Straightforward Synthesis of Purine 4'-Alkoxy-2'-deoxynucleosides: First Report of Mixed Purine-Pyrimidine 4'-Alkoxyoligodeoxynucleotides as New RNA Mimics
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- Oligonucleotides, Antisense chemistry MeSH
- Nucleic Acid Hybridization MeSH
- Nucleic Acid Conformation MeSH
- Molecular Conformation MeSH
- Molecular Structure MeSH
- Oligodeoxyribonucleotides chemical synthesis chemistry MeSH
- Purines chemistry MeSH
- RNA chemistry MeSH
- Succinimides chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Oligonucleotides, Antisense MeSH
- N-iodosuccinimide MeSH Browser
- Oligodeoxyribonucleotides MeSH
- purine MeSH Browser
- Purines MeSH
- RNA MeSH
- Succinimides MeSH
Purine and pyrimidine 4'-alkoxy-2'-deoxynucleosides were efficiently prepared from nucleoside 4'-5'-enol acetates in three steps by N-iodosuccinimide promoted alkoxylation, hydrolysis, and reduction followed by conversion to phosphoramidite monomers for the solid-phase synthesis of the oligonucleotides. Fully modified 4'-alkoxyoligodeoxynucleotides, which are characterized by a prevalent N-type (RNA-like) conformation, exhibited superior chemical and nuclease resistance as well as excellent hybridization properties with a strong tendency for RNA-selective hybridization, suggesting a potential application of 4'-alkoxy-oligodeoxynucleotides in antisense technologies.
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