86386-60-9Relevant articles and documents
Chemical synthesis, structural analysis, and decomposition of N-nitroso bile acid conjugates
Dayal, Bishambar,Bhojawala, Jalpa,Rapole, Keshava R.,Pramanik, Birendra N.,Ertel, Norman H.,Shefer, Sarah,Salen, Gerald
, p. 885 - 890 (2007/10/03)
N-nitrosoamides of 7β-hydroxylated bile acid conjugates, particularly of the ursodeoxycholic acid family have been synthesized. The products and synthetic intermediates were fully characterized by the results of high- resolution 1H NMR, FT-1R, FABMS and ESI-MS studies. The compounds, N- nitrosoglycoursodeoxycholic acid (NOGUDCA), N-nitrosoglycoursocholic acid (NOGUCA) and N-nitrosoglycodeoxycholic acid (NOGDCA) decomposed between pH 6 and 9 in aqueous bullet solutions, indicating a t( 1/2 ) of 5-7 h while N- nitrosotauroursodeoxycholic acid (NOTUDCA) indicated a much longer t( 1/2 ) of 15-17 h. These results suggest that the compounds are relatively stable and may enter the enterohepatic circulation. Their decomposition is similar to that of other N-nitrosamides, which generate alkylating agents and thereby act as DNA mutagens.
An improved procedure for the synthesis of glycine and taurine conjugates of bile acids
Tserng,Hachey,Klein
, p. 404 - 407 (2007/10/06)
Glycine and taurine conjugates of 5β cholanic acids have been synthesized using improved procedures based on the peptide coupling reagent, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The conjugates are obtained in chromatographically pure form in yields higher than 90%. The use of this procedure in the large scale preparation of choly[1,2 13C2]glycine is described.