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

Wiktor Szymanski, Bian Wu, Barbara Weiner, Stefaan de Wildeman, B.L. Feringa, Dick B. Janssen

OnderzoeksoutputAcademicpeer review

65 Citaten (Scopus)

Samenvatting

An approach is described for the synthesis of aromatic alpha- and beta-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 alpha- and beta-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.

Originele taal-2English
Pagina's (van-tot)9152-9157
Aantal pagina's6
TijdschriftJournal of Organic Chemistry
Volume74
Nummer van het tijdschrift23
DOI's
StatusPublished - 4-dec-2009

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