Aromatic Halogenation by Using Bifunctional Flavin Reductase-Halogenase Fusion Enzymes
نویسندگان
چکیده
منابع مشابه
Halogenase‐Inspired Oxidative Chlorination Using Flavin Photocatalysis
Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O2 as the oxidant. A photocatalytic oxidative chlorination is described based on the or...
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Vibrio harveyi luciferase and flavin reductase FRP are, together, a two-component monooxygenase couple. The reduced flavin mononucleotide (FMNH2) generated by FRP must be supplied, through either free diffusion or direct transfer, to luciferase as a substrate. In contrast, single-component bifunctional monooxygenases each contains a bound flavin cofactor and does not require any flavin addition...
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In recent years many efforts have been made aiming to define the conditions of the reaction of substitution which lead to inversion of configuration (Walden inversion). The investigations in this direction of Polanyi et al.,’ of Olson,2 of Hughes, Ingold, et aL3 are most outstanding. Polanyi et al. and Olson came to the conclusion that all reactions of substitution by a negative group or ion ar...
متن کاملFlavin redox chemistry precedes substrate chlorination during the reaction of the flavin-dependent halogenase RebH.
The flavin-dependent halogenase RebH catalyzes chlorination at the C7 position of tryptophan as the initial step in the biosynthesis of the chemotherapeutic agent rebeccamycin. The reaction requires reduced FADH(2) (provided by a partner flavin reductase), chloride ion, and oxygen as cosubstrates. Given the similarity of its sequence to those of flavoprotein monooxygenases and their common cosu...
متن کاملExtending the biocatalytic scope of regiocomplementary flavin-dependent halogenase enzymes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc00913h
Flavin-dependent halogenases are potentially valuable biocatalysts for the regioselective halogenation of aromatic compounds. These enzymes, utilising benign inorganic halides, offer potential advantages over traditional non-enzymatic halogenation chemistry that often lacks regiocontrol and requires deleterious reagents. Here we extend the biocatalytic repertoire of the tryptophan halogenases, ...
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ژورنال
عنوان ژورنال: ChemBioChem
سال: 2017
ISSN: 1439-4227
DOI: 10.1002/cbic.201700391