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

doi:10.1021/jo010375i

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 journal › Article › peer-review

98 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 language	English
Pages (from-to)	8760-8771
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	66
Issue number	26
DOIs	https://doi.org/10.1021/jo010375i
Publication status	Published - 2001 Dec 28
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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 = "Y. 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",

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doi = "10.1021/jo010375i",

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

AU - Suhara, Y.

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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

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

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ASJC Scopus subject areas

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