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The synthesis of taurine‐conjugated bile acids and bile acid sulfates labeled with 14 C or 3 H in the taurine moiety
Author(s) -
Zhang Jie,
Griffiths William J.,
Sjövall Jan
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199702)39:2<159::aid-jlcr954>3.0.co;2-w
Subject(s) - taurine , chemistry , conjugated system , bile acid , moiety , reagent , salt (chemistry) , chromatography , organic chemistry , biochemistry , amino acid , polymer
Studies of bile acid transport systems require radio‐labeled taurine‐conjugated bile acids with high specific activity. An established synthetic procedure was optimized to provide mild, fast, and effective conjugation of radio‐labeled taurine with different types of bile acids, including those with labile 7α‐hydroxy‐3‐oxo‐Δ 4 or 3β,7α‐dihydroxy‐Δ 5 structures. Taurine labeled with 14 C or 3 H was reacted with excess bile acid anhydride formed from the tributylamine salt and ethylchloroformate (2/1 M/M) in aqueous dioxane for 15 min at room temperature. The yields were higher than 95% and less than 2% side products were formed. Bile acid sulfates were conjugated with 14 C‐ or 3 H‐ labeled taurine by using N‐ethoxycarbonyl‐2‐ethoxy‐1,2‐dihydroquinoline as the coupling reagent. The products were effectively purified by chromatography of the sodium salts on Sephadex LH‐20. The yields of taurine‐conjugated bile acid sulfates were 65–70%. © 1997 John Wiley & Sons, Ltd.