Photochemical Generation of C4‘-Oxidized Abasic Site Containing Oligodeoxynucleotide and Its Efficient Amine Modification

Photochemical Generation of C4‘-Oxidized Abasic Site Containing Oligodeoxynucleotide and Its Efficient Amine Modification

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 t...

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Veröffentlicht in:Organic letters 2006-07, Vol.8 (15), p.3183-3186
Hauptverfasser: Aso, Mariko, Usui, Kazuteru, Fukuda, Mitsuhiro, Kakihara, Yoshie, Goromaru, Tsuyoshi, Suemune, Hiroshi
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Base Sequence
Molecular Structure
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oxidation-Reduction
Photochemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060987v