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, Jun Ohta, W. B. Yao, T. Ubuka

Research output: Contribution to journalArticle

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 - 1997

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Liver
Cysteine
Rats
Urocanic Acid
Fast Atom Bombardment Mass Spectrometry
Paper Electrophoresis
Metabolites
Electrophoresis
Histidine
Mass spectrometry
Buffers
Phosphates
Urine
Atoms
Electric potential
beta-mercaptolactate
3-mercaptopyruvic acid
S-(2-carboxy-1-(1H-imidazol-4-yl) ethyl)cysteine
S-(2-carboxy-1-(1H-imidazol-4-yl)ethyl)glutathione

Keywords

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

ASJC Scopus subject areas

  • Clinical Biochemistry
  • Biochemistry
  • Endocrinology

Cite this

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title = "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",
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.",
keywords = "Amino acids, Histidine, Imidazole compound, Mass spectrometry, Mercaptopyruvic acid, Paper electrophoresis, Urocanic acid",
author = "M. Kinuta and H. Shimizu and N. Masuoka and Jun Ohta and Yao, {W. B.} and T. Ubuka",
year = "1997",
doi = "10.1007/BF01373214",
language = "English",
volume = "13",
pages = "163--169",
journal = "Amino Acids",
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T1 - 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

AU - Kinuta, M.

AU - Shimizu, H.

AU - Masuoka, N.

AU - Ohta, Jun

AU - Yao, W. B.

AU - Ubuka, T.

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

KW - Amino acids

KW - Histidine

KW - Imidazole compound

KW - Mass spectrometry

KW - Mercaptopyruvic acid

KW - Paper electrophoresis

KW - Urocanic acid

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