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Enzyme catalysed hydrolysis of dialkylated propanedioic acid diesters,chain length dependent reversal of enantioselectivity
Authors:Fredrik Björkling  John Boutelje  Sten Gatenbeck  Karl Hult  Torbjŏrn Norin  Peter Szmulik
Affiliation:1. Department of Organic Chemistry, Royal Institute of Technology, S-100 44 StockholmSweden;2. Department of Biochemistry and Biotechnology Royal Institute of Technology, S-100 44 StockholmSweden
Abstract:Enzyme catalysed hydrolyses of dialkylated propanedioic acid diesters have been studied. A novel change of enantioselectivity from pro-S to pro-R in the hydrolysis of ester groups was observed, depending on the chain length of the alkyl substituents of the substrate. Optically pure (S)-(-)-α-methylphenylalanine was prepared by α-chymotrypsin catalysed hydrolysis of benzylmethylpropanedioic acid dimethyl ester.
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