A 13C-NMR. Study of cis-trans isomeric vitamins A, carotenoids and related compounds.

作者: Gerhard Englert

DOI: 10.1002/HLCA.19750580817

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摘要: The 1H-decoupled 13C-NMR. spectra of 35 all-trans, 17 mono-cis vitamin A compounds (acetates, alcohols, aldehydes, acids and esters) one 11, 13-di-cis compound (11, retinol) are reported. Included in this investigation desmethyl-, desmethylethyl, aryl-vitamin analogues others as well 30 reference smaller molecular weight. Furthermore, the 23 β-apo- other carotenoids were studied. complete assignment signals all 106 to specific carbon atoms was achieved by extensive application lanthanide shift reagents, mainly Yb(dpm)3, CW-offset selective 1H-decoupling experiments, comparison shifts related compounds, three cases utilization specifically deuteriated 12-D2-retinol retinyl acetate, 15, 15′-D2-β-carotene). chemical differences between cis- trans-vitamin applicability reagents for discussed.

参考文章(15)
U. Schwieter, G. Englert, N. Rigassi, W. Vetter, Physical organic methods in carotenoid research Pure and Applied Chemistry. ,vol. 20, pp. 365- 420 ,(1969) , 10.1351/PAC196920040365
Ernest Wenkert, David W. Cochran, Edward W. Hagaman, R. Burton Lewis, F. M. Schell, Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. VII. Carbon-13 nuclear magnetic resonance spectroscopy with the aid of a paramagnetic shift agent Journal of the American Chemical Society. ,vol. 93, pp. 6271- 6273 ,(1971) , 10.1021/JA00752A049
J. G. Batchelor, J. H. Prestegard, R. J. Cushley, S. R. Lipsky, Electric field effects in the carbon-13 nuclear magnetic resonance spectra of unsaturated fatty acids. Potential tool for conformational analysis Journal of the American Chemical Society. ,vol. 95, pp. 6358- 6364 ,(1973) , 10.1021/JA00800A032
Barry Honig, Arieh Warshel, Martin Karplus, Theoretical studies of the visual chromophore Accounts of Chemical Research. ,vol. 8, pp. 92- 100 ,(1975) , 10.1021/AR50087A003
B. Vernon. Cheney, Magnetic deshielding of protons due to intramolecular steric interactions with proximate hydrogens Journal of the American Chemical Society. ,vol. 90, pp. 5386- 5390 ,(1968) , 10.1021/JA01022A009
Robert III Rowan, Brian D. Sykes, A 1-H nuclear magnetic resonance determination of the conformations of the polyene chain portions of 9-cis- and 13-cis-retinal in solution. Journal of the American Chemical Society. ,vol. 97, pp. 1023- 1027 ,(1975) , 10.1021/JA00838A013
Otto A. Gansow, Paul A. Loeffler, Raymond E. Davis, M. R. Willcott, Robert E. Lenkinski, Interpretation of the pseudocontact model for nuclear magnetic resonance shift reagents. IV. Evaluation of lanthanide-induced carbon-13 contact vs. pseudocontact nuclear magnetic resonance shifts Journal of the American Chemical Society. ,vol. 95, pp. 3389- 3390 ,(1973) , 10.1021/JA00791A056
Yoshio Inoue, Akio Takahashi, Yasuo Tokitô, Riichirô Chûjô, Yasuhiro Miyoshi, Carbon-13 NMR spectra of retinal1 and its related compounds Organic Magnetic Resonance. ,vol. 6, pp. 487- 491 ,(1974) , 10.1002/MRC.1270060907
M. Jautelat, J. B. Grutzner, J. D. Roberts, Natural-Abundance 13C Nuclear Magnetic Resonance Spectra of Terpenes and Carotenes Proceedings of the National Academy of Sciences of the United States of America. ,vol. 65, pp. 288- 292 ,(1970) , 10.1073/PNAS.65.2.288
Robert III Rowan, Brian D. Sykes, A carbon-13 nuclear magnetic resonance study of the visual chromophores and model compounds. Journal of the American Chemical Society. ,vol. 96, pp. 7000- 7008 ,(1974) , 10.1021/JA00829A031