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

Quentin Pavic (1) , Sylvain Tranchimand (1) , Loïc Lemiègre (1) , Laurent Legentil (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Domaines: Chimie

Quentin Pavic, Sylvain Tranchimand, Loïc Lemiègre, Laurent Legentil. Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses. Chemical Communications, 2018, 54 (44), pp.5550-5553. ⟨10.1039/c8cc01726c⟩. ⟨hal-01807886⟩