(S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones

Chem Commun (Camb). 2013 Mar 11;49(20):2061-3. doi: 10.1039/c3cc38607d.

Abstract

We report the first rationally designed (S)-selective MenD from E. coli for the synthesis of functionalized α-hydroxy ketones. By mutation of two amino acids in the active site stereoselectivity of the (R)-selective EcMenD (ee > 93%) was inverted giving access to (S)-5-hydroxy-4-oxo-5-phenylpentanoate derivatives with stereoselectivities up to 97% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Biocatalysis
  • Catalytic Domain
  • Escherichia coli / metabolism*
  • Escherichia coli Proteins / genetics
  • Escherichia coli Proteins / metabolism*
  • Ketones / chemistry
  • Ketones / metabolism*
  • Mutation
  • Pyruvate Oxidase / genetics
  • Pyruvate Oxidase / metabolism*
  • Stereoisomerism

Substances

  • Aldehydes
  • Escherichia coli Proteins
  • Ketones
  • 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexadiene-1-carboxylate synthase, E coli
  • Pyruvate Oxidase