Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses

Chemical Communications : Chem Comm
Quentin PavicLaurent Legentil

Abstract

An arabinofuranosylhydrolase from the GH51 family was transformed into an acyl transferase by mutation of the catalytic acid/base amino acid. The resulting enzyme was able to transfer carboxylic acid onto the anomeric position of arabinose with complete chemo- and stereoselectivity. A wide range of acyl α-l-arabinofuranoses was obtained with yields ranging from 25 to 83%. Using this method, ibuprofen and N-Boc phenylalanine were successfully transformed into their corresponding acyl conjugates, expanding the scope of the reaction to drugs and amino acids.

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Citations

Dec 29, 2020·Current Opinion in Chemical Biology·Claire MoulisMagali Remaud-Siméon
Sep 27, 2020·Nature Communications·Manuel Nieto-DomínguezMaría Jesús Martínez

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Methods Mentioned

BETA
acylation
transglycosylation
NMR
column chromatography
glycosylation

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