Straightforward Synthesis of Purine 4'-Alkoxy-2'-deoxynucleosides: First Report of Mixed Purine-Pyrimidine 4'-Alkoxyoligodeoxynucleotides as New RNA Mimics
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- antisense oligonukleotidy chemie MeSH
- hybridizace nukleových kyselin MeSH
- konformace nukleové kyseliny MeSH
- molekulární konformace MeSH
- molekulární struktura MeSH
- oligodeoxyribonukleotidy chemická syntéza chemie MeSH
- puriny chemie MeSH
- RNA chemie MeSH
- sukcinimidy chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- antisense oligonukleotidy MeSH
- N-iodosuccinimide MeSH Prohlížeč
- oligodeoxyribonukleotidy MeSH
- purine MeSH Prohlížeč
- puriny MeSH
- RNA MeSH
- sukcinimidy 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.
Citace poskytuje Crossref.org
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