Synthesis of the new nucleoside analogue connecting 2-amino-6-vinylpurine to the 2'-deoxyribose skeleton via the methylene linker.
We have previously reported that the 2-amino-6-vinylpurine nucleoside exhibits the highly efficient and selective cross-linking reaction toward the cytosine base at the target site in the duplex DNA. The nucleoside analogues that connect the 2-amino-6-vinylpurine to the 2'-deoxyribose skeleton through the ethylene or the butylene linker formed the cross-link selectively to the adenine base of the TA pair or the cytosine base of the GC pair in the triplex DNA, respectively. They did not form cross-link in the duplex DNA. These results lead us to study in detail the relationship between the linker length and the cross-linking ability. In this study, we describe the synthesis of the new nucleoside analogue that connects 2-amino-6-vinylpurine to the 2'-deoxyribose unit via the methylene linker.
Kurose
Yusuke
Y
Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi Higashi-ku, Fukuoka, Japan.
Taniguchi
Yosuke
Y
Nagatsugi
Fumi
F
Sasaki
Shigeki
S
D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D003855:Deoxyribose / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
C432203:2-amino-6-vinylpurine; D003432:Cross-Linking Reagents; D009841:Oligonucleotides; D011684:Purine Nucleosides; D011687:Purines; D014753:Vinyl Compounds; D015075:2-Aminopurine; D003855:Deoxyribose