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.
Wuyuan Zhang  #  1  2 ,  Jeong-Hoo Lee  #  3 ,  Sabry H H Younes  1  4 ,  Fabio Tonin  1 ,  Peter-Leon Hagedoorn  1 ,  Harald Pichler  5 ,  Yoonjin Baeg  3 ,  Jin-Byung Park  6 ,  Robert Kourist  7 ,  Frank Hollmann  8
Affiliations
  • 1. Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands.
  • 2. School of Chemical Engineering and Technology, Xi'an Jiaotong University, 710049, Xi'an, China.
  • 3. Department of Food Science & Engineering, Ewha Womans University, Seoul, 03760, Republic of Korea.
  • 4. Chemistry Department, Faculty of Science, Sohag University, Sohag, 82524, Egypt.
  • 5. Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, 8010, Graz, Austria.
  • 6. Department of Food Science & Engineering, Ewha Womans University, Seoul, 03760, Republic of Korea. [email protected].
  • 7. Institute of Molecular Biotechnology, Graz University of Technology, Petersgasse 14, 8010, Graz, Austria. [email protected].
  • 8. Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629 HZ, Delft, The Netherlands. [email protected].
  • # Contributed equally.
PMID: 32382158 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.

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