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

[Image: see text] 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 y...

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Autores principales: Ebrecht, Ana C., Mofokeng, Thato M., Hollmann, Frank, Smit, Martha S., Opperman, Diederik J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353034/
https://www.ncbi.nlm.nih.gov/pubmed/37389482
http://dx.doi.org/10.1021/acs.orglett.3c01601
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author Ebrecht, Ana C.
Mofokeng, Thato M.
Hollmann, Frank
Smit, Martha S.
Opperman, Diederik J.
author_facet Ebrecht, Ana C.
Mofokeng, Thato M.
Hollmann, Frank
Smit, Martha S.
Opperman, Diederik J.
author_sort Ebrecht, Ana C.
collection PubMed
description [Image: see text] 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.
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spelling pubmed-103530342023-07-19 Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids Ebrecht, Ana C. Mofokeng, Thato M. Hollmann, Frank Smit, Martha S. Opperman, Diederik J. Org Lett [Image: see text] 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. American Chemical Society 2023-06-30 /pmc/articles/PMC10353034/ /pubmed/37389482 http://dx.doi.org/10.1021/acs.orglett.3c01601 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ebrecht, Ana C.
Mofokeng, Thato M.
Hollmann, Frank
Smit, Martha S.
Opperman, Diederik J.
Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title_full Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title_fullStr Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title_full_unstemmed Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title_short Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids
title_sort lactones from unspecific peroxygenase-catalyzed in-chain hydroxylation of saturated fatty acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10353034/
https://www.ncbi.nlm.nih.gov/pubmed/37389482
http://dx.doi.org/10.1021/acs.orglett.3c01601
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