Hybridization-Promoted and Cytidine-Selective Activation for Cross-Linking with the Use of 2-Amino-6-vinylpurine Derivatives

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) d...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-01, Vol.70 (1), p.14-23
Main Authors: Kawasaki, Takeshi, Nagatsugi, Fumi, Ali, Md. Monsur, Maeda, Minoru, Sugiyama, Kumiko, Hori, Kenji, Sasaki, Shigeki
Format: Article
Language:English
Subjects:
Base Pairing
Base Sequence
Biological and medical sciences
Cross-Linking Reagents - chemistry
Cytidine - chemistry
Drug Design
Fundamental and applied biological sciences. Psychology
Indicators and Reagents
Mechanisms. Catalysis. Electron transfer. Models
Molecular biophysics
Molecular Structure
Oligodeoxyribonucleotides - chemical synthesis
Oligodeoxyribonucleotides - chemistry
Physical chemistry in biology
Purines - chemistry
Sulfides
Vinyl Compounds - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048298p