NDI and DAN DNA: nucleic acid-directed assembly of NDI and DAN.
NDI and DAN DNA: nucleic acid-directed assembly of NDI and DAN.
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DOI：
10.1021/jo402704z
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发表时间：
2014-03-07
期刊：
影响因子：
--
通讯作者：
Iverson BL
中科院分区：
文献类型：
--
作者：
Ikkanda BA;Samuel SA;Iverson BL
设计、合成了两种新的DNA碱基替代亚磷酰胺1和2，分别基于相对富电子的1，5-二烷氧基萘（DAN）和相对缺电子的1，4，5，8-萘四羧酸二酰亚胺（NDI）。将DAN和NDI人工DNA碱基以各种顺序排列插入12聚体寡核苷酸双链体内部的三个碱基对区域内，并用CD光谱和UV熔解曲线分析进行研究。CD光谱表明修饰的双链体为B型DNA拓扑结构。解链曲线分析揭示了DNA双链体稳定性的趋势，其与水溶液中DAN和NDI部分的已知缔合以及NDI和天然DNA碱基对之间的已知有利相互作用相关。这表明DNA双链体稳定性和特异性可以由DAN和NDI之间的静电互补性驱动。在最有利的情况下，发现DNA双链体中间的NDI-DAN-NDI排列近似与三个A-T碱基对一样稳定。
Two novel DNA base surrogate phosphoramidites 1 and 2, based upon relatively electron-rich 1,5-dialkoxynaphthalene (DAN) and relatively electron-deficient 1,4,5,8-naphthalenetetracarboxylic diimide (NDI), respectively, were designed, synthesized, and incorporated into DNA oligonucleotide strands. The DAN and NDI artificial DNA bases were inserted within a three-base-pair region within the interior of a 12-mer oligonucleotide duplex in various sequential arrangements and investigated with CD spectroscopy and UV melting curve analysis. The CD spectra of the modified duplexes indicated B-form DNA topology. Melting curve analyses revealed trends in DNA duplex stability that correlate with the known association of DAN and NDI moieties in aqueous solution as well as the known favorable interactions between NDI and natural DNA base pairs. This demonstrates that DNA duplex stability and specificity can be driven by the electrostatic complementarity between DAN and NDI. In the most favorable case, an NDI–DAN–NDI arrangement in the middle of the DNA duplex was found to be approximately as stabilizing as three A–T base pairs.
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