N-Alkyl-α-amino acids in Nature and their biocatalytic preparation

Julia F. Hyslop, Sarah L. Lovelock, Allan J.B. Watson, Peter W. Sutton, Gheorghe Doru Roiban

Research output: Contribution to journalReview articleResearch

5 Citations (Scopus)

Abstract

© 2019 Elsevier B.V. N-Alkylated-α-amino acids are useful building blocks for the pharmaceutical and fine chemical industries. Enantioselective methods of N-alkylated-α-amino acid synthesis are therefore highly valuable and widely investigated. While there are a variety of chemical methods for their synthesis, they often employ stoichiometric quantities of hazardous reagents such as pyrophoric metal hydrides or genotoxic alkylating agents, whereas biocatalytic routes can provide a greener and cleaner alternative to existing methods. This review highlights the occurrence of the N-alkyl-α-amino acid motif and its role in nature, important applications towards human health and biocatalytic methods of preparation. Several enzyme classes that can be used to access chiral N-alkylated-α-amino acids and their substrate selectivities are detailed.
Original languageEnglish
Pages (from-to)56-65
Number of pages10
JournalJournal of Biotechnology
Volume293
DOIs
Publication statusPublished - 10 Mar 2019

Keywords

  • Biocatalysis
  • Dehydrogenases
  • N-Alkyl-α-amino acids
  • N-Methyl transferases
  • Nature
  • Animals
  • Humans
  • Amino Acids/biosynthesis
  • PROTEIN METHYLATION
  • PSEUDOMONAS-PUTIDA
  • N-Alkyl-alpha-amino acids
  • ENZYMATIC-SYNTHESIS
  • PHENYLALANINE AMMONIA-LYASE
  • PYRROLINE-5-CARBOXYLATE REDUCTASE
  • SUBSTITUTED ASPARTIC ACIDS
  • ENANTIOSELECTIVE REDUCTIVE AMINATION
  • OPINE DEHYDROGENASE
  • OCTOPINE DEHYDROGENASE
  • IMINE REDUCTASES

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