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Journal of Lipid Research, Vol 37, 1529-1555, Copyright © 1996 by Lipid Research, Inc.
WK Wilson, RM Sumpter, JJ Warren, PS Rogers, B Ruan and GJ Schroepfer Jr
Complete 1H and 13C nuclear magnetic resonance (NMR) signal assignments
have been established for 5 alpha-cholestan-3 beta-ol, 22 unsaturated C27
sterols, and their acetate derivatives. Assignments were made from a
combination of 1D and 2D spectra and include stereochemical 1H assignments
for the C-22 and C-23 protons of 5 alpha-cholesta-8,24-dien- 3 beta-ol and
other delta 24 sterols with a C8 side chain. At the temperature and
concentration range described, chemical shifts were generally reproducible
to +/- 0.01 ppm in 13C spectra and +/- 0.001 ppm in 1H spectra. Except for
some overlapped or strongly coupled 1H resonances, chemical shifts are
given to these precisions, which are an order of magnitude better than for
most data given previously. Full 1H NMR data have been reported previously
for only three of the 46 compounds, and 13C data were unavailable for many,
including the previously undescribed cholesta-5,8(14)-dien-3 beta-ol. An
extensive set of 1H-1H coupling constants for the unsaturated sterols
indicated considerable conformational diversity, which was confirmed by
molecular modeling. The conformational diversity together with other
factors led to a complex pattern of 13C substituent-induced chemical shifts
(SCS) that appeared to elude any simple empirical correlations with
structure. By contrast, the 1H SCS correlated reasonably well with simple
structural features. The high precision of the SCS revealed small but
measurable effects of a double bond on 1H resonances up to 12 bonds away.
Also discussed are the utility and limitations of NMR for the
identification of unsaturated sterols, estimation of purity, and analysis
of mixtures, with an emphasis on special problems encountered at a
microgram level.
ARTICLES
Analysis of unsaturated C27 sterols by nuclear magnetic resonance spectroscopy
Department of Biochemistry and Cell Biology, Rice University, Houston, TX 77251, USA.
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