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

Wang, L.; Berni, F.; Enotarpi, J.; Overkleeft, H.S.; Marel, G.A. van der; Codée, J.D.C.

doi:doi:10.1039/d0ob00240b

Persistent URL of this record https://hdl.handle.net/1887/90095

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Leiden Institute of Chemistry (LIC)

Wang, L.; Berni, F.; Enotarpi, J.; Overkleeft, H.S.; Marel, G.A. van der; Codée, J.D.C. (2020)

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

Article / Letter to editor

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.