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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_130701,IEDB_137473,IEDB_141793,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_983930,SB_198,SB_44,SB_67,SB_72

• Article ID: 4406
  Tomshich SV, Isakov VV, Komandrova NA, Shevchenko LS "Structure of the O-Specific Polysaccharide of the Marine Bacterium Arenibacter palladensis KMM 3961(T) Containing 2-Acetamido-2-deoxy-L-galacturonic Acid" - Biochemistry (Moscow) 77(1) (2012) 87-91
  

  The O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of the marine bacterium Arenibacter palladensis type strain KMM 3961(T) and studied by chemical methods and (1)H and (13)C NMR spectroscopy including 2D COSY, TOCSY, (1)H,(13)C HSQC, and HMBC experiments. The polysaccharide was shown to consist of tetrasaccharide repeating units containing two mannose residues (Man), one 2-acetamido-2-deoxy-D-galactose residue (D-GalNAc), and one 2-acetamido-2-deoxy-L-galacturonic acid residue (L-GalNAcA) and having the following structure: →2)-α-D-Manp-(1→6)-α-D-Manp-(1→4)-α-L-GalpNAcA-(1→3)-β-D-GalpNAc-(1→.

  structure, NMR spectroscopy, O-specific polysaccharide, Marine bacteria, 2-acetamido-2-deoxy-L-galacturonic acid, Arenibacter palladensis

  NCBI PubMed ID: 22339637
  Publication DOI: 10.1134/S0006297912010105
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: tomsh@piboc.dvo.ru
  Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, 690022, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, mild acid hydrolysis, chemical methods
  
   
  
  Arenibacter palladensis KMM 3961 (T)
  CSDB ID 27341 (all data & tools)
• Article ID: 6300
  Qin CJ, Hou HL, Ding MR, Qi YK, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical synthesis of a synthetically useful L-galactosaminuronic acid building block" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(5) (2022) 387-392
  

  Most bacterial cell surface glycans are structurally unique, and have been considered as ideal target molecules for the developments of detection and diagnosis techniques, as well as vaccines. Chemical synthesis has been a promising approach to prepare well-defined oligosaccharides, facilitating the structure-activity relationship exploration and biomedical applications of bacterial glycans. L-Galactosaminuronic acid is a rare sugar that has been only found in cell surface glycans of gram-negative bacteria. Here, an orthogonally protected L-galactosaminuronic acid building block was designed and chemically synthesized. A synthetic strategy based on glycal addition and TEMPO/BAIB-mediated C6 oxidation served well for the transformation of commercial L-galactose to the corresponding L-galactosaminuronic acid. Notably, the C6 oxidation of the allyl glycoside was more efficient than that of the selenoglycoside. In addition, a balance between the formation of allyl glycoside and the recovery of selenoglycoside was essential to improve efficiency of the NIS/TfOH-catalyzed allylation. This synthetically useful L-galactosaminuronic acid building block will provide a basis for the syntheses of complex bacterial glycans.

  chemical synthesis, C6 oxidation, glycal addition, L-galactosaminuronic acid, orthogonal protection

  NCBI PubMed ID: 35551773
  Publication DOI: 10.1016/S1875-5364(22)60149-3
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: Jian Yin
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MS, UV
  
   
  
  Arenibacter palladensis KMM 3961T
  CSDB ID 21140 (all data & tools)