Predicted exocyclic amino group alkylation of 2'-deoxyadenosine and 2'-deoxyguanosine by the isopropyl cation.
Predicted exocyclic amino group alkylation of 2'-deoxyadenosine and 2'-deoxyguanosine by the isopropyl cation.
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预测异丙基阳离子对 2-脱氧腺苷和 2-脱氧鸟苷的环外氨基烷基化。
DOI：
10.1021/tx000059j
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发表时间：
2000
影响因子：
4.1
通讯作者：
Fishbein,JC
中科院分区：
文献类型：
--
作者：
Blans,P;Fishbein,JC
二异丙基三氮烯在 10% 乙腈水溶液（pH 7.0 ± 0.4）中生成主要产物 N6-异丙基-2'-脱氧 Ado，并生成 N2-异丙基-2'-脱氧Guo，其产率分别与 2'-脱氧Ado 和 2'-脱氧Guo 反应中的 O6 加合物相当。这些观察结果与基于关于决定重氮离子介导的烷基化中原子位点选择性的因素的现有假设的预期不一致。基于所涉及的反应中间体的短暂存在的另一种解释与这些观察结果一致。
Diisopropyltriazene in aqueous 10% acetonitrile (pH 7.0 ± 0.4) yieldsN6-isopropyl-2‘-deoxyAdo as the predominant product andN2-isopropyl-2‘-deoxyGuo in yields comparable with the O6adduct in reactions with 2‘-deoxyAdo and 2‘-deoxyGuo, respectively. These observations are inconsistent with what is expected on the basis of the regnant hypothesis concerning factors that determine atom site selectivity in diazonium ion-mediated alkylations. An alternative explanation based on the fleeting existence of the reactive intermediates involved is consistent with these observations.