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The Use of 19F NMR in the Study of Protein Alkylation by Fluorinated Reactive Intermediates

  • James W. Harris
  • M. W. Anders
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 283)

Abstract

Cysteine S-conjugates are formed as a result of enzymatic conjugation of xenobiotics with the tripeptide glutathione and subsequent peptidase cleavage. Enzymatic N-acetylation of cysteine S-conjugates yields the corresponding mercapturic acids, which are excreted in the urine. Thus glutathione and cysteine S-conjugate formation are associated with detoxication and excretion of xenobiotics. However, cysteine S-conjugate β-lyase, which is identical to glutamine transaminase K, catalyzes β-elimination reactions of cysteine S-conjugates, yielding a thiolate, pyruvate, and ammonia.

Keywords

Nuclear Magnetic Resonance Nuclear Magnetic Resonance Spectrum Nuclear Magnetic Resonance Signal Mercapturic Acid Nuclear Magnetic Resonance Tube 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Anders, M. W. (1988). Glutathione-dependent toxicity: Biosynthesis and bioactivation of cytotoxic S-conjugates. ISI Atlas of Science: Pharmacology 2, 99-104.Google Scholar
  2. Commandeur, J. N. M., De Kanter, F. J. J., and Vermeulen, N. P. E. (1989). Bioactivation of the cysteine S-conjugate and mercapturic acid of tetrafluoroethylene to acylating reactive intermediates in the rat: Dependence of activation and deactivation activities on acetyl coenzyme A availability. Mol. Pharm. 36, 654 - 663.Google Scholar
  3. Dekant, W., Lash, L. H., and Anders, M. W. (1987). Bioactivation mechanism of the cytotoxic and nephrotoxic S-conjugate S-(2-chloro-1,1,2-trifluoroethyl)-Lcysteine. Proc. Natl. Acad. Sci. USA 84, 7443 - 7447.CrossRefPubMedGoogle Scholar
  4. Sun, J. D., and Dent, J. G. (1980). A new method for measuring covalent binding of chemicals to cellular macromolecules. Chem.-Biol. Interact. 32, 41 - 61.CrossRefPubMedGoogle Scholar

Copyright information

© Plenum Press, New York 1991

Authors and Affiliations

  • James W. Harris
    • 1
  • M. W. Anders
    • 1
  1. 1.Department of Pharmacology and Environmental Health Sciences CenterUniversity of RochesterRochesterUSA

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