Photochemical generation of C4'-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification.
[Structure: see text] We synthesized oligodeoxynucleotide (ODN, 3), which contains 4'-o-nitrobenzyloxythymidine (4) as a caged precursor of C4'-oxidized abasic site (1). Photoirradiation of 3 at 365 nm followed by amine treatment under neutral conditions afforded the lactam (2) efficiently. Duplexed ODN 3 was converted to 1 faster and more efficiently than single stranded 3, whereas amine treatment of 1 formed from single stranded 3 resulted in slightly faster lactam formation than with the duplex.
Aso
Mariko
M
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan 812-8582. aso@phar.kyushu-u.ac.jp
Usui
Kazuteru
K
Fukuda
Mitsuhiro
M
Kakihara
Yoshie
Y
Goromaru
Tsuyoshi
T
Suemune
Hiroshi
H
D000588:Amines / Q000737:chemistry*; D001483:Base Sequence; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry
D000588:Amines; D009841:Oligonucleotides