Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ]
The structure was elucidated in this paperNCBI PubMed ID: 37603587Publication DOI: 10.1021/acs.orglett.3c02430Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: S.S. Kulkarni <suvarn
chem.iitb.ac.in>
Institutions: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India
Herein we report the first total synthesis of a densely functionalized tetrasaccharide repeating unit of Vibrio cholerae O43, which contains rare deoxy amino sugars d-quinovosamine and d-viosamine attached with the rare amino acid N-acetyl-l-allothreonine. Synthesis of orthogonally protected rare sugars and unnatural amino acid building blocks, stereoselective construction of three consecutive 1,2-cis glycosidic linkages, amide coupling, and the presence of five nitrogen atoms dispersed over four sugar units as well as the carboxylic acid functionality make the total synthesis a formidable task.
repeating unit, O-polysaccharide, total synthesis, V.cholerae O43
Structure type: oligomer ; 1042.3955 [M+Na]+
C
43H
65N
5O
23Location inside paper: Scheme 1, p. 6416, p. S25, compound 1
Aglycon: p-methoxy-phenyl
Compound class: O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_885822
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, FTIR, UV, glycosylation, optical rotation measurement, HR-ESI-MS
Synthetic data: chemical
Comments, role: the tetrasaccharide repeating unit of V. cholerae O43
Related record ID(s): 22290
NCBI Taxonomy refs (TaxIDs): 666
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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