Solar-driven biocatalytic C-hydroxylation through direct transfer of photoinduced electrons

Despite the immense potential of P450s, the dependence on the nicotinamide cofactor (NADPH) and NADPH-P450 reductase (CPR) limits their employment in the chemical industry. Here, we present a visible light-driven platform for biocatalytic C-hydroxylation reactions using natural flavin molecules, esp...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2019-02, Vol.21 (3), p.515-525
Main Authors: Le, Thien-Kim, Park, Jong Hyun, Choi, Da Som, Lee, Ga-Young, Choi, Woo Sung, Jeong, Ki Jun, Park, Chan Beum, Yun, Chul-Ho
Format: Article
Language:English
Subjects:
Chemical industry
Dependence
Electrons
Flavin mononucleotide
Green chemistry
Heme
Hydroxylation
Iron
Lauric acid
NADP
NADPH
Nicotinamide
Nitrophenol
Organic chemistry
Photoactivation
Reductase
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Summary:Despite the immense potential of P450s, the dependence on the nicotinamide cofactor (NADPH) and NADPH-P450 reductase (CPR) limits their employment in the chemical industry. Here, we present a visible light-driven platform for biocatalytic C-hydroxylation reactions using natural flavin molecules, especially flavin mononucleotide, as a photosensitizer. By employing visible light as a source of energy instead of the nicotinamide cofactor, the bacterial CYP102A1 heme domain was successfully applied for photobiocatalytic C-hydroxylation of 4-nitrophenol and lauric acid - in the absence of NADPH and CPR. We present a proof of concept that the photoactivation of flavins is productively coupled with the direct transfer of photoinduced electrons to the P450 heme iron, achieving photobiocatalytic C-hydroxylation reactions. Photoactivation of flavins is coupled productively with the direct transfer of photoinduced electrons to P450s to achieve photobiocatalytic C-hydroxylation reactions in the absence of nicotinamide cofactors.
ISSN:1463-9262
1463-9270
DOI:10.1039/c8gc02398k