Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

Shuhei Kusano; Tomoya Sakuraba; Shinya Hagihara; Fumi Nagatsugi

doi:10.1016/j.bmcl.2012.08.122

Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

Shuhei Kusano, Tomoya Sakuraba, Shinya Hagihara, Fumi Nagatsugi

Division of Organic- and Biomaterials Research

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

2 Citations (Scopus)

Abstract

Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity.

Original language	English
Pages (from-to)	6957-6961
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2012.08.122
Publication status	Published - 2012 Nov 15

Keywords

Antisense
Cross-linking
Oligonucleotides
Purine derivatives
miRNA

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2012.08.122

Cite this

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title = "Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity",

abstract = "Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity.",

keywords = "Antisense, Cross-linking, Oligonucleotides, Purine derivatives, miRNA",

author = "Shuhei Kusano and Tomoya Sakuraba and Shinya Hagihara and Fumi Nagatsugi",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) and (S) from Japan Society for the Promotion of Science (JSPS), CREST from Japan Science and Technology Agency. ",

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doi = "10.1016/j.bmcl.2012.08.122",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

AU - Kusano, Shuhei

AU - Sakuraba, Tomoya

AU - Hagihara, Shinya

AU - Nagatsugi, Fumi

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) and (S) from Japan Society for the Promotion of Science (JSPS), CREST from Japan Science and Technology Agency.

PY - 2012/11/15

Y1 - 2012/11/15

N2 - Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity.

AB - Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity.

KW - Antisense

KW - Cross-linking

KW - Oligonucleotides

KW - Purine derivatives

KW - miRNA

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DO - 10.1016/j.bmcl.2012.08.122

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JO - Bioorganic and Medicinal Chemistry Letters

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Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

Abstract

Keywords

ASJC Scopus subject areas

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