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1 H and 13 C NMR chemical shift assignments and conformational analysis for the two diastereomers of the vitamin K epoxide reductase inhibitor brodifacoum
Author(s) -
Cort John R.,
Cho Herman
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2475
Subject(s) - diastereomer , chemistry , chemical shift , stereochemistry , heteronuclear molecule , nmr spectra database , nuclear magnetic resonance spectroscopy , proton nmr , spectral line , physics , astronomy
Proton and 13 C NMR chemical shifts and 1 H 1 H scalar couplings for the two diastereomers of the potent vitamin K epoxide reductase (VKOR) inhibitor brodifacoum have been determined at 293 K from acetone solutions containing both diastereomers. To facilitate difficult assignments, homo‐ and heteronuclear correlation spectra were acquired at 750 and 900 MHz over 268–303 K temperature range. Conformations of both diastereomers inferred from the scalar couplings and 1‐D NOE measurements reveal that one diastereomer ( SS/RR ) adopts a strained geometry in the cyclohexene ring system of the tetralin group. The NMR spectra also show evidence of line broadening due to conformational exchange at room temperature for the SR/RS diastereomer. These assignments and conformational analyses may be useful in studies of biomolecular interactions of brodifacoum with target proteins such as VKOR and in source determination of brodifacoum. Copyright © 2009 John Wiley & Sons, Ltd.