Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Journal of the American Chemical Society, 2017-08, Vol.139 (33), p.11313-11316

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2017

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• 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.