Synthesis of 2β-substituted-14-epi-previtamin D3 and testing of its genomic activity

Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Ken ichiro Takagi, Eiji Ochiai, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


2β-Substituted analogs of 14-epi-previtamin D3 were synthesized for the first time by the thermal isomerization of the corresponding 14-epi-vitamin D3 that were available using coupling reaction between the A-ring phosphine oxide derived from a chiral epoxide and CD-ring cis-hydrindanone. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the new analogs were found to be less active, 0.01-0.18% of VDR binding affinity compared with the natural hormone and EC50 1.0-9.1nM for transactivation activity, than 14-epi-previtamin D3 with 0.5% (VDR) and EC50 0.46nM, respectively.

Original languageEnglish
Pages (from-to)20-24
Number of pages5
JournalJournal of Steroid Biochemistry and Molecular Biology
Issue number1-2
Publication statusPublished - Jul 2010
Externally publishedYes


  • 14-epi-Previtamin D
  • Osteocalcin
  • Vitamin D
  • Vitamin D receptor

ASJC Scopus subject areas

  • Endocrinology, Diabetes and Metabolism
  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Endocrinology
  • Clinical Biochemistry
  • Cell Biology


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