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Vitamin D


DATA No : VVD0349 INFORMANT : Sachiko Yamada

NAME : (5Z,7E,22E)-(1S,3R,24S)-24-fluoro-9,10-seco-5,7,10(19),22-ergostatetraene-1,3,25-triol

COMMON NAME: (24S)-24-fluoro-1a,25-dihydroxyvitamin D2 / (24S)-24-fluoro-1a,25-dihydroxyergocalciferol
SYMBOL: 24-epi-24-F-1a,25-(OH)2D2
FORMULA: C28H43FO3 MOL.WT (average) : 446.638


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BIOLOGICAL ACTIVITY
Chick intestinal VDR binding : 10. HL-60 cell antiproliferative activity : 100. HL-60 cell differentiation (phagocytosis) : 100. HL-60 cell differentiation (NBT reduction) : 100. DBP binding : 10. (The results for 1a,25-dihydroxyvitamin D3 are normalized to 100.) The analogue showed weak response in both in vivo and in vitro bone calcium mobilization test. The analogue had weak activity to stimulate intestinal calcium transport. (Ref. 0250)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D +1.6 deg (c = 0.03 in EtOH) (Ref. 0249)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:(EtOH) lmax (nm) (emax) 264 (18900) (Ref. 0249)

IR SPECTRA:(CHCl3) 3420, 1576, 1541, 1047 cm-1 (Ref. 0249)

NMR SPECTRA:1H-NMR (d, CDCl3, 400MHz) 0.57 (3H, s), 1.05 (3H, d, J = 6.7 Hz), 1.23 (3H, s), 1.26 (3H, s), 1.43 (3H, d, J = 22.8 Hz), 2.32 (1H, dd, J = 6.4, 13.9 Hz), 2.60 (1H, dd, J = 3.1, 13.9 Hz), 2.83 (1H, dd, J = 3.8, 12.1 Hz), 4.19-4.26 (1H, m), 4.42-4.45 (1H, m), 5.00 (1H, s), 5.32 (1H, t, J = 1.6 Hz), 5.54 (1H, t, J = 16.0 Hz ), 5.61 (1H, dd, J = 8.3, 16.0 Hz), 6.01 (1H, d, J = 11.3 Hz), 6.38 (1H, d, J = 11.3 Hz) (Ref. 0249)

MASS SPECTRA:m/z 426 (M+-HF), 408 (M+-HF-H2O), 390 (M+-HF-2H2O), 372 (M+-HF-3H2O) (Ref. 0249)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC : Lichrosorb RP-18, 10 times 250 mm ; mobile phase, H2O-MeCN (55 : 45) ; 4 ml/min ; tR = 18.2 min (Ref. 0249)
SOURCE

CHEMICAL SYNTHESIS
Starting with 1a,3b-bis[(tert-butyldimethylsilyl)oxy]-24-norchol-5,7-dien-23-al, a mixture of 24-Fluoro-1a,25-dihydroxyvitamin D2 and its 24-Epimer was obteined in 3 % overall yield. (Ref. 0249)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0249]
AUTHOR:Hayashi, T.; Ojima, K.; Konno, K.; Manaka, A.; Yamaguchi, K.; Yamada, S.; Takayama, H.
TITLE:A New Synthesis of 24-Fluoro-1a,25-dihydroxyvitamin D2 and its 24-Epimer, and Determination of the C-24 Configuration.
JOURNAL:Chem. Pharm. Bull.
VOL:40 PAGE : 2932 -2936 (1992)
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[0250]
AUTHOR:Imae, Y., Manaka, A., Yoshida, N., Ishimi, Y., Shinki, T., Abe, E., Suda, T., Konno, K., Takayama, H., and Yamada, S.
TITLE:Biological activities of 24-fluoro-1 alpha,25-dihydroxyvitamin D-2 and its 24-epimer PubMed ID:8049243
JOURNAL:Biochim Biophys Acta.
VOL:1213 PAGE : 302-308 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.