Advertisement

Crosslinking of Nucleic Acids and Proteins by Bisulfite

  • Robert Shapiro
  • Aviv Gazit
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 86A)

Abstract

Sodium bisulfite is a food and beverage additive. It is also a salt of the urban air pollutant, sulfur dioxide. Bisulfite catalyzes, at neutral pH and physiological temperatures, the transamination reactions of cytosine.derivatives with amines. The products of the reactions are N4-substituted cytosines. Both the α-and ε-amino groups of L-lysine react with cytosine, and its nucleosides, in the presence of bisulfite. Bisulfite catalyzes the binding of cytosine to polylysine, lysine to polycytidylic acid, and polylysine to polycytidylic acid. Polylysine crosslinks with heat-denatured, but not native, calf thymus DNA, in the presence of bisulfite. Other workers have demonstrated cross-linking of viral RNA with maturation and coat protein, after treatment of bacteriophage MS2 with bisulfite. Nucleic acid-protein crosslinking reactions may contribute to the adverse effects of sulfur dioxide and bisulfite upon health.

Keywords

Coat Protein Sulfur Dioxide Crosslinking Reaction Sodium Bisulfite Transamination Reaction 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Boni, I.V. and Budowsky, E.I. (1973). Transformation of non-covalent interactions in nucleoproteins into covalent bonds induced by nucleophilic reagents. I. The preparation and properties of the products of bisulfite ion-catalyzed reaction amino acids and peptides with cytosine derivatives. J. Biochem. (Tokyo), 73, 821–830.PubMedGoogle Scholar
  2. Budowsky, E.I., Simukova, N.A., Turchinsky, M.F., Boni, I.V. and Skoblov, Yu. M. (1976). Induced formation of covalent bonds between nucleoprotein components. V. UV or bisulfite induced polynucleotide-protein crosslinkage in bacteriophage MS2. Nucleic Acids Res., 3, 261–276.PubMedGoogle Scholar
  3. Chichester, D.F. and Tanner, F.W. Jr. (1972). Antimicrobial food additives, T.E. Furia ed. Handbook of Food Additives, 2nd Ed., CRC Press, Cleveland, pp 115–184.Google Scholar
  4. Institute of Food Technologists (1976). Sulfites as food additives. Nutrition Revs., 34, 58–62.Google Scholar
  5. Janion, C. and Shugar, D. (1967). Reactions of amines with dihydro-cytosine analogs and formation of amino acid and peptidyl derivatives of dihydropyrimidines. Acta Biochim. Polon., 14, 293–302.Google Scholar
  6. Levina, CS. and Mirzabekov, A.D. (1975). Covalent bonding of proteins to DNA in chromatin. Doklady Biochem., 221, 172–175.Google Scholar
  7. Shapiro, R. and Klein, R.S. (1967). Reactions of cytosine derivatives with acidic buffer solutions. II. Studies on transamination, deamination, and deuterium exchange. Biochemistry, 7 3576–3582.CrossRefGoogle Scholar
  8. Shapiro, R., Law, D.C.F. and Weisgras, J.M. (1972). A new chemical probe for single-stranded RNA. Biochem. Biophys. Res. Commun., 49, 358–363.CrossRefGoogle Scholar
  9. Shapiro, R. and Weisgras, J.M. (1970). Bisulfite-catalyzed transamination of cytosine and cytidine. Biochem. Biophys. Res.Commun., 40, 839–843.PubMedCrossRefGoogle Scholar
  10. Tikchonenko, T.I., Kisseleva, N.P., Zintshenko, A.I., Ulanov, B.P. and Budowsky, E.I. (1973). Peculiarities of the secondary structure of bacteriophage DNA in situ. IV. Covalent crosslinks between DNA and protein that arise in the reaction of Sd phage with O-methylhydroxylamine, J. Mol. Biol., 73, 109–119.PubMedCrossRefGoogle Scholar
  11. U.S. Department of Health, Education and Welfare (1969). Air Air Quality Criteria for Sulfur Oxides. National Air Pollution Control Administration Publication No. AP-50, Washington, D.C.Google Scholar

Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • Robert Shapiro
    • 1
  • Aviv Gazit
    • 1
  1. 1.Department of ChemistryNew York UniversityNew YorkUSA

Personalised recommendations