Hydrazinolysis of some purines and pyrimidines and their related nucleosides and nucleotides

Abstract

Uracil and thymme and their related nucleosides and nucleotides are degraded quantitatively by treatment with hydrazine hydrate at 90°. The reaction products are, respectively, pyrazol-3-one, and 5-methylpyrazol-3-one together with, in the case of the nucleosides and nucleotides, approximately quantitative yields of urea and a sugar or sugar phosphate hydrazone. Cytosine and its derivative are similarly degraded but two heterocyclic products, 3-aminopyrazole and NN′-di(3-pyrazolyl)hydrazine are obtained. Adenine and guanine, their related nucleosides, and guanine nucleotides are not degraded by hydrazine hydrate at 90° but adenine nucleotides are slowly attacked. In this reaction the only degradation product which has been identified is inorganic phosphate.