The photoreactivity of the caged precursors of oligonucleotides containing C4'-oxidized abasic site and reaction of the generated lesion.

Kazuteru Usui, Mariko Aso, Mitsuhiro Fukuda, Yukiko Toguchi, Hiroshi Suemune

Research output: Contribution to journalMeeting Abstract

Abstract

The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions by antitumor bleomycins (BLMs) and the acyclic keto aldehyde incorporated in DNA might react with DNA interacting biomolecules. We synthesized oligodeoxynuceotides 3-caged-1 and 3-caged-2 as caged precursors of 3, an ODN containing 1, to study the reactivities of 3 with amine. Irradiation of double stranded 3-caged-1 led to efficient formation of 3 compared to its single stranded form. Similarly, 3-caged-2 and its duplex afforded 3. With 3-caged-2, yields of 3 were lower compared to 3-caged-1. Formation of the duplex slowed decaging rate down but the yield of 3 was higher than that of single stranded 3-cage-2. Reaction of the obtained 3 with amine resulted in the formation of lactam 2b in good yield.

Original languageEnglish
Pages (from-to)33-34
Number of pages2
JournalNucleic acids symposium series (2004)
Issue number51
Publication statusPublished - Jan 1 2007

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Oligonucleotides
Amines
DNA
Lactams
Bleomycin
Aldehydes

All Science Journal Classification (ASJC) codes

  • Medicine(all)

Cite this

The photoreactivity of the caged precursors of oligonucleotides containing C4'-oxidized abasic site and reaction of the generated lesion. / Usui, Kazuteru; Aso, Mariko; Fukuda, Mitsuhiro; Toguchi, Yukiko; Suemune, Hiroshi.

In: Nucleic acids symposium series (2004), No. 51, 01.01.2007, p. 33-34.

Research output: Contribution to journalMeeting Abstract

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T1 - The photoreactivity of the caged precursors of oligonucleotides containing C4'-oxidized abasic site and reaction of the generated lesion.

AU - Usui, Kazuteru

AU - Aso, Mariko

AU - Fukuda, Mitsuhiro

AU - Toguchi, Yukiko

AU - Suemune, Hiroshi

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N2 - The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions by antitumor bleomycins (BLMs) and the acyclic keto aldehyde incorporated in DNA might react with DNA interacting biomolecules. We synthesized oligodeoxynuceotides 3-caged-1 and 3-caged-2 as caged precursors of 3, an ODN containing 1, to study the reactivities of 3 with amine. Irradiation of double stranded 3-caged-1 led to efficient formation of 3 compared to its single stranded form. Similarly, 3-caged-2 and its duplex afforded 3. With 3-caged-2, yields of 3 were lower compared to 3-caged-1. Formation of the duplex slowed decaging rate down but the yield of 3 was higher than that of single stranded 3-cage-2. Reaction of the obtained 3 with amine resulted in the formation of lactam 2b in good yield.

AB - The C4'-oxidized abasic site (1) is one of the oxidatively damaged DNA lesions by antitumor bleomycins (BLMs) and the acyclic keto aldehyde incorporated in DNA might react with DNA interacting biomolecules. We synthesized oligodeoxynuceotides 3-caged-1 and 3-caged-2 as caged precursors of 3, an ODN containing 1, to study the reactivities of 3 with amine. Irradiation of double stranded 3-caged-1 led to efficient formation of 3 compared to its single stranded form. Similarly, 3-caged-2 and its duplex afforded 3. With 3-caged-2, yields of 3 were lower compared to 3-caged-1. Formation of the duplex slowed decaging rate down but the yield of 3 was higher than that of single stranded 3-cage-2. Reaction of the obtained 3 with amine resulted in the formation of lactam 2b in good yield.

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