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Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions
Author(s) -
de Leeuw Nicolas,
Torrelo Guzman,
Bisterfeld Carolin,
Resch Verena,
Mestrom Luuk,
Straulino Emanuele,
van der Weel Laura,
Hanefeld Ulf
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701282
Subject(s) - chemistry , mycobacterium smegmatis , hydrolysis , acylation , kinetic resolution , enantiomer , transesterification , acyl group , transferase , lipase , cyanohydrin , enzyme , organic chemistry , catalysis , stereochemistry , enantioselective synthesis , alkyl , mycobacterium tuberculosis , medicine , tuberculosis , pathology
The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [( R );E>37 and ( S );E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses.