Straightforward Synthesis of Purine 4鈥?Alkoxy-2鈥?deoxynucleosides: First Report of Mixed Purine鈥揚yrimidine 4鈥?Alkoxyoligodeoxynucleotides as New RNA Mimics
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- 作者：Magdalena Petrov谩 ; Ond艡ej P谩v ; Milo拧 Bud臎拧铆nsk媒 ; Eva Zborn铆kov谩 ; Pavel Nov谩k ; 艩谩rka Rosenbergov谩 ; Ond艡ej Pa膷es ; Radek Liboska ; Ivana Dvo艡谩kov谩 ; Ond艡ej 艩im谩k ; Ivan Rosenberg
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：July 17, 2015
- 年：2015
- 卷：17
- 期：14
- 页码：3426-3429
- 全文大小：328K
- ISSN：1523-7052
文摘
Purine and pyrimidine 4鈥?alkoxy-2鈥?deoxynucleosides were efficiently prepared from nucleoside 4鈥?5鈥?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鈥?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鈥?alkoxy-oligodeoxynucleotides in antisense technologies.