Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 561460
Title Flavoenzyme-mediated regioselective aromatic hydroxylation with coenzyme biomimetics
Author(s) Guarneri, Alice; Westphal, Adrie; Leertouwer, J.; Lunsonga, J.; Franssen, M.C.R.; Opperman, D.J.; Hollmann, F.; Berkel, W.J.H. van; Paul, C.E.
Source ChemCatChem 12 (2020)5. - ISSN 1867-3880 - p. 1368 - 1375.
DOI https://doi.org/10.1002/cctc.201902044
Department(s) Organic Chemistry
Biochemistry
VLAG
Food Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2020
Abstract Regioselective aromatic hydroxylation is desirable for the production of valuable compounds. External flavin‐containing monooxygenases activate and selectively incorporate an oxygen atom in phenolic compounds through flavin reduction by the nicotinamide adenine dinucleotide coenzyme and subsequent reaction with molecular oxygen. This study provides the proof of principle of flavoenzyme‐catalyzed selective aromatic hydroxylation with coenzyme biomimetics. The carbamoylmethyl‐substituted biomimetic in particular affords full conversion in less than two hours for the selective hydroxylation of 5 mM 3‐ and 4‐hydroxybenzoates, displaying similar rates as with NADH, achieving a 10 mM/h enzymatic conversion of the medicinal product gentisate. This biomimetic appears to generate less uncoupling of hydroxylation that typically leads to undesired hydrogen peroxide. Therefore, we show these flavoenzymes have the potential to be applied in combination with biomimetics.
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