Regioselective Biocatalytic Hydroxylation of Fatty Acids by Cytochrome P450s

Regioselective Biocatalytic Hydroxylation of Fatty Acids by Cytochrome P450s Keywords Biocatalysis · Enzymes · Hydroxylation · C–H bond activation · Fatty acid · Cytochrome P450 1 Introduction olefin-cyclopropanation via carbene transfer under oxygen- free conditions [11], enantioselective intramolecular ben- Cytochrome P450 enzymes (CYPs) are iron (Fe) contain- zylic C–H amination [12], and carbon-silicon bond forma- ing heme-proteins, which are found in most living organ- tion [13], all reactions, which have not been found in nature isms, including eukaryotes, archaea, bacteria, and viruses before. [1–4]. The enzymes catalyze a broad range of reactions This enormous repertoire of different C–H-activation such as hydroxylation [5], decarboxylation [6], epoxi- reactions renders P450s highly interesting for industrial dation [7], reductive dehalogenation [8], amine/oxygen applications [14–16]. However, low turnover rates, the dealkylation [9], and sulfoxidation [10], employing molec- requirement of complex electron transfer systems and ular oxygen and electrons [e.g. from NAD(P)H]. Further- cofactor regeneration complicate the synthetic application more, engineered P450 were reported to catalyze selective of P450s for the production of valuable fine chemicals and consequently more efficient family members are required for bulk applications [14, 17, 18]. Fatty acids represent the natural substrates for several * Wolfgang Kroutil wolfgang.kroutil@uni-graz.at classes of cytochrome P450s and their regioselective C–H functionalization gives access to hydroxy-fatty acids which Austrian Centre http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Catalysis Letters Springer Journals

Regioselective Biocatalytic Hydroxylation of Fatty Acids by Cytochrome P450s

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Publisher
Springer US
Copyright
Copyright © 2017 by The Author(s)
Subject
Chemistry; Catalysis; Industrial Chemistry/Chemical Engineering; Organometallic Chemistry; Physical Chemistry
ISSN
1011-372X
eISSN
1572-879X
D.O.I.
10.1007/s10562-017-2273-4
Publisher site
See Article on Publisher Site

Abstract

Keywords Biocatalysis · Enzymes · Hydroxylation · C–H bond activation · Fatty acid · Cytochrome P450 1 Introduction olefin-cyclopropanation via carbene transfer under oxygen- free conditions [11], enantioselective intramolecular ben- Cytochrome P450 enzymes (CYPs) are iron (Fe) contain- zylic C–H amination [12], and carbon-silicon bond forma- ing heme-proteins, which are found in most living organ- tion [13], all reactions, which have not been found in nature isms, including eukaryotes, archaea, bacteria, and viruses before. [1–4]. The enzymes catalyze a broad range of reactions This enormous repertoire of different C–H-activation such as hydroxylation [5], decarboxylation [6], epoxi- reactions renders P450s highly interesting for industrial dation [7], reductive dehalogenation [8], amine/oxygen applications [14–16]. However, low turnover rates, the dealkylation [9], and sulfoxidation [10], employing molec- requirement of complex electron transfer systems and ular oxygen and electrons [e.g. from NAD(P)H]. Further- cofactor regeneration complicate the synthetic application more, engineered P450 were reported to catalyze selective of P450s for the production of valuable fine chemicals and consequently more efficient family members are required for bulk applications [14, 17, 18]. Fatty acids represent the natural substrates for several * Wolfgang Kroutil wolfgang.kroutil@uni-graz.at classes of cytochrome P450s and their regioselective C–H functionalization gives access to hydroxy-fatty acids which Austrian Centre

Journal

Catalysis LettersSpringer Journals

Published: Dec 21, 2017

References

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