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Structure type: monomer

• Article ID: 125
  Tsvetkov YE, Shashkov AS, Knirel YA, Zähringer U "Synthesis and NMR spectroscopy of nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids" - Carbohydrate Research 335(4) (2001) 221-243
  

  Derivatives of 5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids are essential constituents of some bacterial polysaccharides and glycoproteins. In order to establish reliably the configuration of the natural sugars, nine stereoisomeric 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acids were synthesized, including di-N-acetyl-legionaminic and -pseudaminic acids (the D-glycero-D-galacto and L-glycero-L-manno isomers, respectively) and their isomers at C-4, C-5, C-7, and C-8 having the L-glycero-D-galacto, D-glycero-D-talo, L-glycero-D-talo, D-glycero-L-altro, L-glycero-L-altro, D-glycero-L-manno, and L-glycero-L-gluco configurations. Synthesis was performed by condensation of 2,4-diacetamido-2,4,6-trideoxy-L-gulose, -D-mannose, -D-talose, and -L-allose with oxalacetic acid under basic conditions, the reaction of the last two precursors being accompanied by epimerisation at C-2. The 1H and 13C NMR data of the synthetic compounds are discussed. Acetylated methyl esters of the C-7 and C-8 isomeric nonulosonic acids were prepared and used for analysis of the side-chain conformation by NMR spectroscopy.

  NMR, synthesis, LPS, Bacterial, identification, acid, NMR spectroscopy, pseudaminic acid, putative, spectroscopy, 5, 7-diamino-3, 7, 9-tetradeoxynon-2-ulosonic acid, lipopolysaccharide components, 7-diacetamido-3, 9-tetradeoxynon-2-ulosonic acids, 2, 4-diacetamido-2, 4, 6-trideoxyhexoses, legionaminic acid, 9-teradeoxynonulosonic acid, component, isomer

  NCBI PubMed ID: 11595217
  Publication DOI: 10.1016/S0008-6215(01)00235-X
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: tsvetkov@ioc.ac.ru
  Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospeckt 47, Moscow, Russian Federation, Forschungszentrum Borstel, Zentrum fur Medizin und Biowissenschaften, Borstel, Germany.
  Methods: 13C NMR, 1H NMR
  
   
  
  (bacteria)
  CSDB ID 5353 (all data & tools)

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Structure type: monomer
Compound class: CPS

• Article ID: 5007
  Kenyon JJ, Notaro A, Hsu LY, De Castro C, Hall RM "5,7-Di-N-acetyl-8-epiacinetaminic acid: A new non-2-ulosonic acid found in the K73 capsule produced by an Acinetobacter baumannii isolate from Singapore" - Scientific Reports 7(1) (2017) 11357
  

  Nonulosonic acids are found in the surface polysaccharides of many bacterial species and are often implicated in pathogenesis. Here, the structure of a novel 5,7-diacetamido-3,5,7,9-tetradeoxynon-2-ulosonic acid recovered from the capsular polysaccharide of a multiply antibiotic resistant Acinetobacter baumannii isolate was determined. The isolate carries a sugar synthesis module that differs by only a single gene from the module for the synthesis of 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-altro-non-2-ulosonic acid or 5,7-di-N-acetylacinetaminic acid, recently discovered in the capsule of another A. baumannii isolate. The new monosaccharide is the C8-epimer of acinetaminic acid (8eAci; 5,7-diacetamido-3,5,7,9-tetradeoxy-D-glycero-L-altro-non-2-ulosonic acid) and the C7-epimer of legionaminic acid. This monosaccharide had not previously been detected in a biological sample but had been synthesized chemically.

  structure, capsular polysaccharide, Acinetobacter baumannii, nonulosonic acid, 5, 7, 7-diacetamido-3, legionaminic acid, capsule, surface polysaccharide, 7-Di-N-acetyl-8-epiacinetaminic acid, 9-tetradeoxy-D-glycero-L-altro-non-2-ulosonic acid

  NCBI PubMed ID: 28900250
  Publication DOI: 10.1038/s41598-017-11166-4
  Journal NLM ID: 101563288
  Publisher: London: Nature Publishing Group
  Correspondence: decastro@unina.it; ruth.hall@sydney.edu.au
  Institutions: Institute of Health and Biomedical Innovation, Queensland University of Technology, Brisbane, Australia, School of Life and Environmental Sciences, The University of Sydney, Sydney, Australia, Department of Chemical Sciences, University of Napoli, Naples, Italy, Saw Swee Hock School of Public Health, National University of Singapore, Singapore, Singapore, Department of Infectious Diseases, Tan Tock Seng Hospital, Singapore, Singapore, Department of Agricultural Sciences, University of Napoli, Naples, Italy
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, DNA sequencing, GC-MS, enzymatic hydrolysis, mild acid hydrolysis, composition analysis, bioinformatic analysis, SEC
  
   
  
  Acinetobacter baumannii SGH 0703 (DB24441)
  CSDB ID 12115 (all data & tools)