The synthesis of glycine conjugated 3-oxo-bile acids.
The glycine conjugates of the 3-oxo-derivatives of lithocholic, deoxycholic, chenodeoxycholic and cholic acids have been synthesized from their respective parent bile acid using established procedures. The reaction sequence involved oxidation using either chromic acid or silver carbonate--Celite followed by a conjugation step employing the peptide coupling reagent N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The final products were obtained in both high yield and purity for use as reference compounds in the analysis of conjugated bile acids in bile and faecal samples by high performance liquid chromatography. Analysis of the prepared 3-oxo-glycobile acids by fast atom bombardment negative ion mass spectrometry, infrared spectroscopy and nuclear magnetic resonance proton spectroscopy is also discussed along with the thin-layer chromatographic properties.
Henly
P J
PJ
PHLS Centre for Applied Microbiology and Research, Bacterial Metabolism Research Laboratory, Salisbury, Wiltshire, England.
Owen
R W
RW
D055598:Chemical Phenomena; D002621:Chemistry; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002793:Cholic Acids; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003840:Deoxycholic Acid / Q000031:analogs & derivatives*; D005998:Glycine; D006000:Glycocholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006002:Glycodeoxycholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008095:Lithocholic Acid; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared
D002793:Cholic Acids; D003840:Deoxycholic Acid; D002635:Chenodeoxycholic Acid; D006002:Glycodeoxycholic Acid; D008095:Lithocholic Acid; D006000:Glycocholic Acid; D005998:Glycine