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. 1978 Jul;5(7):2485–2491. doi: 10.1093/nar/5.7.2485

The degradation of DNA by hydrazine: identification of 3-ureidopyrazole as a product of the hydrazinolysis of deoxycytidylic acid residues.

A R Cashmore, G B Petersen
PMCID: PMC342178  PMID: 353742

Abstract

The reaction of hydrazine with the cytosine residues of DNA yields 3-ureidopyrazole, in approximately 50% yield, in addition to the expected 3-aminopyrazole. This product has been identified by ultraviolet, infrared, nuclear magnetic resonance and mass spectroscopy. A product of the reaction of hydrazine hydrate with cytosine, formulated by others as NN'-di-(3-pyrazolyl) hydrazine, has been identified as 3-ureidopyrazole.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Budowsky E. I. The mechanism of the mutagenic action of hydroxylamines. Prog Nucleic Acid Res Mol Biol. 1976;16:125–188. doi: 10.1016/s0079-6603(08)60757-6. [DOI] [PubMed] [Google Scholar]
  2. Cashmore A. R., Brown D. M., Smith J. D. Selective reaction of methoxyamine with cytosine bases in tyrosine transfer ribonucleic acid. J Mol Biol. 1971 Jul 28;59(2):359–373. doi: 10.1016/0022-2836(71)90056-8. [DOI] [PubMed] [Google Scholar]
  3. Cashmore A. R., Petersen G. B. The degradation of DNA by hydrazine: a critical study of the suitability of the reaction for the quantitative determination of purine nucleotide sequences. Biochim Biophys Acta. 1969 Feb 18;174(2):591–603. doi: 10.1016/0005-2787(69)90289-5. [DOI] [PubMed] [Google Scholar]
  4. Donis-Keller H., Maxam A. M., Gilbert W. Mapping adenines, guanines, and pyrimidines in RNA. Nucleic Acids Res. 1977 Aug;4(8):2527–2538. doi: 10.1093/nar/4.8.2527. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Hayes D. H., Hayes-Baron F. Hydrazinolysis of some purines and pyrimidines and their related nucleosides and nucleotides. J Chem Soc Perkin 1. 1967;16:1528–1533. doi: 10.1039/j39670001528. [DOI] [PubMed] [Google Scholar]
  6. Maxam A. M., Gilbert W. A new method for sequencing DNA. Proc Natl Acad Sci U S A. 1977 Feb;74(2):560–564. doi: 10.1073/pnas.74.2.560. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. TEMPERLI A., TUERLER H., RUEST P., DANON A., CHARGAFF E. STUDIES OF THE NUCLEOTIDE ARRANGEMENT IN DEOXYRIBONUCLEIC ACIDS. IX. SELECTIVE DEGRADATION OF PYRIMIDINE DEOXYRIBONUCLEOTIDES. Biochim Biophys Acta. 1964 Nov 15;91:462–476. doi: 10.1016/0926-6550(64)90076-3. [DOI] [PubMed] [Google Scholar]

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