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 | |
| Publication status | Published - 2010 Aug 1 |
Keywords
- Bile acid
- Gycine conjugate
- N-acylamidation
- Taurine conjugate
- Tetrahydroxy-Δ-5β-cholenoic acid
- Wittig reaction
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery
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Cite this
Ogawa, S., Adachi, Y., Kakiyama, G., Simada, 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