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

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

Research output: Contribution to journalArticle

91 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
Externally publishedYes

Fingerprint

Calcitriol Receptors
Calcitriol
Ligands
Xylose
Conformations
Hormones

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors. / Suhara, Yoshitomo; Nihei, K. I.; Kurihara, M.; Kittaka, A.; Yamaguchi, K.; Fujishima, T.; Konno, K.; Miyata, N.; Takayama, H.

In: Journal of Organic Chemistry, Vol. 66, No. 26, 28.12.2001, p. 8760-8771.

Research output: Contribution to journalArticle

Suhara, Y, Nihei, KI, 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, vol. 66, no. 26, pp. 8760-8771. https://doi.org/10.1021/jo010375i
Suhara, Yoshitomo ; Nihei, K. I. ; Kurihara, M. ; Kittaka, A. ; Yamaguchi, K. ; Fujishima, T. ; Konno, K. ; Miyata, N. ; Takayama, H. / Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors. In: Journal of Organic Chemistry. 2001 ; Vol. 66, No. 26. pp. 8760-8771.
@article{723984b197d340bd8ebb34c4349410ea,
title = "Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors",
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.",
author = "Yoshitomo Suhara and Nihei, {K. I.} and M. Kurihara and A. Kittaka and K. Yamaguchi and T. Fujishima and K. Konno and N. Miyata and H. Takayama",
year = "2001",
month = "12",
day = "28",
doi = "10.1021/jo010375i",
language = "English",
volume = "66",
pages = "8760--8771",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "26",

}

TY - JOUR

T1 - Efficient and versatile synthesis of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues and their docking to vitamin D receptors

AU - Suhara, Yoshitomo

AU - Nihei, K. I.

AU - Kurihara, M.

AU - Kittaka, A.

AU - Yamaguchi, K.

AU - Fujishima, T.

AU - Konno, K.

AU - Miyata, N.

AU - Takayama, H.

PY - 2001/12/28

Y1 - 2001/12/28

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0035966193&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035966193&partnerID=8YFLogxK

U2 - 10.1021/jo010375i

DO - 10.1021/jo010375i

M3 - Article

VL - 66

SP - 8760

EP - 8771

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 26

ER -