Preparation of an Artificial Ribonucleoside with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone as a Base and its Discriminating Ability for Natural Nucleosides

Taisuke      Hirano; Kenji      Kuroda; Hidehiko      Kodama; Masanori      Kataoka; Yoshihiro      Hayakawa

Abstract

An artificial ribonucleoside with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone (PPT) as a nucleobase was prepared, and its binding affinity for natural nucleosides, e.g., 2-deoxyadenosine, 2-deoxycytidine, 2- deoxyguanosine, and thymidine derivatives, was investigated. This investigation revealed that, as expected, the nucleoside with PPT has good binding affinity for the four natural nucleosides to form with them some stable complexes in dimethyl sulfoxide, though the structure of the complex is not clear yet. Thus, this artificial nucleoside has high potential as a universal nucleoside.

Keywords: Nucleosides, nitrogen heterocycles, tautomerism

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Letters in Organic Chemistry

Title: Preparation of an Artificial Ribonucleoside with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone as a Base and its Discriminating Ability for Natural Nucleosides

Volume: 4 Issue: 8

Author(s): Taisuke Hirano, Kenji Kuroda, Hidehiko Kodama, Masanori Kataoka and Yoshihiro Hayakawa

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Keywords: Nucleosides, nitrogen heterocycles, tautomerism

Abstract: An artificial ribonucleoside with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone (PPT) as a nucleobase was prepared, and its binding affinity for natural nucleosides, e.g., 2-deoxyadenosine, 2-deoxycytidine, 2- deoxyguanosine, and thymidine derivatives, was investigated. This investigation revealed that, as expected, the nucleoside with PPT has good binding affinity for the four natural nucleosides to form with them some stable complexes in dimethyl sulfoxide, though the structure of the complex is not clear yet. Thus, this artificial nucleoside has high potential as a universal nucleoside.

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Hirano Taisuke, Kuroda Kenji, Kodama Hidehiko, Kataoka Masanori and Hayakawa Yoshihiro, Preparation of an Artificial Ribonucleoside with pyrimido[4,5-d]pyrimidine-2,4,5,7-(1H,3H,6H,8H)-tetraone as a Base and its Discriminating Ability for Natural Nucleosides, Letters in Organic Chemistry 2007; 4 (8) . https://dx.doi.org/10.2174/157017807782795493