Issue 8, 2025

Synthesis of the conjugation-ready β-mannosamine-containing O-antigen repeat from Vibrio cholerae O14

Abstract

Chemical synthesis of the trisaccharide repeating unit of the O-antigen from Vibrio cholerae has been accomplished through a linear strategy. The reducing end 1,2-cis mannosamine unit has been achieved through the azide inversion of the 2-OH position of a suitably protected glucose moiety. The crucial (S)-3-hydroxybutyric acid is inserted successfully at the last stage through EDC–HOBt coupling. The target trisaccharide, in the form of its 2-aminoethyl glycoside, is ready for further conjugation.

Graphical abstract: Synthesis of the conjugation-ready β-mannosamine-containing O-antigen repeat from Vibrio cholerae O14

Supplementary files

Article information

Article type
Paper
Submitted
18 Dec 2024
Accepted
07 Jan 2025
First published
08 Jan 2025

Org. Biomol. Chem., 2025,23, 1866-1873

Synthesis of the conjugation-ready β-mannosamine-containing O-antigen repeat from Vibrio cholerae O14

S. Maiti and B. Mukhopadhyay, Org. Biomol. Chem., 2025, 23, 1866 DOI: 10.1039/D4OB02049A

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