1964 年 84 巻 11 号 p. 1104-1107
New glucuronic acid conjugate was isolated from human urine after sulfisomezole administration, according to the following extraction method. To the urine, was added active charcoal, followed by elution with ammoniacal alkaline solvents, which was absorbed through H-type (A) Dowex 50W-X8, 100-200 mesh, and later extracted with water. Lead acetate precipitates were separated. To the precipitates by basic lead acetate, ammonium sulfate solution and hydrogen sulfide were added to remove lead and then extracted with ammonia after being absorbed through A. The ammonia eluate was evaporated to dryness under reduced pressure and colorless fine crystals, m.p. 170-171° was afforded.
According to the synthetic process, potassium salt of N4-carbobenzoxysulfisomezole was condensed with methyl (2, 3, 4-tri-O-acetyl-α-D-glucosylbromid) uronate, and reduced with Pd charcoal. It was hydrolyzed with barium hydroxide, purified by paper partition chromatography and extracted with ammonia after being absorbed through A, and crystals, m.p. 170-171° was obtained. No depression of m.p. by admixture and elementary analysis, ultraviolet and infrared of both compounds extracted and synthesized are in good agreement. Therefore, this compound was identified to be ammonium sulfisomezole-N1-glucosiduronate containing one molecule of water of crystallization.