title: Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA.
abstract: 5-[3-(2-Aminopyrimidin-4-yl)aminopropyn-1-yl]uracil (Ura(Pyr)) was designed as a new nucleobase to recognize Ade-Thy base pair in double-stranded DNA. We successfully synthesized the dexoynucleoside phosphoramidite having Ura(Pyr) and incorporated it into triplex forming oligonucleotides (TFOs). Melting temperature analysis revealed that introduction of Ura(Pyr) into TFOs could effectively stabilize their triplex structures without loss of base recognition capabilities.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan.
authors.forename: Yu
authors.initials: Y
authors.lastname: Ito
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan.
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Masaki
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Kanamori
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan. Electronic address: kseio@bio.titech.ac.jp.
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan. Electronic address: msekine@bio.titech.ac.jp.
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D000241:Adenosine / Q000737:chemistry*; D020029:Base Pairing; D004247:DNA / Q000737:chemistry*; D013941:Thymine / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D014498:Uracil; D004247:DNA; D000241:Adenosine; D013941:Thymine
keywords: Antigene method; Base pair recognition; C-5 modified nucleoside; Hybridization ability; Triplex forming oligonucleotide