Synthesis of oligonucleotides containing 2-N-heteroarylguanine residues and their effect on duplex/triplex stability,Organic & Biomolecular Chemistry

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Synthesis of oligonucleotides containing 2-N-heteroarylguanine residues and their effect on duplex/triplex stability
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1039/c7ob01875d
Takeshi Inde _{1,

2,

3,

4} , Yoshiaki Masaki _{1,

2,

3,

4} , Atsuya Maruyama _{1,

2,

3,

4} , Yu Ito _{1,

2,

3,

4} , Naoaki Makio _{1,

2,

3,

4} , Yuya Miyatake _{1,

2,

3,

4} , Takahito Tomori _{1,

2,

3,

4} , Mitsuo Sekine _{1,

2,

3,

4} , Kohji Seio _{1,

2,

3,

4}

Affiliation

To systematically understand the effect of 2-N-heteroarylguanine (G^HA) modification on the stability of higher-order DNA structures, nucleoside derivatives and oligodeoxyribonucleotides containing guanine residues modified with four kinds of hereroaryl groups on the 2-amino group were synthesized. The stabilities of the DNA duplex and the parallel-oriented DNA triplex containing these G^HAs were studied by measuring their melting temperatures (T_m). T_m experiments and DFT calculations of the modified guanine nucleobases suggested that the base pair formation energy and stability of the two conformations, i.e., the open- and closed-type conformations, are key to determining the stability of the DNA duplex. Finally, the DNA triplex was destabilized when modified guanine residues were introduced into triplex-forming oligonucleotides.

中文翻译：

含2-N-杂芳基鸟嘌呤残基的寡核苷酸的合成及其对双链/三链稳定性的影响

为了系统地理解2-N-杂芳基鸟嘌呤（G ^HA）修饰对高级DNA结构稳定性的影响，合成了在2-氨基基团上含有被四种异戊基芳基修饰的鸟嘌呤残基的核苷衍生物和寡脱氧核糖核苷酸。通过测量它们的解链温度（T _m），研究了包含这些G ^HA的DNA双链体和平行定向DNA三链体的稳定性。T _m实验和修饰鸟嘌呤核苷碱基的DFT计算表明，碱基对的形成能和两个构象的稳定性，即，开放和封闭的构型，是决定DNA双链体稳定性的关键。最后，当将修饰的鸟嘌呤残基引入形成三链体的寡核苷酸中时，DNA三链体不稳定。

更新日期：2017-09-22

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