Stereoselective synthesis of boat-locked glycosides designed as glycosyl hydrolase conformational probes

Emilie Thiery, Jérémy Reniers, Johan Wouters, Stéphane P. Vincent

Research output: Contribution to journalArticle

Abstract

A general method for the preparation of galactose derivatives locked in a <sup>1,4</sup>B boat conformation has been developed. The boat scaffold was stereoselectively functionalized at the C-1′ position by aliphatic and aromatic groups along with azido or hydroxy groups. The configuration at the new stereogenic center was controlled and determined by X-raydiffraction. These molecules were designed to probe the conformational itinerary of the substrate of glycosyl hydrolases. Inhibition assays were performed against a series of commercially available glycosidases, which showed that these enzymes do not harness a <sup>1,4</sup>B-boat-like transition state.

Original languageEnglish
Pages (from-to)1472-1484
Number of pages13
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number7
DOIs
Publication statusPublished - 2015

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Keywords

  • Carbohydrates
  • Conformation analysis
  • Enzymes
  • Inhibitors

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