Issue 11, 2020

Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

Abstract

The stereoselective construction of 1,2-cis-glycosidic linkages is key in the assembly of biologically relevant glycans, but remains a synthetic challenge. Reagent-controlled glycosylation methodologies, in which external nucleophiles are employed to modulate the reactivity of the glycosylation system, have become powerful means for the construction of 1,2-cis-glycosidic linkages. Here we establish that nucleophilic additives can support the construction of α-1,2-glucans, and apply our findings in the construction of a D-alanine kojibiose functionalized glycerol phosphate teichoic acid fragment. This latter molecule can be found in the cell wall of the opportunistic Gram-positive bacterium, Enterococcus faecalis and represents a structural element that can possibly be used in the development of therapeutic vaccines and diagnostic tools.

Graphical abstract: Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

Supplementary files

Article information

Article type
Communication
Submitted
04 feb 2020
Accepted
25 feb 2020
First published
27 feb 2020
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2020,18, 2038-2050

Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

L. Wang, F. Berni, J. Enotarpi, H. S. Overkleeft, G. van der Marel and J. D. C. Codée, Org. Biomol. Chem., 2020, 18, 2038 DOI: 10.1039/D0OB00240B

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