Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS 
]
The structure was elucidated in this paperNCBI PubMed ID: 37340701Publication DOI: 10.1021/acs.joc.3c00615Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: A. Santa <asantra
iict.res.in>
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
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
Structure type: oligomer ; 983.3759 [M-H]-
C
41H
63N
2O
25Location inside paper: abstract, scheme 1, scheme 8, structure 1
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
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, glycosylation, optical rotation measurement, CC, HR-ESI-MS, DEPT-135
Synthetic data: chemical
Comments, role: pentasaccharide repeating unit of A. baumannii K11 CPS
NCBI Taxonomy refs (TaxIDs): 470
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error