Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 33, Pages 11313-11316Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05468
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- Princeton University
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Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for abromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reluctant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.
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