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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Calcitriol
Cholecalciferol
Vitamin D
Conformations
Magnetic resonance spectroscopy
Hydroxycholecalciferols
Steroids
Nuclear magnetic resonance

ASJC Scopus subject areas

  • General

Cite this

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.

Vitamin D in solution : Conformations of vitamin D3, 1α,25-dihydroxyvitamin D3, and dihydrotachysterol3. / Wing, Richard M.; Okamura, William H.; Pirio, Marcel R.; Sine, Steven M; Norman, Anthony W.

In: Science, Vol. 186, No. 4167, 1974, p. 939-940.

Research output: Contribution to journalArticle

Wing, RM, Okamura, WH, Pirio, MR, Sine, SM & Norman, AW 1974, 'Vitamin D in solution: Conformations of vitamin D3, 1α,25-dihydroxyvitamin D3, and dihydrotachysterol3', Science, vol. 186, no. 4167, pp. 939-940.
Wing, Richard M. ; Okamura, William H. ; Pirio, Marcel R. ; Sine, Steven M ; Norman, Anthony W. / Vitamin D in solution : Conformations of vitamin D3, 1α,25-dihydroxyvitamin D3, and dihydrotachysterol3. In: Science. 1974 ; Vol. 186, No. 4167. pp. 939-940.
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