Conformational analysis of six-membered rings in solution: ring puckering coordinates derived from vicinal NMR proton-proton coupling constants

1993 ◽  
Vol 115 (4) ◽  
pp. 1460-1468 ◽  
Author(s):  
C. A. G. Haasnoot
Keyword(s):  
Conformational Analysis ◽  
Coupling Constants ◽  
Proton Proton ◽  
Proton Coupling ◽  
Ring Puckering

Conformational analysis of the .alpha.-L-arabinofuranosides present in wheat arabinoxylans from proton-proton coupling constants

1992 ◽  
Vol 114 (10) ◽  
pp. 3710-3714 ◽  
Author(s):  
R. A. Hoffmann ◽  
J. Van Wijk ◽  
B. R. Leeflang ◽  
J. P. Kamerling ◽  
C. Altona ◽  
...  
Keyword(s):  
Conformational Analysis ◽  
Coupling Constants ◽  
Proton Proton ◽  
Proton Coupling

The conformational analysis of leukotriene D4 in aqueous solution based on high-field nuclear magnetic resonance measurements

1984 ◽  
Vol 62 (8) ◽  
pp. 1640-1645 ◽  
Author(s):  
Makiko Sugiura ◽  
Helmut Beierbeck ◽  
George Kotovych ◽  
Patrice C. Bélanger
Keyword(s):  
Conformational Analysis ◽  
Nuclear Overhauser Effect ◽  
Relaxation Times ◽  
Coupling Constants ◽  
Leukotriene D4 ◽  
Proton Proton ◽  
Proton Coupling ◽  
Overhauser Effect ◽  
Vicinal Proton ◽  
Nuclear Overhauser

The conformational analysis of LTD4 in D2O was carried out based on the analysis of vicinal proton–proton coupling constants, nonselective proton longitudinal relaxation times, and nuclear Overhauser effect data. The H6—C6 to C12 region of the molecule is transoid, the predominant rotamer about C5—C6 is gauche, and two rotamers can be used to describe the rotation about C12—C13. There are three rotamers that can be used to describe the rotation about the C21—C22 bond of cysteine. Finally, chelation between an Yb3+, shift reagents and LTD4 was not observed.

Conformational analysis and complete assignment of the proton and carbon NMR spectra of ouabain and ouabagenin

1990 ◽  
Vol 68 (8) ◽  
pp. 1263-1270 ◽  
Author(s):  
Deane D. McIntyre ◽  
Markus W. Germann ◽  
Hans J. Vogel
Keyword(s):  
Conformational Analysis ◽  
Molecular Mechanics ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
X Ray Diffraction ◽  
Proton Proton ◽  
Proton Coupling ◽  
Nmr Techniques ◽  
Phase Sensitive ◽  
C Nmr

The 1H and 13C NMR spectra of the cardenolide ouabain and its aglycon ouabagenin have been completely assigned by two-dimensional NMR techniques, including phase-sensitive COSY and carbon–proton correlation (HETCOR, HMQC, and COLOC) spectra. The major conformer of these two compounds in solution is all-chair as determined from proton–proton coupling constants and is similar to that in the crystal lattice as previously determined by X-ray diffraction. The conformations of the A and D rings of ouabain in water are somewhat different than in DMSO/CDCl3 (2:1). At lower temperatures (−20 °C) signals from two conformers in slow exchange were readily observed in the 13C spectra, with an approximate ratio of 1:7. Molecular mechanics and dynamics calculations indicate that the conformational process responsible for this involves a chair/twist-boat interconversion of the A ring, with the all-chair conformer highly preferred. Keywords: ouabain, conformational analysis, 2-D NMR, molecular mechanics, molecular dynamics.

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