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Identification of S-carboxymethyl-thiopyruvate as the product of oxidative deamination of S-carboxymethyl-cysteine

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Summary

Bromopyruvic acid and thioglycolic acid react to form carboxymethylthiopyruvic acid, which was then isolated as the 2,4-dinitrophenylhydrazone. Chromatographic and spectral properties of the compound have been investigated. Using this as a reference standard, it has been possible to demonstrate that carboxymethylthiopyruvate is the main product of the oxidative deamination of carboxymethylcysteine, D-isomer, catalyzed by D-aspartate oxidase. It has been demonstrated moreover that carboxymethylcysteine, L-isomer, may be a substrate for snake venom L-aminoacid oxidase.

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Abbreviations

CMC:

S-carboxymethyl-cysteine

CMTP:

S-carboxymethyl-thiopyruvic acid

2,4-DNPH:

2,4-dinitrophelylhydrazine

DNPH:

2,4-dinitrophenylhydrazone

d-aspartate oxidase:

d-aspartate: O2 oxidoreductase, deaminating, E.C. 1.4.3.1

l-aminoacid oxidase:

l-aminoacid: O2 oxidoreductase, deaminating, E.C. 1.4.3.2

d-aminoacid oxidase:

d-aminoacid: O2 oxidoreductase, deaminating, E.C. 1.4.3.3

l-glutamic dehydrogenase:

l-glutamate: NAD oxidoreductase, deaminating, E.C. 1.4.1.2.

References

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Authors and Affiliations

  1. Department of Biochemistry, University of Cagliari, 09100, Cagliari, Italy

    C. De Marco, A. Rinaldi, G. Piccaluga & M. B. Fadda

Authors
  1. C. De Marco
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  2. A. Rinaldi
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  3. G. Piccaluga
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  4. M. B. Fadda
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De Marco, C., Rinaldi, A., Piccaluga, G. et al. Identification of S-carboxymethyl-thiopyruvate as the product of oxidative deamination of S-carboxymethyl-cysteine. Mol Cell Biochem 3, 3–7 (1974). https://doi.org/10.1007/BF01660071

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  • DOI: https://doi.org/10.1007/BF01660071

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