Flavin-Dependent Halogenases fromXanthomonas campestrispv. campestris B100 Prefer Bromination over Chlorination
نویسندگان
چکیده
منابع مشابه
Chlorination by a long-lived intermediate in the mechanism of flavin-dependent halogenases.
The flavin-dependent halogenase RebH catalyzes the formation of 7-chlorotryptophan as the initial step in the biosynthesis of antitumor agent rebeccamycin. The reaction of FADH2, Cl-, and O2 in the active site generates the powerful oxidant HOCl, which was presumed to carry out the chlorination reaction. Herein, we demonstrate the formation of a long-lived chlorinating intermediate (t1/2 = 63 h...
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 کاملHalogenase‐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...
متن کاملA Structure‐Guided Switch in the Regioselectivity of a Tryptophan Halogenase
Flavin-dependent halogenases are potentially useful biocatalysts for the regioselective halogenation of aromatic compounds. Haloaromatic compounds can be utilised in the synthesis and biosynthesis of pharmaceuticals and other valuable products. Here we report the first X-ray crystal structure of a tryptophan 6-halogenase (SttH), which enabled key residues that contribute to the regioselectivity...
متن کاملRegioselective copper-catalyzed chlorination and bromination of arenes with O(2) as the oxidant.
Electron-rich aromatic C-H bonds undergo regioselective chlorination and bromination in the presence of CuX(2), LiX (X = Cl, Br) and molecular oxygen. Preliminary mechanistic insights suggest that the bromination and chlorination reactions proceed by different pathways.
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ژورنال
عنوان ژورنال: Advanced Synthesis & Catalysis
سال: 2019
ISSN: 1615-4150
DOI: 10.1002/adsc.201801591