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. 1974 Oct;71(10):4194–4197. doi: 10.1073/pnas.71.10.4194

Vitamin D: Concerning the Relationship Between Molecular Topology and Biological Function*

William H Okamura †, Anthony W Norman ‡, Richard M Wing †
PMCID: PMC434356  PMID: 4372612

Abstract

Structure-function relationships for vitamin D, its metabolites, and analogs are discussed with particular emphasis on the A-ring conformation. It is emphasized that the A-ring of these seco-steroids consists of a pair of rapidly equilibrating chair conformers. As a consequence, different chair conformations produce different orientations of substituent groups in the A-ring. It is proposed that the 1α-hydroxyl of 1α,25-dihydroxyvitamin D3 or its geometric equivalent in analogs must occupy the equatorial, as opposed to the axial, orientation for optimization of biological activity. This proposal is discussed in relation to existing published data on structure-function relationships and the steroid hormone model of action for the biologically active form of vitamin D. This three-dimensional topological model suggests the synthesis of other vitamin D analogs.

Keywords: conformational analysis; steroid hormone; calciferol; 1α,25-dihydroxyvitamin D3; calcium

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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