Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases

Braddock A. Sandoval, Andrew J. Meichan, Todd K. Hyster

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

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 α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.

Original languageEnglish (US)
Pages (from-to)11313-11316
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number33
DOIs
StatePublished - Aug 23 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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