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Keywords:

Science & Technology, Physical Sciences, Chemistry, Applied, Chemistry, Organic, Chemistry, beta-amino acids, biotransformations, enantioselectivity, phenylalanine aminomutase, phenylalanine ammonia lyase, tandem reactions, PHENYLALANINE AMINOMUTASE, MECHANISM, AMMONIA, EXPRESSION, RESIDUE, CLONING, 0302 Inorganic Chemistry, 0305 Organic Chemistry, 0904 Chemical Engineering, Organic Chemistry, 3405 Organic chemistry

Abstract:

We describe a simple and efficient enzymatic tandem reaction for the preparation of enantiomerically pure β-phenylalanine and its analogues from the corresponding racemates. In this process, phenylalanine aminomutase (PAM) catalyzes the stereoselective isomerization of (R)-β-phenylalanines to (S)-a-phenylalanines, which are in situ transformed to cinnamic acids by phenylalanine ammonia lyase (PAL). Preparative scale conversions are done with a mutated PAM with enhanced catalytic activity. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.