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Photochemically Driven Biocatalysis of Halogenases for the Green Production of Chlorinated Compounds
Author(s) -
Schroeder Lea,
Frese Marcel,
Müller Caroline,
Sewald Norbert,
Kottke Tilman
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800280
Subject(s) - flavin group , biocatalysis , chemistry , cofactor , regioselectivity , halogenation , indole test , combinatorial chemistry , photochemistry , organic chemistry , enzyme , reaction mechanism , catalysis
Flavin‐dependent tryptophan halogenases provide a regioselective access to chlorinated and brominated indole derivatives under mild conditions. Application of the halogenase requires a regeneration system for the reduced flavin cofactor FADH 2 , which is usually achieved by enzymatic or chemical reactions. We employed the halogenase PyrH from Streptomyces rugosporus as a model system to establish a photochemical approach by using blue light and a reductant for regeneration of FADH 2 . In contrast to previous light‐driven biocatalysis using flavin, the conversion of enzyme‐bound flavin in our approach suppresses futile cycles, in which the free flavin reacts with oxygen under generation of H 2 O 2 . Within 25 h, 70 % of 0.5 m m tryptophan was converted regioselectively to 5‐chlorotryptophan. Our regeneration system paves the way for production of chlorinated compounds by applying only light, halide salt, air, and a cheap sacrificial electron donor in aqueous solution.