1␣,25(OH) 2 D 3 is an important negative regulator of parathyroid hormone (PTH) gene transcription. In parathyroid cells, as in other target tissues, 1␣,25(OH) 2 D 3 is degraded by side chain oxidation by the inducible 24-hydroxylase. We have previously shown that one metabolite of this pathway, 1␣,
(25 S)-1α, 25, 26-Trihydroxycholecalciferol, a New Vitamin D3 Metabolite: Synthesis and Absolute Stereochemistry at C(25)
✍ Scribed by John J. Partridge; Shian-Jan Shiuey; Naresh K. Chadha; Enrico G. Baggiolini; Bernard M. Hennessy; Milan R. Uskoković; Joseph L. Napoli; Timothy A. Reinhardt; Ron L. Horst
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- German
- Weight
- 189 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The 1α, 25, 26‐trihydroxy metabolite of vitamin D~3~, isolated from bovine serum, was shown to possess the (25 S)‐configuration by HPLC. comparison of the 1, 3, 26‐triacetate derivative with authentic (25 R)‐ and (25 S)‐samples. The convergent synthesis of (25 R)‐1α, 25, 26‐ and (25 S)‐1α, 25, 26‐trihydroxycholecalciferols (10a) and (10b) has been accomplished.
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Copper-Mediated Alkylation of Vitamin D C-Ring. Synthesis of C11-Functionalized 1α,25-Dihydroxyvitamin D3. -The functionalization of C-11 of CD-ring fragments of vitamin D3, e.g. (I), with organocopper reagents is studied. The application results in an efficient, convergent synthesis of the calcitr