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Amino Acids

, Volume 13, Issue 2, pp 163–169 | Cite as

Identification ofS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid with a metabolic intermediate betweenS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-l-cysteine andS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid

  • M. Kinuta
  • H. Shimizu
  • N. Masuoka
  • J. Ohta
  • W. -B. Yao
  • T. Ubuka
Full Papers

Summary

S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid (I) was chemically synthesized in 15% yield by incubating a reaction mixture oftrans-urocanic acid and 3-fold excess of 3-mercaptopyruvic acid at 45°C for 6 days. The synthesized compound was characterized by fast-atom-bombardment mass spectrometry and high-voltage paper electrophoresis. CompoundI was identified with a product of an enzymatic reaction ofS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-l-cysteine (II) with rat liver homogenate in a phosphate buffer, pH 7.4. CompoundI was degraded toS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid (III), a compound previously found in human urine [Kinuta et al. (1994) Biochem J 297: 475–478], by incubation with rat liver homogenate. From these results, we suggest that compoundI is a metabolic intermediate for the formation of compoundIII from compoundII. The present pathway follows a formation of compoundII fromS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl] gluthathione [Kinuta et al. (1993) Biochim Biophys Acta 1157: 192–198], a proposed metabolite ofl-histidine.

Keywords

Amino acids Imidazole compound Mercaptopyruvic acid Urocanic acid Histidine Mass spectrometry Paper electrophoresis 

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Copyright information

© Springer-Verlag 1997

Authors and Affiliations

  • M. Kinuta
    • 1
  • H. Shimizu
    • 1
  • N. Masuoka
    • 1
  • J. Ohta
    • 1
  • W. -B. Yao
    • 1
  • T. Ubuka
    • 1
  1. 1.Department of BiochemistryOkayama University Medical SchoolOkayamaJapan

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