Asymmetric β-Methylation of l- and d-α-Amino Acids by a Self-Contained Enzyme Cascade

Angew Chem Int Ed Engl. 2020 Apr 27;59(18):7184-7187. doi: 10.1002/anie.201916025. Epub 2020 Mar 11.

Abstract

This report describes a modular enzyme-catalyzed cascade reaction that transforms l- or d-α-amino acids to β-methyl-α-amino acids. In this process an α-amino acid transaminase, an α-keto acid methyltransferase, and a halide methyltransferase cooperate in two orthogonal reaction cycles that mediate product formation and regeneration of the cofactor pyridoxal-5'-phosphate and the co-substrate S-adenosylmethionine. The only stoichiometric reagents consumed in this process are the unprotected l- or d-α-amino acid and methyl iodide.

Keywords: S-adenosylmethionine; amino acids; biocatalysis; methyltransferase; stereoselective C-alkylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / metabolism*
  • Methylation
  • Methyltransferases / metabolism*
  • Molecular Structure
  • Stereoisomerism
  • Transaminases / metabolism*

Substances

  • Amino Acids
  • Methyltransferases
  • Transaminases