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; Frank Hollmann

doi:10.1038/s41467-020-16099-7

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, Frank Hollmann

Food Science and Biotechnology

Research output: Contribution to journal › Article › peer-review

52 Scopus citations

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.

Original language	English
Article number	2258
Journal	Nature Communications
Volume	11
Issue number	1
DOIs	https://doi.org/10.1038/s41467-020-16099-7
State	Published - 1 Dec 2020

Bibliographical note

Funding Information:
The Netherlands Organisation for Scientific Research (NWO) is gratefully acknowledged for financial support through a VICI grant (no. 724.014.003). W.Z. gratefully acknowledges financial support by “Young Talent Support Plan” of Xi’an Jiaotong University (No. 7121191208). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MEST) (No. 2020R1A2B5B03002376).

Publisher Copyright:
© 2020, The Author(s).

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title = "Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids",

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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AU - Hagedoorn, Peter Leon

AU - Pichler, Harald

AU - Baeg, Yoonjin

AU - Park, Jin Byung

AU - Kourist, Robert

AU - Hollmann, Frank

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N2 - 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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Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Abstract

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