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Vitamin D


DATA No : VVD0659 INFORMANT : Sachiko Yamada

NAME : (7E)-(1R,2S,3R,20S)-2-methyl-19-nor-9,10-seco-5,7-cholestadiene-1,3,25-triol

COMMON NAME: 1a,25-dihydroxy-2a-methyl-19-nor-20-epivitamin D3 / 1a,25-dihydroxy-2a-methyl-19-nor-20-epicholecalciferol
SYMBOL:
FORMULA: C27H46O3 MOL.WT (average) : 418.652


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BIOLOGICAL ACTIVITY
Affinity for the porcine intestinal vitamin D receptor: ED50 4.0 times 10-10 M (1/4.4 less active than 1,25-(OH)2D3); HL-60 cell differentiation: ED50 7.0 times 10-11 M (50 times as active as 1,25-(OH)2D3); Intestinal calcium transport: more than twice as active as 1,25-(OH)2D3; Bone calcium mobilization: more than twice as active as 1,25-(OH)2D3. (Ref. 0355)
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CHEMICAL SYNTHESIS
A-ring synthon obtained from (-)-quinic acid was combined with Grundmann type 8-ketone by Wittig type reaction. (Ref. 0355)
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REFERENCES
[0355]
AUTHOR:Sicinski, R. R., Prahl, J. M., Smith, C. M., and DeLuca, H. F.
TITLE:New 1alpha,25-dihydroxy-19-norvitamin D3 compounds of high biological activity: synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogues PubMed ID:9804706
JOURNAL:J Med Chem.
VOL:41 PAGE : 4662-4674 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.