Enzymatic Synthesis of Methylated Terpene Analogues Using the Plasticity of Bacterial Terpene Synthases

Chemistry. 2020 Feb 17;26(10):2178-2182. doi: 10.1002/chem.201905827. Epub 2020 Jan 30.

Abstract

Methylated analogues of isopentenyl diphosphate were synthesised and enzymatically incorporated into methylated terpenes. A detailed stereochemical analysis of the obtained products is presented. The methylated terpene precursors were also used in conjunction with various isotopic labellings to gain insights into the mechanisms of their enzymatic formation.

Keywords: configuration determination; enzyme catalysis; isotopes; substrate analogues; terpenoids.

MeSH terms

  • Alkyl and Aryl Transferases / metabolism*
  • Bacteria / enzymology*
  • Bacterial Proteins / metabolism*
  • Chloroflexi / enzymology
  • Chryseobacterium / enzymology
  • Hemiterpenes / chemical synthesis
  • Hemiterpenes / chemistry
  • Hemiterpenes / metabolism
  • Methylation
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / metabolism
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / metabolism*

Substances

  • Bacterial Proteins
  • Hemiterpenes
  • Organophosphorus Compounds
  • Terpenes
  • isopentenyl pyrophosphate
  • Alkyl and Aryl Transferases
  • terpene synthase

Supplementary concepts

  • Roseiflexus castenholzii