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Synthesis of 25-hydroxy-[26,27-3H]vitamin D2, 1,25-dihydroxy-[26,27-3H]vitamin D2 and their (24R)-epimers

✍ Scribed by Rafal R. Sicinski; Yoko Tanaka; Mary Phelps; Heinrich K. Schnoes; Hector F. DeLuca

Publisher: Elsevier Science
Year: 1987
Tongue: English
Weight: 573 KB
Volume: 161
Category: Article
ISSN: 0003-2697
DOI: 10.1016/0003-2697(87)90657-9

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✦ Synopsis

Synthesis of a C-24-epimeric mixture of 25-hydroxy-[26,27-3H]vitamin D2 and a C-24-epimeric mixture of 1,25-dihydroxy-[26,27-'HIvitamin D2 by the Grignard reaction of the corresponding 25-keto-27-nor-vitamin D2 and lo-acetoxy-25keto-27-nor-vitamin D3 with tritiated methyl magnesium bromide is described. Separation of epimers by high-performance liquid chromatography afforded pure radiolabeled vitamins of high specific activity (80 Ci/mmol). The identities and radiochemical purities of 25-hydroxy-[26,27-3H[vitamin D2 and 1,25-dihydroxy-[26,27-3H]vitamin D2 were established by cochromatography with synthetic 25hydroxyvitamin Dz or 1,25-dihydroxyvitamin D 2. Biological activity of 25-hydroxy-[26,27-3H]vitamin D2 was demonstrated by its binding to the rat plasma binding protein for vitamin D compounds, and by its in vitro conversion to l,25-dihydroxy-[26,27-3H]vitamin D2 by kidney homogenate prepared from vitamin D-deficient chickens. The biological activity of 1 ,25-dihydroxy-[26,27-3H]vitamin D2 was demonstrated by its binding to the chick intestinal receptor for 1,25-dihydroxyvitamin D3. 0 1987 Academic FWSS. hc.

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