Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

Chirality. 2016 Sep;28(9):623-7. doi: 10.1002/chir.22623. Epub 2016 Aug 5.

Abstract

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol () and decane-1,5-diol () into the corresponding γ- () and δ-decalactones () with yield of 80% and enantiomeric excess (ee) = 75% and ee = 90%, respectively. Among oxidation of meso diols, (-)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee = 76% as well as (-)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee = 90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623-627, 2016. © 2016 Wiley Periodicals, Inc.

Keywords: Bacteria; Rhodococcus erythropolis DSM 44534; diols; lactones; oxidation; stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biotransformation
  • Catalysis
  • Green Chemistry Technology / methods*
  • Lactones / chemistry*
  • Rhodococcus / chemistry*
  • Rhodococcus / metabolism
  • Stereoisomerism

Substances

  • Lactones