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Synthesis and Properties of Oligonucleotides Containing 5-Substituted Pyrimidine Nucleoside
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- Ozaki Hiroaki
- Department of Chemistry, Gunma University
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- Kuwahara Masayasu
- Department of Chemistry, Gunma University
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- Sawai Hiroaki
- Department of Chemistry, Gunma University
Bibliographic Information
- Other Title
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- 5位置換ピリミジンヌクレオシドを含むオリゴヌクレオチドの合成とその性質
- 5イ チカン ピリミジンヌクレオシド オ フクム オリゴヌクレオチド ノ ゴウセイ ト ソノ セイシツ
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Description
Our recent study on the oligodeoxyribonucleotide (ODN) containing 5-substituted pyrimidine nucleosides is described. 5-Substituted 2 '-deoxyuridine derivatives and 5-substituted arabinofuranosyluracil derivatives were synthesized from 2, 2 '-anhydro-5-methoxycarbonylmethyluridine, which was synthesized from arabinoaminooxazoline and dimethyl α-bromomethylfumarate. Modified ODNs bearing these nucleoside analogs were prepared chemically by pre-synthetic modification method or post-synthetic modification method. Effect of 5-substituent groups on DNA/DNA or DNA/RNA duplexes was investigated by measuring the melting behaviors. Some of these modified ODNs are expected as antisense ODNs since these could induce RNase H activity and impart stability against nuclease. Also, 5-substituted 2 '-deoxyuridine analog triphosphates served as substrates of thermophilic family B DNA polymerases in a primer extension reaction or PCR, to give the modified ODNs. 5-Methoxycarbonylmethy1-2'-deoxyuridine residues incorporated into DNA by PCR could be used to post-synthetic derivatization. This finding is useful for in vitro selection of the functionalized DNA.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 62 (12), 1238-1248, 2004
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680289885568
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- NII Article ID
- 10014119789
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 7179554
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- Text Lang
- ja
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- Article Type
- journal article
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- Data Source
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- JaLC
- NDL Search
- Crossref
- CiNii Articles
- KAKEN
- OpenAIRE
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- Abstract License Flag
- Disallowed