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

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• 作者：Wiktor Szymanski ; Bian Wu ; Barbara Weiner ; Stefaan de Wildeman ; Ben L. Feringa ; Dick B. Janssen
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：December 4, 2009
• 年：2009
• 卷：74
• 期：23
• 页码：9152-9157
• 全文大小：782K
• 年卷期：v.74,no.23(December 4, 2009)
• ISSN：1520-6904

文摘

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