Imidazolo-dC Metal-Mediated Base Pairs: Purine Nucleosides Capture Two Ag+ Ions and Form a Duplex with the Stability of a Covalent DNA Cross-Link
Imidazolo-dC Metal-Mediated Base Pairs: Purine Nucleosides Capture Two Ag+ Ions and Form a Duplex with the Stability of a Covalent DNA Cross-Link
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DOI：
10.1002/chem.201404422
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发表时间：
2014-12-01
影响因子：
4.3
通讯作者：
Seela, Frank
中科院分区：
文献类型：
--
作者：
Mei, Hui;Ingale, Sachin A.;Seela, Frank
8-苯基咪唑并-dC（（ph）ImidC，2）通过捕获两个银离子形成金属介导的DNA碱基对。为此，荧光嘌呤2-脱氧核糖核苷2已被合成并转化为亚磷酰胺6。由于核碱基去质子化的容易性，含有嘌呤骨架的新的Ag+介导的碱基对比来自吡咯并[3，4-d]嘧啶系统的碱基对强得多（（ph）PyrdC，1）。银介导的（ph）ImidC-（ph）ImidC碱基对与DNA双螺旋很好地匹配，并且具有共价交联的稳定性。这种人工金属碱基对的形成可能不限于DNA，而是可以适用于其他核酸，例如RNA、PNA和GNA以及其他生物聚合物。
8-Phenylimidazolo-dC ((ph)ImidC, 2) forms metal-mediated DNA base pairs by entrapping two silver ions. To this end, the fluorescent purine 2-deoxyribonucleoside 2 has been synthesised and converted into the phosphoramidite 6. Owing to the ease of nucleobase deprotonation, the new Ag+-mediated base pair containing a purine skeleton is much stronger than that derived from the pyrrolo- [3,4-d]pyrimidine system ((ph)PyrdC, 1). The silver-mediated (ph)ImidC-(ph)ImidC base pair fits well into the DNA double helix and has the stability of a covalent cross-link. The formation of such artificial metal base pairs might not be limited to DNA but may be applicable to other nucleic acids such as RNA, PNA and GNA as well as other biopolymers.