title: Photochemical generation of C4'-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification.
abstract: [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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan 812-8582. aso@phar.kyushu-u.ac.jp
authors.forename: Mariko
authors.initials: M
authors.lastname: Aso
authors.forename: Kazuteru
authors.initials: K
authors.lastname: Usui
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Fukuda
authors.forename: Yoshie
authors.initials: Y
authors.lastname: Kakihara
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Goromaru
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Suemune
mesh_terms: D000588:Amines / Q000737:chemistry*; D001483:Base Sequence; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry
chemical_list: D000588:Amines; D009841:Oligonucleotides