Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids

Ana C. Ebrecht; Thato M. Mofokeng; Frank Hollmann; Martha S. Smit; Diederik J. Opperman

doi:10.1021/acs.orglett.3c01601

Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids

Ana C. Ebrecht, Thato M. Mofokeng, Frank Hollmann, Martha S. Smit, Diederik J. Opperman^*

^*Corresponding author for this work

BT/Biocatalysis

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

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Abstract

γ- and δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8-C12 fatty acids to yield after lactonization the corresponding γ- and δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones as the major products. Overoxidation of the hydroxy fatty acids was addressed via the reduction of the resulting oxo acids using an alcohol dehydrogenase in a bienzymatic cascade reaction.

Original language	English
Pages (from-to)	4990-4995
Journal	Organic Letters
Volume	25
Issue number	27
DOIs	https://doi.org/10.1021/acs.orglett.3c01601
Publication status	Published - 2023

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acs.orglett.3c01601Final published version, 1.88 MBLicence: CC BY

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title = "Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids",

abstract = "γ- and δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8-C12 fatty acids to yield after lactonization the corresponding γ- and δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones as the major products. Overoxidation of the hydroxy fatty acids was addressed via the reduction of the resulting oxo acids using an alcohol dehydrogenase in a bienzymatic cascade reaction.",

author = "Ebrecht, {Ana C.} and Mofokeng, {Thato M.} and Frank Hollmann and Smit, {Martha S.} and Opperman, {Diederik J.}",

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language = "English",

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T1 - Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids

AU - Ebrecht, Ana C.

AU - Mofokeng, Thato M.

AU - Hollmann, Frank

AU - Smit, Martha S.

AU - Opperman, Diederik J.

PY - 2023

Y1 - 2023

N2 - γ- and δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8-C12 fatty acids to yield after lactonization the corresponding γ- and δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones as the major products. Overoxidation of the hydroxy fatty acids was addressed via the reduction of the resulting oxo acids using an alcohol dehydrogenase in a bienzymatic cascade reaction.

AB - γ- and δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8-C12 fatty acids to yield after lactonization the corresponding γ- and δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones as the major products. Overoxidation of the hydroxy fatty acids was addressed via the reduction of the resulting oxo acids using an alcohol dehydrogenase in a bienzymatic cascade reaction.

UR - http://www.scopus.com/inward/record.url?scp=85164770578&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.3c01601

DO - 10.1021/acs.orglett.3c01601

M3 - Article

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AN - SCOPUS:85164770578

SN - 1523-7060

VL - 25

SP - 4990

EP - 4995

JO - Organic Letters

JF - Organic Letters

IS - 27

ER -

Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids

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