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

Wuyuan Zhang, Jeong-Hoo Lee, Sabry H. H. Younes, Fabio Tonin, Peter-Leon Hagedoorn, Harald Pichler, Yoonjin Baeg, Jin-Byung Park (), Robert Kourist () and Frank Hollmann ()
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Wuyuan Zhang: Delft University of Technology
Jeong-Hoo Lee: Ewha Womans University
Sabry H. H. Younes: Delft University of Technology
Fabio Tonin: Delft University of Technology
Peter-Leon Hagedoorn: Delft University of Technology
Harald Pichler: Graz University of Technology
Yoonjin Baeg: Ewha Womans University
Jin-Byung Park: Ewha Womans University
Robert Kourist: Graz University of Technology
Frank Hollmann: Delft University of Technology

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-16099-7

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