重氮烷与1-取代的2,4-二氧代嘧啶的反应。O2、N-3和O4-烷基产物的形成。
Reaction of diazoalkanes with 1-substituted 2, 4-dioxopyrimidines. Formation of O2, N-3 and O4-alkyl products.
作者信息
Kuśmierek J T, Singer B
出版信息
Nucleic Acids Res. 1976 Apr;3(4):989-1000. doi: 10.1093/nar/3.4.989.
Abstract
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.
摘要
在非水溶液中，重氮甲烷和重氮乙烷与尿苷、胸苷、1-甲基尿嘧啶和1-甲基胸腺嘧啶的O2、O4和N-3位点发生反应。重氮乙烷对氧进行烷基化的亲和力比重氮甲烷更高。O2:O4:N-3甲基产物的相对比例为1:2:16，而乙基产物的比例为1:1:2。当在中性缓冲溶液中进行重氮乙烷反应时，发现O2:O4:N-3乙基产物的比例相同，但反应程度非常低。O2-烷基化极大地使胸苷和尿苷的糖苷键对酸水解不稳定。所有O2和O4烷基1-取代的2,4-二氧代嘧啶在弱酸中都会脱烷基，但O2烷基更稳定。
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