The synthesis and bone resorbing activity of (25R)- and (25S)-26-hydroxycholecalciferol (26-OH-D 3)

The synthesis of C-25 epimers of 26-hydroxycholecalciferol (26-OH-D 3) (III)—the so far unknown 25-deoxy analogue of the metabolite 25,26(OH) 2D 3—is described. (25R)- or (25S)-26-hydroxycholesterol 3,26-diacetate (I) was converted into the corresponding mixture of 5,7- and 4,6-diene, saponified and...

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Published inJournal of steroid biochemistry Vol. 9; no. 12; pp. 1179 - 1182
Main Authors Redel, J., Rebut-Bonneton, C., Delbarre, F.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.01.1978
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Summary:The synthesis of C-25 epimers of 26-hydroxycholecalciferol (26-OH-D 3) (III)—the so far unknown 25-deoxy analogue of the metabolite 25,26(OH) 2D 3—is described. (25R)- or (25S)-26-hydroxycholesterol 3,26-diacetate (I) was converted into the corresponding mixture of 5,7- and 4,6-diene, saponified and then directly irradiated with U.V. light. The obtained precholecalci ferol analog was isomerized thermally to III and separated from the 4,6-diene on Sephadex LH 20. Tested for bone resorption in organ cultures from mouse calvaria in vitro, (25R)-26-OH-D 3 is less effective than 25,26(OH) 2D 3, whereas (25S)-26-OH-D 3 is inactive. By the in vivo/ in vitro method, (25R)and (25S)-26-OH-D 3 are ineffective, while 25R,26- and 25S,26(OH) 2D 3 are moderately osteolytic.
ISSN:0022-4731
DOI:10.1016/0022-4731(78)90009-2