An improved synthesis of taurine- and glycine-conjugated bile acids

A simple and efficient method for the synthesis of taurine- and glycine-conjugated bile acids is described. The condensation reaction was achieved by the simple mixing of unconjugated bile acid (1.0 eq.), taurine (2.0 eq.) (or glycinate ester), diethyl phosphorocyanidate (1.2 eq.) in the presence of triethylamine at room temperature for 30-60 min. Sample clean-up was effected by the use of a prepacked Sep-Pak C18 cartridge for reversed-phase solid extraction or by direct recrystallization, yielding the desired taurine and glycine conjugates in 89-93 and 92-96% isolated yields, respectively.