𝔖 Bobbio Scriptorium
✦   LIBER   ✦

1H and 13C NMR chemical shift assignments and conformational analysis for the two diastereomers of the vitamin K epoxide reductase inhibitor brodifacoum

✍ Scribed by John R. Cort; Herman Cho

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
134 KB
Volume
47
Category
Article
ISSN
0749-1581

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

DFT-GIAO1H NMR chemical shifts predictio
DFT-GIAO1H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (−)-scopolamine and (−)-hyoscyamine
✍ Marcelo A. Muñoz; Pedro Joseph-Nathan 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 179 KB 👁 1 views

## Abstract The relatively large chemical shift differences observed in the ^1^H NMR spectra of the anticholinergic drugs (−)‐scopolamine 1 and (−)‐hyoscyamine 2 measured in CDCl~3~ are explained using a combination of systematic/molecular mechanics force field (MMFF) conformational searches and ga

DFT-GIAO 1H and 13C NMR prediction of ch
DFT-GIAO 1H and 13C NMR prediction of chemical shifts for the configurational assignment of 6β-hydroxyhyoscyamine diastereoisomers
✍ Marcelo A. Muñoz; Pedro Joseph-Nathan 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 154 KB 👁 1 views

## Abstract ^1^H and ^13^C NMR chemical shift calculations using the density functional theory–gauge including/invariant atomic orbitals (DFT–GIAO) approximation at the B3LYP/6‐311G++(d,p) level of theory have been used to assign both natural diastereoisomers of 6β‐hydroxyhyoscyamine. The theoretic

Assignment of the Nonexchanging Protons
Assignment of the Nonexchanging Protons of the α-Spectrin SH3 Domain by Two- and Three- Dimensional 1H–13C Solid-State Magic-Angle Spinning NMR and Comparison of Solution and Solid-State Proton Chemical Shifts
✍ Barth-Jan van Rossum; Federica Castellani; Kristina Rehbein; Jutta Pauli; Hartmu 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 215 KB 👁 1 views

The assignment of nonexchanging protons of a small microcrystalline protein, the alpha-spectrin SH3 domain (7.2 kDa, 62 residues), was achieved by means of three-dimensional (3D) heteronuclear (1H-13C-13C) magic-angle spinning (MAS) NMR dipolar correlation spectroscopy. With the favorable combinatio