Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate
- Authors
- Kim, Mihyang; Marsh, E. Neil G.; Kim, Soo-Un; Han, Jaehong
- Issue Date
- Jul-2010
- Publisher
- AMER CHEMICAL SOC
- Citation
- BIOCHEMISTRY, v.49, no.26, pp 5582 - 5587
- Pages
- 6
- Journal Title
- BIOCHEMISTRY
- Volume
- 49
- Number
- 26
- Start Page
- 5582
- End Page
- 5587
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/22333
- DOI
- 10.1021/bi100465y
- ISSN
- 0006-2960
1520-4995
- Abstract
- 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 H-1 NMR and H-2 NMR spectroscopy, and the product was identified as (2,3,4(alpha)-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.
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Collections - College of Biotechnology & Natural Resource > ETC > 1. Journal Articles
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