Synthesis of fluorinated Exo-glycals mediated by selectfluor

Guillaume Eppe, Audrey Caravano, Jérôme Désiré, Stéphane P. Vincent

Research output: Contribution in Book/Catalog/Report/Conference proceedingChapter

Abstract

Fluorinated carbohydrates constitute a very important class of mechanistic probes for glycosyl processing enzymes. In the mechanistic studies of retaining glycosidases, 2-fluoro-glycosides have become key tools to evidence a transient covalent process as well as to identify the catalytic nucleophiles. Fluorinated sugars have also been successfully exploited as mechanistic probes for glycosyltransferases. Exo-glycals are anomeric enol-ethers derived from carbohydrates in which the double bond is exocyclic. This class of molecules has found many applications as synthetic intermediates. In addition, some exo-glycals have been designed as transition-state analogues of enzymatic glycosyl transfers and were shown to be extremely potent sialyltransferase inhibitors. Interestingly, exo-glycals derived from galactofuranose (Galf) displayed unique time-dependent inactivation properties against UDP-galactopyranose mutase (UGM), an essential enzyme implied in the biosynthesis of the cell wall of important pathogens. Importantly, we could show that the corresponding fluorinated exo-glycal improved the properties of these inhibitors. Beyond carbohydrate chemistry, phosphonates and their fluorinated analogues constitute a very important class of molecules that have found applications in both material and pharmaceutical sciences.

Original languageEnglish
Title of host publicationCarbohydrate Chemistry
Subtitle of host publicationProven Synthetic Methods
EditorsGijsbert Van der Marel, Jeroen Codee
PublisherCRC Press
Chapter12
Pages85-96
Number of pages12
Volume2
ISBN (Electronic)9780429064487
ISBN (Print)9781439875940
DOIs
Publication statusPublished - 4 Mar 2014

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    Eppe, G., Caravano, A., Désiré, J., & Vincent, S. P. (2014). Synthesis of fluorinated Exo-glycals mediated by selectfluor. In G. Van der Marel, & J. Codee (Eds.), Carbohydrate Chemistry: Proven Synthetic Methods (Vol. 2, pp. 85-96). CRC Press. https://doi.org/10.1201/b16602