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

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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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01807886
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Submitted on : Tuesday, June 5, 2018 - 11:57:30 AM
Last modification on : Wednesday, October 2, 2019 - 1:53:26 PM

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

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