Synthesis of N-acetyl-S-(3-coumarinyl)-cysteine methyl ester and HPLC analysis of urinary coumarin metabolites.
N-Acetyl-S-(3-coumarinyl)cysteine, a metabolite of coumarin in rodents, has been synthesized as methyl ester. A new synthetic route to prepare N-acetyl-S-(3-coumarinyl)-D,L-cysteine methyl ester comprises reaction of 3-mercaptocoumarin with N-acetyl-3-chloro-D,L-alanine methyl ester. N-acetyl-S-(4-coumarinyl)-L-cysteine was obtained by reaction of 3-bromocoumarin and N-acetyl-L-cysteine. A method for the determination of N-acetyl-S-(3-coumarinyl)cysteine as its methyl ester in urine by HPLC has been developed.
Eisenbrand
Gerhard
G
Department of Chemistry, University of Kaiserslautern, D-67663 Kaiserslautern, Germany. eisenbra@rhrk.uni-kl.de
Otteneder
Michael
M
Tang
Weici
W
D002851:Chromatography, High Pressure Liquid; D003374:Coumarins / Q000138:chemical synthesis* / Q000652:urine; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000652:urine; D003553:Cystine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D017550:Spectroscopy, Fourier Transform Infrared
D003374:Coumarins; C478238:N-acetyl-S-(3-coumarinyl)-cysteine methyl ester; D003553:Cystine; D003545:Cysteine