Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
NCBI PubMed ID: 25807254Publication DOI: 10.1021/acs.joc.5b00139Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: nakamura
phar.nagoya-cu.ac.jp; hsmt
pharm.hokudai.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
The first convergent synthesis of the tetrasaccharide repeating unit of the polymeric O antigen isolated from Acinetobacter baumannii serogroup O18 has been achieved. The ManNAc β1→4 Gal and GalNAc β1→3 Gal units were successfully obtained through beta-selective glycosylation with 2- azido-4,6-O-benzylidene-2-deoxymannosyl diphenyl phosphate and Tf2NH-promoted glycosylation with 2-acetamido-2-deoxygalactosyl diethyl phosphite, respectively. The disaccharide units could be coupled with the aid of TMSClO4 as an activator of the diphenyl phosphate leaving group, and global deprotection completed the synthesis of the tetrasaccharide.
O-antigen, Acinetobacter baumannii
Structure type: polymer chemical repeating unit
Location inside paper: p.4278, fig.1
Compound class: O-polysaccharide, O-antigen, CPS
Contained glycoepitopes: IEDB_130648,IEDB_130651,IEDB_134627,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_141794,IEDB_144987,IEDB_147450,IEDB_151528,IEDB_190606,IEDB_742247,IEDB_885813,SB_165,SB_166,SB_187,SB_195,SB_21,SB_23,SB_24,SB_31,SB_62,SB_7,SB_8,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, chemical methods, MS, glycosylation
Related record ID(s): 30917
NCBI Taxonomy refs (TaxIDs): 470Reference(s) to other database(s): GTC:G40148IO, GlycomeDB:
25205
Show glycosyltransferases
There is only one chemically distinct structure:
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