Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin

J Am Chem Soc. 2006 Jun 28;128(25):8128-9. doi: 10.1021/ja062669x.

Abstract

Geosmin is responsible for the characteristic odor of moist soil. Incubation of recombinant germacradienol synthase, encoded by the SCO6073 (SC9B1.20) gene of the Gram-positive soil bacterium Streptomyces coelicolor, with farnesyl diphosphate (2, FPP) in the presence of Mg2+ gave a mixture of (4S,7R)-germacra-1(10)E,5E-diene-11-ol (3) (74%), (-)-(7S)-germacrene D (4) (10%), geosmin (1) (13%), and a hydrocarbon, tentatively assigned the structure of octalin 5 (3%). Individual incubations of recombinant germacradienol synthase with [1,1-2H2]FPP (2a), (1R)-[1-2H]-FPP (2b), and (1S)-[1-2H]-FPP (2c), as well as with FPP (2) in D2O, and GC-MS analysis of the resulting deuterated products supported a mechanism of geosmin formation involving proton-initiated cyclization and retro-Prins fragmentation of the initially formed germacradienol to give intermediate 5, followed by protonation of 5, 1,2-hydride shift, and capture of water.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkyl and Aryl Transferases / chemistry*
  • Alkyl and Aryl Transferases / genetics
  • Alkyl and Aryl Transferases / metabolism
  • Cyclization
  • Mass Spectrometry
  • Molecular Structure
  • Naphthols / chemical synthesis
  • Naphthols / chemistry*
  • Naphthols / metabolism
  • Polyisoprenyl Phosphates / chemistry*
  • Polyisoprenyl Phosphates / metabolism
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / metabolism
  • Streptomyces coelicolor / enzymology*

Substances

  • Naphthols
  • Polyisoprenyl Phosphates
  • Recombinant Proteins
  • Sesquiterpenes
  • germacradienol
  • farnesyl pyrophosphate
  • Alkyl and Aryl Transferases
  • germacrene D synthase
  • geosmin