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

Author

Listed:
  • Wuyuan Zhang

    (Delft University of Technology
    Xi’an Jiaotong University)

  • Jeong-Hoo Lee

    (Ewha Womans University)

  • Sabry H. H. Younes

    (Delft University of Technology
    Faculty of Science, Sohag University)

  • 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)

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.

Suggested Citation

  • Wuyuan Zhang & Jeong-Hoo Lee & Sabry H. H. Younes & Fabio Tonin & Peter-Leon Hagedoorn & Harald Pichler & Yoonjin Baeg & Jin-Byung Park & Robert Kourist & Frank Hollmann, 2020. "Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-16099-7
    DOI: 10.1038/s41467-020-16099-7
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    Cited by:

    1. Chen, Bi-Shuang & Zeng, Yong-Yi & Liu, Lan & Chen, Lei & Duan, Peigao & Luque, Rafael & Ge, Ran & Zhang, Wuyuan, 2022. "Advances in catalytic decarboxylation of bioderived fatty acids to diesel-range alkanes," Renewable and Sustainable Energy Reviews, Elsevier, vol. 158(C).
    2. Ng, Wei Zhe & Chan, Eng-Seng & Gourich, Wail & Ooi, Chien Wei & Tey, Beng Ti & Song, Cher Pin, 2023. "Perspective on enzymatic production of renewable hydrocarbon fuel using algal fatty acid photodecarboxylase from Chlorella variabilis NC64A: Potentials and limitations," Renewable and Sustainable Energy Reviews, Elsevier, vol. 184(C).

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