2'-O,4'-C-methyleneoxymethylene bridged nucleic acids (2',4'-BNA(COC))

Yoshiyuki Hari; Tetsuya Kodama; Takeshi Imanishi; Satoshi Obika

doi:10.1007/978-1-61779-188-8_3

2'-O,4'-C-methyleneoxymethylene bridged nucleic acids (2',4'-BNA(COC))

Methods Mol Biol. 2011:764:31-57. doi: 10.1007/978-1-61779-188-8_3.

Authors

Yoshiyuki Hari¹, Tetsuya Kodama, Takeshi Imanishi, Satoshi Obika

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. hari@phs.osaka-u.ac.jp

PMID: 21748632
DOI: 10.1007/978-1-61779-188-8_3

Abstract

The synthesis of 2'-O,4'-C-methyleneoxymethylene bridged nucleoside (2',4'-BNA(COC)) phosphoramidites and oligonucleotides containing 2',4'-BNA(COC) are described. 2',4'-BNA(COC) phosphoramidites bearing natural nucleobases, such as thymine, cytosine, 5-methylcytosine, adenine, and guanine were synthesized. Moreover, fully or partially 2',4'-BNA(COC)-modified oligonucleotides can be prepared by using a standard protocol except for a prolonged coupling time on an automated DNA synthesizer.

MeSH terms

5-Methylcytosine / analogs & derivatives
Adenine / analogs & derivatives
Biological Products / chemical synthesis*
Bridged-Ring Compounds / chemical synthesis*
Chemistry, Pharmaceutical / methods*
Cytosine / analogs & derivatives
DNA / chemistry
DNA / metabolism
Guanine / analogs & derivatives
Nucleosides / chemistry
Oligonucleotides / chemical synthesis*
Oligonucleotides, Antisense / chemical synthesis*
Organophosphorus Compounds / chemical synthesis*
RNA / chemistry
RNA / metabolism
Thymine / analogs & derivatives

Substances

Biological Products
Bridged-Ring Compounds
Nucleosides
Oligonucleotides
Oligonucleotides, Antisense
Organophosphorus Compounds
phosphoramidite
Guanine
RNA
5-Methylcytosine
Cytosine
DNA
Adenine
Thymine