together and different acetyltransferases, though only Atr8 from KL83 is active. The substrate specificity of each Wzy polymerase was assigned, and the functions of all glycosyltransferases were predicted. The CPS structures produced by three closely related K loci, KL29, KL105 and KL106, were also predicted.

  Acinetobacter baumannii, capsular polysaccharide, 6-deoxy-L-talose

  NCBI PubMed ID: 28528003
  Publication DOI: 10.1016/j.ijbiomac.2017.05.082
  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, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Institute of Health and Biomedical Innovation, School of Biomedical Sciences, Queensland University of Technology, Brisbane, Australia, TEDA Institute of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, PR China
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, GLC, Smith degradation, de-O-acetylation, GPC, bioinformatic analysis
  
   
  
  Acinetobacter baumannii LUH5545 (G4777)
  CSDB ID 12116 (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 K11a LUH5545
  CSDB ID 6754 (all data & tools)
• Article ID: 6077
  Kasimova AA, Arbatsky NP, Tickner J, Kenyon JJ, Hall RM, Shneider MM, Dzhaparova AA, Shashkov AS, Chizhov AO, Popova AV, Knirel YA "Acinetobacter baumannii K106 and K112: Two Structurally and Genetically Related 6-Deoxy-l-talose-Containing Capsular Polysaccharides" - International Journal of Molecular Sciences 22(11) (2021) 5641
  

  Whole genome sequences of two Acinetobacter baumannii clinical isolates, 48-1789 and MAR24, revealed that they carry the KL106 and KL112 capsular polysaccharide (CPS) biosynthesis gene clusters, respectively, at the chromosomal K locus. The KL106 and KL112 gene clusters are related to the previously described KL11 and KL83 gene clusters, sharing genes for the synthesis of l-rhamnose (l-Rhap) and 6-deoxy-l-talose (l-6dTalp). CPS material isolated from 48-1789 and MAR24 was studied by sugar analysis and Smith degradation along with one- and two-dimensional 1H and 13C NMR spectroscopy. The structures of K106 and K112 oligosaccharide repeats (K units) l-6dTalp-(1→3)-D-GlcpNAc tetrasaccharide fragment share the responsible genes in the respective gene clusters. The K106 and K83 CPSs also have the same linkage between K units. The KL112 cluster includes an additional glycosyltransferase gene, Gtr183, and the K112 unit includes α l-Rhap side chain that is not found in the K106 structure. K112 further differs in the linkage between K units formed by the Wzy polymerase, and a different wzy gene is found in KL112. However, though both KL106 and KL112 share the atr8 acetyltransferase gene with KL83, only K83 is acetylated.

  Acinetobacter baumannii, capsular polysaccharide, 6-deoxy-L-talose, K locus, K106, K112

  NCBI PubMed ID: 34073255
  Publication DOI: 10.3390/ijms22115641
  Journal NLM ID: 101092791
  Publisher: Basel, Switzerland: MDPI
  Correspondence: A.O. Chizhov
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, School of Life and Environmental Sciences, The University of Sydney, Sydney, NSW 2006, Australia, Centre for Immunology and Infection Control, School of Biomedical Sciences, Faculty of Health, Queensland University of Technology, Brisbane, QLD 4059, Australia, M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 117997 Moscow, Russia, State Research Center for Applied Microbiology and Biotechnology, Obolensk, 142279 Moscow Region, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, GLC, Smith degradation, composition analysis, GPC, bioinformatic analysis, HR-ESI-MS, sequencing
  
   
  
  Acinetobacter baumannii K11
  CSDB ID 10873 (all data & tools)
• Article ID: 6079
  Kasimova AA, Arbatsky NP, Timoshina OY, Shneider MM, Shashkov AS, Chizhov AO, Popova AV, Hall RM, Kenyon JJ, Knirel YA "The K26 capsular polysaccharide from Acinetobacter baumannii KZ-1098: Structure and cleavage by a specific phage depolymerase" - International Journal of Biological Macromolecules 191 (2021) 182-191
  

  The KL26 gene cluster responsible for the synthesis of the K26 capsular polysaccharide (CPS) of Acinetobacter baumannii includes rmlBDAC genes for l-rhamnose (l-Rhap) synthesis, tle to generate 6-deoxy-l-talose (l-6dTalp) from l-Rhap, and a manC gene for D-mannose (D-Manp) that is rare in Acinetobacter CPS. K26 CPS material was isolated from A. baumannii isolate KZ-1098, and studied by sugar analysis, Smith degradation, and one and two-dimensional 1H and 13C NMR spectroscopy before and after O-deacetylation with aqueous ammonia. The following structure of the branched hexasaccharide repeating unit of the CPS was established: →2)-β-D-Manp-1→4-β-D-Glcp-1→3-α-L-6dTalp-1→3-β-D-GlcpNAc-(1→3↑14│Acα-L-Rhap-2←1-α-D-Glcp The structural depolymerase of phage vB_AbaP_APK26 cleaved selectively the β-GlcpNAc-(1→2)-α-Manp linkage in the K26 CPS formed by WzyK26 to give monomer, dimer, and trimer of the CPS repeating unit, which were characterized by high-resolution electrospray ionization mass spectrometry as well as 1H and 13C NMR spectroscopy. The wzyK26 gene responsible for this linkage and the manC gene were only found in six A. baumannii genomes carrying KL26 and one carrying the novel KL148 gene cluster, indicating the rare occurrence of β-GlcpNAc-(1→2)-α-Manp in A. baumannii CPS structures. However, K26 shares a β-d-Glcp-(1→3)-α-l-6dTalp-(1→3)-β-d-GlcpNAc trisaccharide fragment with a group of related A. baumannii CPSs that have varying patterns of acetylation of l-6dTalp.

  Acinetobacter baumannii, capsular polysaccharide structure, 6-deoxy-L-talose, depolymerization, A.baumannii, phage depolymerase

  NCBI PubMed ID: 34537298
  Publication DOI: 10.1016/j.ijbiomac.2021.09.073
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: J.J. Kenyon
  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, 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
  Methods: 13C NMR, 1H NMR, NMR-2D, PCR, sugar analysis, GLC, Smith degradation, de-O-acetylation, HPLC, GPC, bioinformatic analysis, HR-ESI-MS, sequencing, phage characterization, depolymerization by phage
  
   
  
  Acinetobacter baumannii K11
  CSDB ID 5854 (all data & tools)
• Article ID: 6167
  Yakovleva L, Fulleborn JA, Walvoort MTC "Opportunities and Challenges of Bacterial Glycosylation for the Development of Novel Antibacterial Strategies" - Frontiers in Microbiology 12 (2021) 745702
  

  Glycosylation is a ubiquitous process that is universally conserved in nature. The various products of glycosylation, such as polysaccharides, glycoproteins, and glycolipids, perform a myriad of intra- and extracellular functions. The multitude of roles performed by these molecules is reflected in the significant diversity of glycan structures and linkages found in eukaryotes and prokaryotes. Importantly, glycosylation is highly relevant for the virulence of many bacterial pathogens. Various surface-associated glycoconjugates have been identified in bacteria that promote infectious behavior and survival in the host through motility, adhesion, molecular mimicry, and immune system manipulation. Interestingly, bacterial glycosylation systems that produce these virulence factors frequently feature rare monosaccharides and unusual glycosylation mechanisms. Owing to their marked difference from human glycosylation, bacterial glycosylation systems constitute promising antibacterial targets. With the rise of antibiotic resistance and depletion of the antibiotic pipeline, novel drug targets are urgently needed. Bacteria-specific glycosylation systems are especially promising for antivirulence therapies that do not eliminate a bacterial population, but rather alleviate its pathogenesis. In this review, we describe a selection of unique glycosylation systems in bacterial pathogens and their role in bacterial homeostasis and infection, with a focus on virulence factors. In addition, recent advances to inhibit the enzymes involved in these glycosylation systems and target the bacterial glycan structures directly will be highlighted. Together, this review provides an overview of the current status and promise for the future of using bacterial glycosylation to develop novel antibacterial strategies.

  glycosylation, pathogenic bacteria, metabolic oligosaccharide engineering, antibacterial strategies, antivirulence

  NCBI PubMed ID: 34630370
  Publication DOI: 10.3389/fmicb.2021.745702
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: Marthe T.C. Walvoort
  Institutions: Faculty of Science and Engineering, Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands
  
   
  
  Acinetobacter baumannii K11
  CSDB ID 10419 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 983.3759 [M-H]-
C₄₁H₆₃N₂O₂₅
Aglycon: p-methoxyphenyl
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 6365
  Bharali MM, Santa A "Total Synthesis of 6-Deoxy-l-talose Containing a Pentasaccharide Repeating Unit of Acinetobacter baumannii K11 Capsular Polysaccharides" - Journal of Organic Chemistry 88(13) (2023) 8770-8780
  

  Herein, we report a concise synthetic approach for the first total synthesis of a pentasaccharide repeating unit of Acinetobacter baumannii K11 capsular polysaccharides containing a rare sugar 6-deoxy-l-talose. The pentasaccharide was synthesized in a convergent manner using a [3 + 2] block glycosylation strategy. During this synthetic strive, we used a 2,2,2-trichloroethoxycarbonyl (Troc)-protected monosaccharide unit to achieve a high yield during the glycosylation to synthesize a trisaccharide, and chemoselective deprotection of the Troc group from the trisaccharide was carried out under a mild, pH-neutral condition, keeping the O-glycosidic bond, azido, and acid/base sensitive group intact. A thiotolylglycoside disaccharide donor containing 6-deoxy-l-talose was synthesized for the first time by the armed-disarmed glycosylation method between two thiotolylglycosides.

  repeating unit, Acinetobacter baumannii, capsular polysaccharide, 6-deoxy-L-talose, glycosylation, total synthesis

  NCBI PubMed ID: 37340701
  Publication DOI: 10.1021/acs.joc.3c00615
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Correspondence: A. Santa
  Institutions: Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India, Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, glycosylation, optical rotation measurement, CC, HR-ESI-MS, DEPT-135
  
   
  
  Acinetobacter baumannii K11
  CSDB ID 22210 (all data & tools)