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Issue 44, 2018
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Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses

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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.

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

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Article information


Submitted
02 Mar 2018
Accepted
01 May 2018
First published
03 May 2018

Chem. Commun., 2018,54, 5550-5553
Article type
Communication

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

Q. Pavic, S. Tranchimand, L. Lemiègre and L. Legentil, Chem. Commun., 2018, 54, 5550
DOI: 10.1039/C8CC01726C

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