Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors

Y. Suhara, K. I. Nihei, M. Kurihara, A. Kittaka, K. Yamaguchi, T. Fujishima, K. Konno, N. Miyata, H. Takayama

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

Novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues with 2α-alkyl and 2α-hydroxyalkyl groups were systematically synthesized from D-xylose. Their conformation on binding to the ligand binding domain (LBD) of the vitamin D receptor was analyzed. It has been found that the 2α-hydroxypropyl group best fits the cavity of the LBD, and the binding activity is three times higher than that for the natural hormone.

Original languageEnglish
Pages (from-to)8760-8771
Number of pages12
JournalJournal of Organic Chemistry
Volume66
Issue number26
DOIs
Publication statusPublished - 2001 Dec 28

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Suhara, Y., Nihei, K. I., Kurihara, M., Kittaka, A., Yamaguchi, K., Fujishima, T., Konno, K., Miyata, N., & Takayama, H. (2001). Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors. Journal of Organic Chemistry, 66(26), 8760-8771. https://doi.org/10.1021/jo010375i