Vitamin D in solution: Conformations of vitamin D3, 1α,25-dihydroxyvitamin D3, and dihydrotachysterol3

Richard M. Wing, William H. Okamura, Marcel R. Pirio, Steven M Sine, Anthony W. Norman

Research output: Contribution to journalArticle

Abstract

Solution conformations of the A and seco B rings of vitamin D3, 1α,25-dihydroxyvitamin D3, 1α-hydroxyvitamin D 3, and dihydrotachysterol3 have been established by high resolution, 300-megahertz proton magnetic resonance spectroscopy. The A ring of these steroids is dynamically equilibrated between two chair conformers. For vitamin D3, 1α-hydroxyvitamin D3, and 1α,25-dihydroxyvitamin D3 the relative proportions of the two conformers are 1:1, whereas dihydrotachysterol3 exists principally as only one conformer. Thus, the substituent groups on the A ring may be either equatorially or axially oriented, and suggests a refinement of the existing topological model for vitamin D hormonal activity.

Original languageEnglish (US)
Pages (from-to)939-940
Number of pages2
JournalScience
Volume186
Issue number4167
StatePublished - 1974
Externally publishedYes

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    Wing, R. M., Okamura, W. H., Pirio, M. R., Sine, S. M., & Norman, A. W. (1974). Vitamin D in solution: Conformations of vitamin D3, 1α,25-dihydroxyvitamin D3, and dihydrotachysterol3. Science, 186(4167), 939-940.