Hybridization-promoted and cytidine-selective activation for cross-linking with the use of 2-amino-6-vinylpurine derivatives

Takeshi Kawasaki, Fumi Nagatsugi, Md Monsur Ali, Minoru Maeda, Kumiko Sugiyama, Kenji Hori, Shigeki Sasaki

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

(Chemical Equation Presented). Recently, we have proposed a new concept for cross-linking agents with inducible reactivity, in which the highly reactive cross-linking agent, the 2-amino-6-vinylpurine nucleoside analogue (1), can be regenerated in situ from its stable precursors, the phenylsulfide (4) and the phenylsulfoxide (3) derivatives, by a hybridization-promoted activation process with selectivity to cytidine. The phenylsulfide precursor (4) exhibited cross-linking ability despite its high stability toward strong nucleophiles such as amines and thiols. In this study, we investigated the substituent effects of the phenylsulfide group on the cross-linking reaction, and determined the 2-carboxy substituent of the phenylsulfide derivative (11k) as an efficient cross-linking agent with inducible reactivity. Detailed investigations have shown that the phenylsulfoxide (3) and phenylsulfide (4) precursors produce the 2-amino-6-vinylpurine nucleoside (1) as the common reactive species. It has been concluded that the nature of the inducible reactivity of the precursors (3 and 4) is acceleration of their elimination to the 2-amino-6-vinylpurine nucleoside (1) through the selective process in the duplex with the ODN having cytidine at the target site.

Original languageEnglish
Pages (from-to)14-23
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number1
DOIs
Publication statusPublished - Jan 7 2005

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Cytidine
Nucleosides
Chemical activation
Derivatives
Nucleophiles
Sulfhydryl Compounds
Amines
2-amino-6-vinylpurine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Hybridization-promoted and cytidine-selective activation for cross-linking with the use of 2-amino-6-vinylpurine derivatives. / Kawasaki, Takeshi; Nagatsugi, Fumi; Ali, Md Monsur; Maeda, Minoru; Sugiyama, Kumiko; Hori, Kenji; Sasaki, Shigeki.

In: Journal of Organic Chemistry, Vol. 70, No. 1, 07.01.2005, p. 14-23.

Research output: Contribution to journalArticle

Kawasaki, Takeshi ; Nagatsugi, Fumi ; Ali, Md Monsur ; Maeda, Minoru ; Sugiyama, Kumiko ; Hori, Kenji ; Sasaki, Shigeki. / Hybridization-promoted and cytidine-selective activation for cross-linking with the use of 2-amino-6-vinylpurine derivatives. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 1. pp. 14-23.
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