Application of 2-amino-6-vinylpurine as an efficient agent for conjugation of oligonucleotides.
Attempts have been made to conjugate a variety of molecules with oligonucleotides to achieve useful functions. In this study, we have established a new efficient method for post-synthetic conjugation of oligonucleotides with the use of the 2-amino-6-vinylpurine nucleoside. Amino nucleophiles form the corresponding conjugates under acidic conditions, whereas thiol nucleophiles reacted efficiently under alkaline conditions. Thus, glutathione and HS-Cys-(Arg)8 without protecting groups were efficiently conjugated to the 2-amino-6-vinylpurine-bearing ODN under alkaline conditions. The use of 2-amino-6-vinylpurine as an agent for conjugation is advantageous in that it is stable during the reaction and may be applied to conjugation of ODNs with multiple functional molecules.
Ali
Md Monsur
MM
Graduate School of Pharmaceutical Sciences, Kyushu University, Higashi-ku, Fukuoka, Japan.
Nagatsugi
Fumi
F
Sasaki
Shigeki
S
Nakahara
Ryusuke
R
Maeda
Minoru
M
D009841:Oligonucleotides / Q000737:chemistry* / Q000378:metabolism; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000737:chemistry* / Q000378:metabolism; D014753:Vinyl Compounds / Q000737:chemistry* / Q000378:metabolism
C432203:2-amino-6-vinylpurine; D009841:Oligonucleotides; D011108:Polymers; D011687:Purines; D014753:Vinyl Compounds