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

Nucleic acids research ·Vol. 5 ·No. 7 ·1978-07-00 ·Pages 2485-91

Cashmore AR, Petersen GB

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.

MeSH Terms

Animals Cattle Chemical Phenomena Chemistry DNA DNA, Bacterial Deoxycytosine Nucleotides Escherichia coli Hydrazines Mass Spectrometry Spectrophotometry, Infrared Thymus Gland

Chemicals

DNA, Bacterial Deoxycytosine Nucleotides Hydrazines DNA

Authors & Affiliations

2 authors, click to expand affiliations / ORCID

Cashmore A R

Petersen G B

References (7)

7 references, click to expand

STUDIES OF THE NUCLEOTIDE ARRANGEMENT IN DEOXYRIBONUCLEIC ACIDS. IX. SELECTIVE DEGRADATION OF PYRIMIDINE DEOXYRIBONUCLEOTIDES.
Biochim Biophys Acta. 1964 Nov 15;91:462-76 PMID: 14254018
Mapping adenines, guanines, and pyrimidines in RNA.
Nucleic Acids Res. 1977 Aug;4(8):2527-38 PMID: 409999
A new method for sequencing DNA.
Proc Natl Acad Sci U S A. 1977 Feb;74(2):560-4 PMID: 265521
The mechanism of the mutagenic action of hydroxylamines.
Prog Nucleic Acid Res Mol Biol. 1976;16:125-88 PMID: 2946
Selective reaction of methoxyamine with cytosine bases in tyrosine transfer ribonucleic acid.
J Mol Biol. 1971 Jul 28;59(2):359-73 PMID: 4935788
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 PMID: 4888872
Hydrazinolysis of some purines and pyrimidines and their related nucleosides and nucleotides.
J Chem Soc Perkin 1. 1967;16:1528-33 PMID: 5624304

Article Info

Journal

Nucleic acids research

Abbr.

Nucleic Acids Res

ISSN

0305-1048

DOI

10.1093/nar/5.7.2485

Published

1978-07-00

Pages

2485-91

Language

English

Region

England

NLM ID

0411011

PMCID

PMC342178

Subset

External Links

PubMed source DOI: 10.1093/nar/5.7.2485 PMC Full Text View journal details

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

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