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- Title
Chiroptical Study and Absolute Configuration of (−)- O-DMA Produced From Daidzein Metabolism.
- Authors
Kim, Mihyang; Han, Jaehong
- Abstract
ABSTRACT To elucidate the hitherto unknown absolute configuration of (−)- O-desmethylangolensin ((−)- O-DMA), an intestinal bacterial metabolite produced from daidzein, chiroptical study, including specific optical rotation and electronic circular dichroism (ECD), of ( R)- O-DMA was carried out by Time-Dependent Density Functional Theory (TD-DFT) calculations. hydrogen bonding between 2'-OH and carbonyl oxygen at 1-C of O-DMA was a governing factor for O-DMA to form the stable conformations. Total energy values of four possible conformers were calculated in the framework of DFT using the B3LYP exchange correlation functional at the 6-31++G basis set level. The theoretical specific rotation and ECD spectra of all conformers in ethanol were obtained by TD-DFT calculation using B3LYP functional at the 6-311++G basis set level, and compared to the experimental data. Chiroptical properties of ( R)- O-DMA showed a good agreement with the biological (−)- O-DMA. Therefore, the stereospecific biosynthetic pathway of (−)- O-DMA was proposed as daidzein → ( R)-dihydrodaidzein ↔ ( S)-dihydrodaizein → ( R)- O-DMA. Chirality 26:74-77, 2014. © 2014 Wiley Periodicals, Inc.
- Subjects
DAIDZEIN; OPTICAL rotation; CIRCULAR dichroism; HYDROGEN bonding; TIME-dependent density functional theory; CONFORMERS (Chemistry)
- Publication
Chirality, 2014, Vol 26, Issue 9, p74
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.22295