Reaction of diazoalkanes with 1-substituted 2, 4-dioxopyrimidines. Formation of O2, N-3 and O4-alkyl products
| Autor: | J.T. Kuśmierek, B. Singer |
|---|---|
| Rok vydání: | 1976 |
| Předmět: |
chemistry.chemical_classification
Binding Sites Diazonium Compounds Chemical Phenomena Chromatography Paper Diazomethane Glycosidic bond Alkylation Biology Medicinal chemistry Uridine Chemistry chemistry.chemical_compound Hydrolysis Pyrimidines chemistry Biochemistry Alkanes Genetics Spectrophotometry Ultraviolet Acid hydrolysis Chromatography Thin Layer Alkyl |
| Zdroj: | Nucleic Acids Research. 3:989-1000 |
| ISSN: | 1362-4962 0305-1048 |
| DOI: | 10.1093/nar/3.4.989 |
| Popis: | In non-aqueous solution, diazomethane and diazoethane react with the O2, O4 and N-3 sites of uridine, thymidine, 1-methyluracil and 1-methylthymine. Diazoethane has a higher affinity for alkylating oxygens than does diazomethane. The relative ratio of O2:O4:N-3 methyl products is 1:2:16 and of ethyl products the ratio is 1:1:2. When the diazoethane reaction is performed in neutral buffered solution, the same proportion of O2:O4:N-3 ethyl products is found, but the extent of reaction is very low. O2-alkylation greatly labilizes the glycosidic bond of thymidine and uridine toward acid hydrolysis. All O2 and O4 alkyl 1-substituted 2,4-dioxopyrimidines are dealkylated in weak acid but the O2 alkyl group is the more stable. |
| Databáze: | OpenAIRE |
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