Abstract
The three-step conversion of vitamin D analogs to 6-oxo-3,5-cyclovitamin D derivatives followed by reduction with a tritide or deuteride reagent and subsequent cycloreversion gives 6-tritio(deutero)vitamin D derivatives and corresponding 5,6-trans-analogs. The method is general and affords the 6-labeled-vitamin D analogs in ≈20% overall yield.
Keywords: calcium, labeled vitamin D, calciferol, bone
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Selected References
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- Esvelt R. P., Schnoes H. K., DeLuca H. F. Isolation and characterization of 1 alpha-hydroxy-23-carboxytetranorvitamin D: a major metabolite of 1,25-dihydroxyvitamin D3. Biochemistry. 1979 Sep 4;18(18):3977–3983. doi: 10.1021/bi00585a021. [DOI] [PubMed] [Google Scholar]
- Kumar R., Harnden D., DeLuca H. F. Metabolism of 1,25-dihydroxyvitamin D3: evidence for side-chain oxidation. Biochemistry. 1976 Jun 1;15(11):2420–2423. doi: 10.1021/bi00656a027. [DOI] [PubMed] [Google Scholar]
- Napoli J. L., Fivizzani M. A., Hamstra A. J., Schnoes H. K., DeLuca H. F. Synthesis of 25-hydroxy[26,27-3h]vitamin D3 with high specific activity. Anal Biochem. 1979 Jul 15;96(2):481–488. doi: 10.1016/0003-2697(79)90610-9. [DOI] [PubMed] [Google Scholar]
- Napoli J. L., Mellon W. S., Fivizzani M. A., Schnoes H. K., DeLuca H. F. Direct chemical synthesis of 1 alpha,25-dihydroxy[26,27-3H]vitamin D3 with high specific activity: its use in receptor studies. Biochemistry. 1980 May 27;19(11):2515–2521. doi: 10.1021/bi00552a033. [DOI] [PubMed] [Google Scholar]
- Schnoes H. K., DeLuca H. F. Recent progress in vitamin D metabolism and the chemistry of vitamin D metabolites. Fed Proc. 1980 Aug;39(10):2723–2729. [PubMed] [Google Scholar]
- Sheves M., Mazur Y. Letter: The vitamin D-3,5-cyclovitamin D rearrangement. J Am Chem Soc. 1975 Oct 15;97(21):6249–6250. doi: 10.1021/ja00854a053. [DOI] [PubMed] [Google Scholar]
- Wichmann J. K., DeLuca H. F., Schnoes H. K., Horst R. L., Shepard R. M., Jorgensen N. A. 25-Hydroxyvitamin D3 26,23-lactone: a new in vivo metabolite of vitamin D. Biochemistry. 1979 Oct 30;18(22):4775–4780. doi: 10.1021/bi00589a002. [DOI] [PubMed] [Google Scholar]
