1. Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses.
- Author
-
Pavic Q, Tranchimand S, Lemiègre L, and Legentil L
- Subjects
- Arabinose analogs & derivatives, Arabinose chemistry, Biocatalysis, Glycoside Hydrolases chemistry, Molecular Structure, Arabinose biosynthesis, Glycoside Hydrolases metabolism
- 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.
- Published
- 2018
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