Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-3H] labelled tracers

Shoujiro Ogawa; Yuuki Adachi; Genta Kakiyama; Miki Shimada; Nariyasu Mano; Junichi Goto; Takashi Iida

doi:10.1248/cpb.58.1103

Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-³H] labelled tracers

Shoujiro Ogawa, Yuuki Adachi, Genta Kakiyama, Miki Shimada, Nariyasu Mano, Junichi Goto, Takashi Iida

大学病院

研究成果: Article › 査読

2 被引用数 (Scopus)

抄録

(22E)-3α,6α,7α,12α-Tetrahydroxy-5β-chol-22-en- 24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C₂₄ 3β,6β,7β,12β- tetrahydroxylated bile acid to the corresponding C₂₂ 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-Δ²²-5β-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.

本文言語	English
ページ（範囲）	1103-1106
ページ数	4
ジャーナル	Chemical and Pharmaceutical Bulletin
巻	58
号	8
DOI	https://doi.org/10.1248/cpb.58.1103
出版ステータス	Published - 2010 8

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

文献へのアクセス

10.1248/cpb.58.1103

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フィンガープリント「Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-<sup>3</sup>H] labelled tracers」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

Ogawa, S., Adachi, Y., Kakiyama, G., Shimada, M., Mano, N., Goto, J., & Iida, T. (2010). Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-³H] labelled tracers. Chemical and Pharmaceutical Bulletin, 58(8), 1103-1106. https://doi.org/10.1248/cpb.58.1103

Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine : Precursors of the [22,23-³H] labelled tracers. / Ogawa, Shoujiro; Adachi, Yuuki; Kakiyama, Genta; Shimada, Miki; Mano, Nariyasu; Goto, Junichi; Iida, Takashi.

In: Chemical and Pharmaceutical Bulletin, Vol. 58, No. 8, 08.2010, p. 1103-1106.

研究成果: Article › 査読

Ogawa, S, Adachi, Y, Kakiyama, G, Shimada, M, Mano, N, Goto, J & Iida, T 2010, 'Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: Precursors of the [22,23-³H] labelled tracers', Chemical and Pharmaceutical Bulletin, vol. 58, no. 8, pp. 1103-1106. https://doi.org/10.1248/cpb.58.1103

Ogawa, Shoujiro ; Adachi, Yuuki ; Kakiyama, Genta ; Shimada, Miki ; Mano, Nariyasu ; Goto, Junichi ; Iida, Takashi. / Chemical synthesis of (22E)-3α,6α,7α,12α- Tetrahydroxy-5β-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine : Precursors of the [22,23-³H] labelled tracers. In: Chemical and Pharmaceutical Bulletin. 2010 ; Vol. 58, No. 8. pp. 1103-1106.

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abstract = "(22E)-3α,6α,7α,12α-Tetrahydroxy-5β-chol-22-en- 24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C24 3β,6β,7β,12β- tetrahydroxylated bile acid to the corresponding C22 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-Δ22-5β-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.",

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AU - Ogawa, Shoujiro

AU - Adachi, Yuuki

AU - Kakiyama, Genta

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