Conformations of Flavan-3-ols in Water: Analysis Using Density Functional Theory.

Content Provider	Semantic Scholar
Author	Hayashi, Nobuyuki Ujihara, Tomomi
Copyright Year	2017
Abstract	To elucidate the conformations and their relative stabilities of flavan-3-ols in water, the optimized structures and energies were calculated by density functional theory, in which M06-2X, ωB97X-D, B3LYP, and CAM-B3LYP were examined as exchange-correlation functionals. The results were evaluated by comparing calculated spin-spin coupling constants of vicinal protons with the corresponding values observed in experimental 1H NMR spectra in D2O. The M06-2X and ωB97X-D results showed good agreement with the experimental NMR data and revealed that the B-ring (pseudoequatorial)/3-O (pseudoaxial) conformers were more stable [5.4-8.7 kJ/mol (1.3-2.1 kcal/mol)] than the B-ring (pseudoaxial)/3-O (pseudoequatorial) conformers in the 2,3-cis-flavan-3-ols, while the B-ring (pseudoequatorial)/3-O (pseudoequatorial) conformers and the B-ring (pseudoaxial)/3-O (pseudoaxial) conformers had similar stabilities in the 2,3-trans-flavan-3-ols.
Starting Page	319
Ending Page	327
Page Count	9
File Format	PDF HTM / HTML
Alternate Webpage(s)	https://s3-eu-west-1.amazonaws.com/pstorage-acs-6854636/7428349/np6b00704_si_001.pdf
PubMed reference number	28124903v1
Alternate Webpage(s)	https://doi.org/10.1021/acs.jnatprod.6b00704
DOI	10.1021/acs.jnatprod.6b00704
Journal	Journal of natural products
Volume Number	80
Issue Number	2
Language	English
Access Restriction	Open
Subject Keyword	DUOXA1 gene Energy, Physics Protons chorioallantoic membrane kilocalorie kilojoule (kJ)
Content Type	Text
Resource Type	Article