Synthesis of monosulfates of unconjugated and conjugated bile acids.

Abstract

The 3-, 7- and 12-monosulfates of unconjugated, and glycine- and taurine-conjugated bile acids were prepared. Bile acid derivatives protected by appropriate groups were sulfated in the usual manner with chlorosulfonic acid in pyridine. Subsequent removal of the protecting groups provided the desired sulfates of bile acids in satisfactory yields. The NMR spectral properties of sulfated bile acids and related compounds are briefly discussed. The sulfation of bile acids is important in the study of certain liver diseases.