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

Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses. Chem Commun (Camb). 2018 May 15;: Authors: Pavic Q, Tranchimand S, Lemiègre L, Legentil L 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. PMID: 29761808 [PubMed - as supplied by publisher]
Source: Chemical Communications - Category: Chemistry Authors: Tags: Chem Commun (Camb) Source Type: research