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

University Hospital

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1103-1106
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	58
Issue number	8
DOIs	https://doi.org/10.1248/cpb.58.1103
Publication status	Published - 2010 Aug

Keywords

Bile acid
Gycine conjugate
N-acylamidation
Taurine conjugate
Tetrahydroxy-Δ-5β-cholenoic acid
Wittig reaction

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.58.1103

Cite this

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 et al.

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

Research output: Contribution to journal › Article › peer-review

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

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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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