Phenylalanine Aminomutase-Catalyzed Addition of Ammonia to Substituted Cinnamic Acids: a Route to Enantiopure alpha- and beta-Amino Acids

作者: Wiktor Szymanski , Bian Wu , Barbara Weiner , Stefaan de Wildeman , Ben L. Feringa

DOI: 10.1021/JO901833Y

关键词:

摘要: An approach is described for the synthesis of aromatic α- and β-amino acids that uses phenylalanine aminomutase to catalyze a highly enantioselective addition ammonia substituted cinnamic acids. The reaction has broad scope yields β-phenylalanines with excellent enantiomeric excess. regioselectivity conversion determined by substituents present at ring. A box model enzyme active site proposed, derived from influence hydrophobicity on affinity toward various substrates.

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