Generation of an abasic site in an oligonucleotide by using acid-labile 1-deaza-2'-deoxyguanosine and its application to postsynthetic modification.
We developed a new convenient method for generation of an abasic site at the 3'-terminus of an oligonucleotide. This method uses a 1-deaza-2'-deoxyguanosine residue, which easily undergoes depurination under acidic conditions. The abasic site of the oligonucleotide can be further modified with external functional groups. We report herein the chemical stability of 1-deaza-2'-deoxyguanosine in the oligodeoxynucleotide and the application to the postsynthetic modification of an oligonucleotide by utilizing the chemical property of 1-deaza-2'-deoxyguanosine. [Structure: see text]
Kojima
Naoshi
N
Research Institute of Genome-based Biofactory, National Institute of Advanced Industrial Science & Technology (AIST Hokkaido), 2-17-2-1 Tsukisamu-Higashi, Toyohira-ku, Sapporo 062-8517, Japan.
Sugino
Maiko
M
Mikami
Akiko
A
Ohtsuka
Eiko
E
Komatsu
Yasuo
Y
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013096:Spermine
C480034:1-deaza-2'-deoxyguanosine; D009281:Naphthalenes; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; C031721:naphthalene; D013096:Spermine; D003849:Deoxyguanosine