1216469-13-4Relevant articles and documents
Conversion of (3 S,4 R)-tetrahydrodaidzein to (3 S)-equol by THD reductase: Proposed mechanism involving a radical intermediate
Kim, Mihyang,Marsh, E. Neil G.,Kim, Soo-Un,Han, Jaehong
, p. 5582 - 5587 (2010)
To elucidate the mechanism of (3S)-equol biosynthesis, (2,3,4-d 3)-trans-THD was synthesized and converted to (3S)-equol by THD reductase in Eggerthella strain Julong 732. The position of the deuterium atoms in (3S)-equol was determined by 1H NMR and 2H NMR spectroscopy, and the product was identified as (2,3,4α-d 3)-(3S)-equol. All the deuterium atoms were retained, while the OH group at C-4 was replaced by a hydrogen atom with retention of configuration. To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates.