Identification of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid with a metabolic intermediate between S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteine and S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid

M. Kinuta, H. Shimizu, N. Masuoka, J. Ohta, W. B. Yao, T. Ubuka

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid (I) was chemically synthesized in 15% yield by incubating a reaction mixture of trans-urocanic acid and 3-fold excess of 3-mercaptopyruvic acid at 45°C or 6 days. The synthesized compound was characterized by fast-atom-bombardment mass spectrometry and high-voltage paper electrophoresis. Compound I was identified with a product of an enzymatic reaction of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteine (II) with rat liver homogenate in a phosphate buffer, pH 7.4. Compound I was degraded to S-[2-carboxy-1(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid (III), a compound previously found in human urine, by incubation with rat liver homogenate. From these results, we suggest that compound I is a metabolic intermediate for the formation of compound III from compound II. The present pathway follows a formation of compound II from S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]gluthathione, a proposed metabolite of L-histidine.

Original languageEnglish
Pages (from-to)163-169
Number of pages7
JournalAmino Acids
Volume13
Issue number2
DOIs
Publication statusPublished - Oct 22 1997

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

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