Synthesis and characterization of the anomeric pair of 17 beta-glucuronides of ethynylestradiol.
The alpha- and beta-anomers of the 17 beta-D-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl4-promoted reaction between beta-acetoxy GAM and the t-17 beta-hydroxyl group of EE2-3-acetate. The conjugates were resolved by crystallization and HPLC. Positive identification was established by u.v. spectrophotometry, i.r. and mass spectrometry and 1H- and 13C-n.m.r. The structure of the beta-anomer was confirmed by X-ray crystallographic analysis. In addition, the alpha-anomer was refractory to hydrolysis by bovine beta-glucuronidase, establishing a biochemical difference between the conjugate pair.
D002851:Chromatography, High Pressure Liquid; D004997:Ethinyl Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007536:Isomerism; D008958:Models, Molecular; D013055:Spectrophotometry, Infrared
C024860:ethinyl estradiol glucuronide; D004997:Ethinyl Estradiol