Synthesis of an oligonucleotide with a nicotinamide mononucleotide residue and its molecular recognition in DNA helices.
Synthesis of an oligonucleotide with a nicotinamide mononucleotide residue and its molecular recognition in DNA helices.
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具有烟酰胺单核苷酸残基的寡核苷酸的合成及其在DNA螺旋中的分子识别
DOI：
10.1039/c5ob01714a
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发表时间：
2015
影响因子：
3.2
通讯作者：
C. Richert
中科院分区：
文献类型：
--
作者：
A. Göckel;C. Richert
烟酰胺腺嘌呤二核苷酸（NAD）是初级代谢的关键氧化还原辅因子。其氧化还原反应性基于烟酰胺单核苷酸（NMN）部分。我们研究了当掺入寡核苷酸中时，NMN+是否可以参与配对相互作用。在这里，我们描述了在溶液中通过氨基磷酸酯偶联在寡脱氧核苷酸的3′-末端掺入NMN+。在UV熔解曲线中测量具有含NMN+链的双链体和三链体的稳定性。虽然具有面向烟酰胺的不同碱基的双链体的熔点相似，但三链体稳定性在不同碱基组合之间变化很大，表明特异性配对。最稳定的三链体被发现时，鸟嘌呤和腺嘌呤面临的NMN+残基。它们的三链体熔点高于在相同位置具有胸苷残基的相应三链体的熔点。这些结果表明，NMN+残基可以在DNA螺旋中被选择性地识别，因此与核酸中的分子识别相容。
Nicotinamide adenine dinucleotide (NAD) is a pivotal redox cofactor of primary metabolism. Its redox reactivity is based on the nicotinamide mononucleotide (NMN) moiety. We investigated whether NMN+ can engage in pairing interactions, when incorporated into an oligonucleotide. Here we describe the incorporation of NMN+ at the 3′-terminus of an oligodeoxynucleotide via a phosphoramidate coupling in solution. The stability of duplexes and triplexes with the NMN+-containing strand was measured in UV-melting curves. While the melting points of duplexes with different bases facing the nicotinamide were similar, triplex stabilities varied greatly between different base combinations, suggesting specific pairing. The most stable triplexes were found when a guanine and an adenine were facing the NMN+ residue. Their triplex melting points were higher than those of the corresponding triplexes with a thymidine residue at the same position. These results show that NMN+ residues can be recognized selectively in DNA helices and are thus compatible with the molecular recognition in nucleic acids.
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