Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1016/j.tet.2022.132948Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: K. Misra <akmisra69
gmail.com>
Institutions: Bose Institute, Division of Molecular Medicine, Block EN-80, Sector-V, Salt Lake, Kolkata, 700091, India
A concise synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit of the capsular polysaccharide of Escherichia coli (E.coli) strain applying block [2+3] stereoselective glycosylation. A functionalized disaccharide thioglycoside donor prepared using 'armed-disarmed' glycosylation concept, was coupled with suitably protected trisaccharide glycosyl acceptor in the presence of a combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4–SiO2) to give the target pentasaccharide derivative in 65% yield. A late-stage regioselective oxidation of the primary hydroxyl group using a combination of TEMPO and Bis(acetoxy)iodobenzene (BAIB) furnished d-galacturonic acid moiety in the functionalized pentasaccharide derivative.
synthesis, polysaccharide, pentasaccharide, glycosylation, oxidation, E.coli, HClO4-SiO2
Structure type: oligomer ; 973.3274 [M+H]+
C
39H
59NO
27Location inside paper: abstract, Fig. 1, scheme 5, structure 1
Aglycon: p-methoxyphenyl
Compound class: CPS
Contained glycoepitopes: IEDB_130422,IEDB_130701,IEDB_135813,IEDB_136105,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_144983,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_44,SB_67,SB_7,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, glycosylation, optical rotation measurement, HR-ESI-MS, DEPT
Comments, role: repeat unit of the CPS
NCBI Taxonomy refs (TaxIDs): 562
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error