Abstract
The hydrolysis of 3-methyl-2′-deoxycytidine in aqueous solution has been investigated. Varying proportions of 3-methylcytosine, 3-methyluracil and 3-methyl-2′-deoxyuridine are formed depending upon conditions of pH and temperature. All three hydrolytic products are formed at pH 6.8 and 90°C. At pH 2, depyrimidination of 3-methylcytosine occurs as the only hydrolysis product. When the pH is increased to 12, 3-methyl-2′-deoxycytidine on heating at 90°C is completely deaminated to 3-methyl-2′-deoxyuridine with few side products formed. This reaction serves as the basis for a convenient synthesis of 3-methyl-2′-deoxyuridine. The 300 MHz spectra of 3-methyl-2′-deoxycytidine and 3-methyl-2′-deoxyuridine indicate that the sugar ring in these compounds is predominantly in 2E conformation.
Original language | English (US) |
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Pages (from-to) | 243-251 |
Number of pages | 9 |
Journal | BBA - Gene Structure and Expression |
Volume | 697 |
Issue number | 2 |
DOIs | |
State | Published - May 31 1982 |
Keywords
- Methyldeoxycytidine
- Methyldeoxycytidine synthesis
- Nucleotide hydrolysis
ASJC Scopus subject areas
- Structural Biology
- Biophysics
- Biochemistry
- Genetics