Synthesis of Short-Chain Diols and Unsaturated Alcohols From Secondary Alcohol Substrates by the Rieske Nonheme Mononuclear Iron Oxygenase MdpJ

Appl Environ Microbiol. 2012 Sep;78(17):6280-4. doi: 10.1128/AEM.01434-12. Epub 2012 Jun 29.

Abstract

The Rieske nonheme mononuclear iron oxygenase MdpJ of the fuel oxygenate-degrading bacterial strain Aquincola tertiaricarbonis L108 has been described to attack short-chain tertiary alcohols via hydroxylation and desaturation reactions. Here, we demonstrate that also short-chain secondary alcohols can be transformed by MdpJ. Wild-type cells of strain L108 converted 2-propanol and 2-butanol to 1,2-propanediol and 3-buten-2-ol, respectively, whereas an mdpJ knockout mutant did not show such activity. In addition, wild-type cells converted 3-methyl-2-butanol and 3-pentanol to the corresponding desaturation products 3-methyl-3-buten-2-ol and 1-penten-3-ol, respectively. The enzymatic hydroxylation of 2-propanol resulted in an enantiomeric excess of about 70% for the (R)-enantiomer, indicating that this reaction was favored. Likewise, desaturation of (R)-2-butanol to 3-buten-2-ol was about 2.3-fold faster than conversion of the (S)-enantiomer. The biotechnological potential of MdpJ for the synthesis of enantiopure short-chain alcohols and diols as building block chemicals is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / metabolism*
  • Betaproteobacteria / enzymology*
  • Biotransformation
  • Electron Transport Complex III / genetics
  • Electron Transport Complex III / metabolism*
  • Gene Knockout Techniques
  • Hydroxylation
  • Oxygenases / genetics
  • Oxygenases / metabolism*

Substances

  • Alcohols
  • Rieske iron-sulfur protein
  • Oxygenases
  • Electron Transport Complex III