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

Organic & Biomolecular Chemistry Pub Date: 2020-02-27 DOI: 10.1039/D0OB00240B

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
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