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| Research article summary (published 24 Jan 2009): |
Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivatives.
Full Abstract
The phenylalanine aminomutase (PAM) from Taxus chinensis catalyses the conversion of alpha-phenylalanine to beta-phenylalanine, an important step in the biosynthesis of the N-benzoyl phenylisoserinoyl side-chain of the anticancer drug taxol. Mechanistic studies on PAM have suggested that (E)-cinnamic acid is an intermediate in the mutase reaction and that it can be released from the enzyme's active site. Here we describe a novel synthetic strategy that is based on the finding that ring-substituted (E)-cinnamic acids can serve as a substrate in PAM-catalysed ammonia addition reactions for the biocatalytic production of several important beta-amino acids. The enzyme has a broad substrate range and a high enantioselectivity with cinnamic acid derivatives; this allows the synthesis of several non-natural aromatic alpha- and beta-amino acids in excellent enantiomeric excess (ee >99 %). The internal 5-methylene-3,5-dihydroimidazol-4-one (MIO) cofactor is essential for the PAM-catalysed amination reactions. The regioselectivity of amination reactions was influenced by the nature of the ring substituent.
Author information
Author/s: Wu, Bian (B); Szymanski, Wiktor (W); Wietzes, Piet (P); de Wildeman, Stefaan (S); Poelarends, Gerrit J (GJ); Feringa, Ben L (BL); Janssen, Dick B (DB);
Affiliation: Department of Biochemistry, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Journal and publication information
Publication Type: Journal Article; Research Support, Non-U.S. Gov't
Journal: Chembiochem : a European journal of chemical biology (Chembiochem), published in Germany. (Language: eng)
Reference: 2009-Jan; vol 10 (issue 2) : pp 338-44
Dates: Created 2009/01/21; Completed 2009/03/05;
PMID: 19123196, status: MEDLINE (last retrieval date: 3/10/2009, IMS Date: )
Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.
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