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Synthesis and Hybridization Properties of Oligonucleotides Containing (2 S ,3 R )-9-(2,3,4-Trihydroxybutyl)Adenine
Authors:Yoshihito Ueno  Shinji Ishihara  Yasutomo Ito  Yukio Kitade
Affiliation:1. Department of Biomolecular Science, Faculty of Engineering, and Center for Emerging Infectious Diseases , Gifu University , Yanagido , Gifu , Japan;2. Department of Biomolecular Science, Faculty of Engineering , Gifu University , Yanagido , Gifu , Japan;3. Department of Biomolecular Science, Faculty of Engineering, and Center for Emerging Infectious Diseases, and Center for Advanced Drug Research , Gifu University , Yanagido , Gifu , Japan
Abstract:

The synthesis and properties of oligonucleotides (ONs) containing 9-(2,3,4-trihydroxybutyl)adenine, A C2 and A C3, are described. The ON containing A C2 involves the 3′ → 4′ and 3′ → 5′ phosphodiester linkages in the strand, whereas that containing A C3 possesses the 3′ → 4′ and 2′ → 5′ phosphodiester linkages. It was found that incorporation of the analogs, A C2 or A C3, into ONs significantly reduces the thermal and thermodynamic stabilities of the ON/DNA duplexes, but does not largely decrease the thermal and thermodynamic stabilities of the ON/RNA duplexes as compared with the case of the ON/DNA duplexes. It was revealed that the base recognition ability of A C2 is greater than that of A C3 in the ON/RNA duplexes.
Keywords:Acyclonucleoside  Oligonucleotides  Thermal stability  Thermodynamic stability
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