Anew pathway of histidine metabolism initiated by the adduction of glutathione to urocanic acid

M. Kinuta, H. Shimizu, N. Masuoka, Jun Ohta, W. B. Yao, K. Kjnuta, T. Ijbuka

Research output: Contribution to journalArticle

Abstract

In the first step of i.-histidine catabolism, urocanatc is formed by the action of histidinc ammonia-lyasc. In liver, urocanatc is metabolized by urocanatc hydratasc to 4-imidazolonc-5-propionatc. In epidermis, however, histidinc metabolism terminates with the formation of urocanatc, since urocanate hydratasc is absent from ihe skin. On the other hand, we found that histidinc is metabolized in part through an alternative pathway. In the first step of this pathway, 5-|2-carboxy-l-{l//-imidazol-4-yl)ethyl|glutathione [GS(CIE)|, an adduct of urocanatc and glutathionc. is formed. GS(CIE) is catabolizcd to ('ys(CIE)-Gly and then to Cys(ClE) just like the metabolism of glutathionc. Cys(CIE) is "further metabolized lo /VAc-Cys(CIE). CIE-3-mcrcaptolactate also is formed from ('ys(CIE) via an intermediate CIE-3-mercaptopyruvatc. These metabolites were isolated from normal human urine. CIE-2-mercaptnacetatc also was isolated from the urine, and its precursor is postulated to be CIE-2-mcrcaptoacctaldehyde. The /V-acetylating enzyme acting upon the formation of /VAc-Cys(CIE) recognizes the stcrcoisomcrism of asymmetric carbon atoms on Cys(CIE) molecule, while no recognition of stcreoisomcrism occurs in enzymatic degradation of GS(C'IE) to Cys(CIE) through a formation of Cys(CIE)-Gly. The formation of Cys(CIE) may participate in part in the accumulation and the elimination of the epidermal urocanatc under conditions of sunlight irradiation.

Original languageEnglish
JournalFASEB Journal
Volume11
Issue number9
Publication statusPublished - 1997

Fingerprint

Urocanic Acid
histidine
Histidine
Metabolism
Glutathione
glutathione
metabolism
acids
urine
Metabolites
Ammonia
Urine
Liver
Skin
imidazoles
Carbon
Sunlight
epidermis (animal)
Irradiation
skin (animal)

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Cell Biology

Cite this

Kinuta, M., Shimizu, H., Masuoka, N., Ohta, J., Yao, W. B., Kjnuta, K., & Ijbuka, T. (1997). Anew pathway of histidine metabolism initiated by the adduction of glutathione to urocanic acid. FASEB Journal, 11(9).

Anew pathway of histidine metabolism initiated by the adduction of glutathione to urocanic acid. / Kinuta, M.; Shimizu, H.; Masuoka, N.; Ohta, Jun; Yao, W. B.; Kjnuta, K.; Ijbuka, T.

In: FASEB Journal, Vol. 11, No. 9, 1997.

Research output: Contribution to journalArticle

Kinuta, M, Shimizu, H, Masuoka, N, Ohta, J, Yao, WB, Kjnuta, K & Ijbuka, T 1997, 'Anew pathway of histidine metabolism initiated by the adduction of glutathione to urocanic acid', FASEB Journal, vol. 11, no. 9.
Kinuta, M. ; Shimizu, H. ; Masuoka, N. ; Ohta, Jun ; Yao, W. B. ; Kjnuta, K. ; Ijbuka, T. / Anew pathway of histidine metabolism initiated by the adduction of glutathione to urocanic acid. In: FASEB Journal. 1997 ; Vol. 11, No. 9.
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abstract = "In the first step of i.-histidine catabolism, urocanatc is formed by the action of histidinc ammonia-lyasc. In liver, urocanatc is metabolized by urocanatc hydratasc to 4-imidazolonc-5-propionatc. In epidermis, however, histidinc metabolism terminates with the formation of urocanatc, since urocanate hydratasc is absent from ihe skin. On the other hand, we found that histidinc is metabolized in part through an alternative pathway. In the first step of this pathway, 5-|2-carboxy-l-{l//-imidazol-4-yl)ethyl|glutathione [GS(CIE)|, an adduct of urocanatc and glutathionc. is formed. GS(CIE) is catabolizcd to ('ys(CIE)-Gly and then to Cys(ClE) just like the metabolism of glutathionc. Cys(CIE) is {"}further metabolized lo /VAc-Cys(CIE). CIE-3-mcrcaptolactate also is formed from ('ys(CIE) via an intermediate CIE-3-mercaptopyruvatc. These metabolites were isolated from normal human urine. CIE-2-mercaptnacetatc also was isolated from the urine, and its precursor is postulated to be CIE-2-mcrcaptoacctaldehyde. The /V-acetylating enzyme acting upon the formation of /VAc-Cys(CIE) recognizes the stcrcoisomcrism of asymmetric carbon atoms on Cys(CIE) molecule, while no recognition of stcreoisomcrism occurs in enzymatic degradation of GS(C'IE) to Cys(CIE) through a formation of Cys(CIE)-Gly. The formation of Cys(CIE) may participate in part in the accumulation and the elimination of the epidermal urocanatc under conditions of sunlight irradiation.",
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AU - Kinuta, M.

AU - Shimizu, H.

AU - Masuoka, N.

AU - Ohta, Jun

AU - Yao, W. B.

AU - Kjnuta, K.

AU - Ijbuka, T.

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