Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Nat Commun. 2020 May 7;11(1):2258. doi: 10.1038/s41467-020-16099-7.

Abstract

En route to a bio-based chemical industry, the conversion of fatty acids into building blocks is of particular interest. Enzymatic routes, occurring under mild conditions and excelling by intrinsic selectivity, are particularly attractive. Here we report photoenzymatic cascade reactions to transform unsaturated fatty acids into enantiomerically pure secondary fatty alcohols. In a first step the C=C-double bond is stereoselectively hydrated using oleate hydratases from Lactobacillus reuteri or Stenotrophomonas maltophilia. Also, dihydroxylation mediated by the 5,8-diol synthase from Aspergillus nidulans is demonstrated. The second step comprises decarboxylation of the intermediate hydroxy acids by the photoactivated decarboxylase from Chlorella variabilis NC64A. A broad range of (poly)unsaturated fatty acids can be transformed into enantiomerically pure fatty alcohols in a simple one-pot approach.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry
  • Biological Products / metabolism
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / metabolism*
  • Fatty Alcohols / chemistry*
  • Fatty Alcohols / metabolism*
  • Limosilactobacillus reuteri / metabolism
  • Stenotrophomonas maltophilia / metabolism
  • Substrate Specificity

Substances

  • Biological Products
  • Fatty Acids, Unsaturated
  • Fatty Alcohols