Determination of stereochemical configuration of the 24-hydroxyl group of 24,25-dihydroxyvitamin D/sub 3/ and its biological importance. [Rats]

Journal Article · Wed Jan 01 04:00:00 EST 1975 · Arch. Biochem. Biophys.; (United States)

DOI:https://doi.org/10.1016/0003-9861(75)90157-5· OSTI ID:7306902

Tanaka, Y; DeLuca, H F; Ikekawa, N; Morisaki, M; Koizumi, N

A method of clearly separating synthetic 24R,25-dihydroxyvitamin D/sub 3/ and 24S,25-dihydroxyvitamin D/sub 3/ as their Tris-trimethylsilyl ether derivatives has been devised using high pressure liquid chromatography on silica-gel columns. Using this technique, biologically prepared 24,25-dihydroxyvitamin D/sub 3/ has been shown to be entirely 24R,25-dihydroxyvitamin D/sub 3/. The 24R,25-dihydroxyvitamin D/sub 3/ is almost as active as 25-hydroxyvitamin D/sub 3/ in stimulating intestinal calcium transport, elevation of serum phosphorus and calcification of bone in rachitic rats. On the other hand, the 24S,25-dihydroxyvitamin D/sub 3/ has little or no activity in the cure of rickets in rats and the elevation of serum phosphorus of rachitic rats. It has some bone calcium mobilization activity but approaches the activity of 24R,25-dihydroxyvitamin D/sub 3/ in the stimulation of intestinal calcium transport. Both the bone calcium mobilization response and the intestinal calcium transport response to the R and S isomers is eliminated by nephrectomy, which illustrates that both isomers undergo 1-hydroxylation. The biological activity profile of the biologically generated 24,25-dihydroxyvitamin D/sub 3/ is identical to that of 24R,25-dihydroxyvitamin D/sub 3/ and not that of 24S,25-dihydroxyvitamin D/sub 3/, which supports the conclusion that the natural compound is 24R,25-dihydroxyvitamin D/sub 3/.

• Research Organization: Univ. of Wisconsin, Madison
• OSTI ID: 7306902
• Journal Information: Arch. Biochem. Biophys.; (United States), Journal Name: Arch. Biochem. Biophys.; (United States) Vol. 170; ISSN ABBIA
• Country of Publication: United States
• Language: English

Related Subjects

550200 -- Biochemistry
550500* -- Metabolism
59 BASIC BIOLOGICAL SCIENCES
ALKALINE EARTH METALS
ANIMALS
BODY
CALCIUM
CHOLECALCIFEROL
CHROMATOGRAPHY
DIFFUSION
DIGESTIVE SYSTEM
DISEASES
ELEMENTS
GASTROINTESTINAL TRACT
HYDROXYL RADICALS
INTESTINES
MAMMALS
METABOLISM
METALS
MOLECULAR STRUCTURE
NONMETALS
ORGANS
PHOSPHORUS
RADICALS
RATS
RICKETS
RODENTS
SEPARATION PROCESSES
SKELETAL DISEASES
STEREOCHEMISTRY
VERTEBRATES
VITAMIN D
VITAMINS