Biocatalytic synthesis of chiral N-functionalized amino acids

Julia Hyslop, Sarah L Lovelock, Peter Sutton, Kristin K Brown, Allan J. B. Watson, Gheorghe-Doru Roiban

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)
3 Downloads (Pure)

Abstract

N-functionalized amino acids are important building blocks for the preparation of diverse bioactive molecules including peptides. The development of sustainable manufacturing routes to chiral N-alkylated amino acids remains a significant challenge in the pharmaceutical and fine chemical industries. Herein we report the discovery of a structurally diverse panel of biocatalysts which catalyze the asymmetric synthesis of N-alkyl amino acids via the reductive coupling of ketones and amines. Reactions have been performed on a gram scale to yield optically pure N-alkyl functionalized products in high yields.
Original languageEnglish
JournalAngewandte Chemie International Edition
VolumeEarly View
Early online date21 Sept 2018
DOIs
Publication statusE-pub ahead of print - 21 Sept 2018

Keywords

  • N-methyl amino acid deyhydrogenases
  • Ketimine reductases
  • α-keto amino acids
  • Biocatalysis
  • Reductive amination

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