Amidination of Lysine Side Chains

  • Dan S. Tawfik

Abstract

Perhaps the largest variety of modifications available is that for ε-amino group of lysine (1-4). The amino side chain can be acylated (using e.g., acetic anhydride) or alkylated by trinitrobenzenesulfonic acid (TNBS); these reactions alter both the size and the charge of the amino group. Other modifications, using anhydrides of dicarboxylic acids (e.g., succinic anhydride), replace the positively charged amino group with a negatively charged carboxyl group. Amidinations (5-6) and reductive alkylations (see ref. 7) offer an opportunity to modify the structure of the ε-amino group of lysines, while maintaining the positive charge. Modifications that usually do not disrupt the overall structure of the protein are preferred, particularly in those cases when one wishes to identify the specific role of lysine in the active site of the protein being studied.

Keywords

Formaldehyde Ethyl Hydroxide Carboxyl Lysine 

References

  1. 1.
    Means, G. E. and Feeney, R. E. (1971) Chemical Modifications of Proteins. Holden-Day, San Francisco.Google Scholar
  2. 2.
    Hirs, C. H. N. and Timasheff, S. N. (eds.) (1972) Enzyme structure B. Meth. Enzymol. 25.Google Scholar
  3. 3.
    Lundblad, R. L. and Noyes, C. M. (1984) Chemical Reagents for Protein Modifications, Vols. 1 and 2. CRC Press, Boca Raton, FL.Google Scholar
  4. 4.
    Feeney, R. E. (1987) Chemical modification of proteins: comments and perspectives. Int. J. Pept. Protein Res. 27, 145–161.Google Scholar
  5. 5.
    Hunter, M. J. and Ludwig, M. L. (1962) The reaction of imidoesters with small proteins and related small molecules. J. Amer. Chem. Soc. 84, 3491–3504.CrossRefGoogle Scholar
  6. 6.
    Wallace, C. J. A. and Harris, D. E. (1984) The preparation of fully N-e-acetimidylated cytochrome c. Biochem. J. 217, 589–594.PubMedGoogle Scholar
  7. 7.
    Jentoft, N. and Dearborn, D. G. (1979) Labeling of proteins by reductive methylation using sodium cyanoborohydride. J. Biol. Chem. 254, 4359–4365.PubMedGoogle Scholar
  8. 8.
    Fields, R. (1972) The rapid determination of amino groups with TNBS. Meth. Enzymol. 25, 464–468.CrossRefGoogle Scholar

Copyright information

© Humana Press Inc., Totowa, NJ 2002

Authors and Affiliations

  • Dan S. Tawfik
    • 1
  1. 1.Department of Biological Chemistrythe Weizman Institute of ScienceRehovotIsrael

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