Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA

Yu Ito; Yoshiaki Masaki; Takashi Kanamori; Akihiro Ohkubo; Kohji Seio; Mitsuo Sekine

doi:10.1016/j.bmcl.2015.11.003

Synthesis of 5-[3-(2-aminopyrimidin-4-yl)aminopropyn-1-yl]uracil derivative that recognizes Ade-Thy base pairs in double-stranded DNA

Bioorg Med Chem Lett. 2016 Jan 1;26(1):194-6. doi: 10.1016/j.bmcl.2015.11.003. Epub 2015 Nov 2.

Authors

Yu Ito¹, Yoshiaki Masaki¹, Takashi Kanamori¹, Akihiro Ohkubo¹, Kohji Seio², Mitsuo Sekine³

Affiliations

¹ Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan.
² Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan. Electronic address: kseio@bio.titech.ac.jp.
³ Department of Life Science, Tokyo Institute of Technology, 4259, Nagatsuta, Yokohama 226-8501, Japan. Electronic address: msekine@bio.titech.ac.jp.

PMID: 26602276
DOI: 10.1016/j.bmcl.2015.11.003

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.

Keywords: Antigene method; Base pair recognition; C-5 modified nucleoside; Hybridization ability; Triplex forming oligonucleotide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / chemistry*
Base Pairing*
DNA / chemistry*
Thymine / chemistry*
Uracil / analogs & derivatives*
Uracil / chemical synthesis*
Uracil / chemistry

Substances

Uracil
DNA
Adenosine
Thymine