1 alpha, 25-difluorovitamin D3: an inert vitamin D analog |
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Authors: | H E Paaren M A Fivizzani H K Schnoes H F De Luca |
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Affiliation: | Department of Biochemistry, College of Agricultural and Life Sciences, University of Wisconsin-Madison, Madison, Wisconsin 53706 U.S.A. |
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Abstract: | 1α,25-Difluorovitamin D3 has been synthesized by reacting 1,25-dihydroxyvitamin D3-3-acetate with diethylaminosulfurtrifluoride followed by hydrolysis. Retention of configuration of the fluoro group in this reaction was demonstrated by physical studies using 1α-fluoro and 1β-fluorovitamin D3 models. The 1,25-difluorovitamin D3 compound possessed no vitamin D-like activity demonstrating the importance of 1α- and 25-hydroxylations of vitamin D for activity. However, 1,25-difluorovitamin D3 had no anti-25-hydroxylation activity and no antivitamin D activity. Since 25-fluorovitamin D3 has anti-25-hydroxylase activity, it appears the introduction of a fluoro group on the 1 position diminishes interaction of the vitamin D molecule with the 25-hydroxylase system. |
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Keywords: | To whom correspondence should be addressed. |
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