Penicillin Acylase-Catalyzed Effective and Stereoselective Acylation of 1-phenylethylamine in Aqueous Medium using Non-Activated Acyl Donor

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Abstract


Until recently the biocatalytic preparation of enantiomerically pure amines was based on stereoselective acyl transfer in an organic medium using activated acyl donors. The possibility of performing an effective and enantioselective enzymatic acylation of amines in an aqueous medium without using activated acyl donors was demonstrated for the first time as the example of direct condensation of phenylacetic acid and racemic 1-phenylethylamine. Direct condensation of the acid and the amine took place at mild reaction conditions with a high initial rate (3.3 μmole/(l∙h)), degree of conversion (80% acylation of active amine enantiomer), and enantioselectivity (enantiomeric excess of the product was more than 95%). The suggested approach has remarkable advantages compared to enzymatic reactions in organic media and is of practical value for the biocatalytic preparation of enantiomerically pure compounds at mild conditions using readily available reagents.

Penicillin Acylase-Catalyzed Effective and Stereoselective Acylation of 1-phenylethylamine in Aqueous Medium using Non-Activated Acyl Donor

D T Guranda

Belozersky Institute of Physicochemical Biology

Faculty of Bioengineering and Bioinformatics

G A Ushakov

Belozersky Institute of Physicochemical Biology

Faculty of Bioengineering and Bioinformatics

V K Svedas

Lomonosov Moscow State University

Email: vytas@belozersky.msu.ru
Russia

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Copyright (c) 2010 Guranda D.T., Ushakov G.A., Svedas V.K.

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