Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades

Research output: Contribution to journalArticle

  • External authors:
  • Curtis J.W. Walton
  • Janet E.B. Barber
  • Jenna L. McCann
  • Roberto A. Chica

Abstract

d-Phenylalanine derivatives are valuable chiral building blocks for a wide range of pharmaceuticals. Here, we developed stereoinversion and deracemization biocatalytic cascades to synthesize d-phenylalanine derivatives that contain electron-donating or -withdrawing substituents of various sizes and at different positions on the phenyl ring with a high enantiomeric excess (90 to >99 % ee) from commercially available racemic mixtures or l-amino acids. These whole-cell systems couple Proteus mirabilis l-amino acid deaminase with an engineered aminotransferase that displays native-like activity towards d-phenylalanine, which we generated from Bacillus sp. YM-1 d-amino acid aminotransferase. Our cascades are applicable to preparative-scale synthesis and do not require cofactor-regeneration systems or chemical reducing agents.

Bibliographical metadata

Original languageEnglish
Pages (from-to)470-474
Number of pages5
JournalChemCatChem
Volume10
Issue number2
Early online date18 Aug 2017
DOIs
Publication statusPublished - 5 Dec 2017