Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification

Mariko Aso; Kazuteru Usui; Mitsuhiro Fukuda; Yoshie Kakihara; Tsuyoshi Goromaru; Hiroshi Suemune

doi:10.1021/ol060987v

Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification

Mariko Aso, Kazuteru Usui, Mitsuhiro Fukuda, Yoshie Kakihara, Tsuyoshi Goromaru, Hiroshi Suemune

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3183-3186
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	15
DOIs	https://doi.org/10.1021/ol060987v
Publication status	Published - Jul 20 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol060987v

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abstract = "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.",

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T1 - Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification

AU - Aso, Mariko

AU - Usui, Kazuteru

AU - Fukuda, Mitsuhiro

AU - Kakihara, Yoshie

AU - Goromaru, Tsuyoshi

AU - Suemune, Hiroshi

PY - 2006/7/20

Y1 - 2006/7/20

N2 - 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.

AB - 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.

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JO - Organic Letters

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Photochemical generation of C4′-oxidized abasic site containing oligodeoxynucleotide and its efficient amine modification

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