Affiliation:
1. Department of Biochemistry, Okayama University Medical School, Okayama 700, Japan
Abstract
S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine (I), a proposed precursor of 3-[(carboxymethyl)thio]-3-(1H-imidazol-4-yl)propanoic acid [Kinuta, Yao, Masuoka, Ohta, Teraoka & Ubuka (1991) Biochem. J. 275, 617-721], was isolated from healthy human urine by using ion-exchange column chromatography. Identification of the isolated compound with compound (I) was performed by physicochemical analyses involving i.r., m.s. and n.m.r. spectrometries as well as high-voltage paper electrophoresis, t.l.c. and paper chromatography. Compound (I) was synthesized in 80% yield by incubation of a reaction mixture containing trans-urocanic acid and 3-fold excess of cysteine at 70-75 degrees C. From these results we suggest that natural thiol compounds such as cysteine and GSH participate in the metabolism of urocanic acid, a key metabolite of L-histidine.
Subject
Cell Biology,Molecular Biology,Biochemistry
Cited by
10 articles.
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1. Rhenium(I) and technetium(I) fac-M(NSO)(CO)3 (M=Re, 99mTc) tricarbonyl complexes, with a tridentate NSO bifunctional agent: Synthesis, structural characterization, and radiochemistry;Polyhedron;2010-02
2. Formation ofS-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite ofL-histidine, fromcis-urocanic acid and glutathione by the action of glutathioneS-transferase;ELECTROPHORESIS;2003-09
3. Determination ofS-[2-carboxy-1-(1H-imidazol- 4-yl)ethyl]glutathione, a novel metabolite ofL-histidine, in tissue extracts from sunlight- irradiated rat by capillary electrophoresis;ELECTROPHORESIS;2001-09
4. Inhibitory effects in vitro of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-glutathione, a proposed metabolite of l-histidine, on γ-glutamyltransferase activity;Biochimica et Biophysica Acta (BBA) - General Subjects;1998-09
5. Determination of chiral catabolites from S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione, a proposed metabolite of l-histidine, by capillary electrophoresis;Journal of Chromatography A;1998-04