Design, Synthesis, and Properties of 2‘,4‘-BNANC: A Bridged Nucleic Acid Analogue
datasetposted on 09.04.2008, 00:00 by S. M. Abdur Rahman, Sayori Seki, Satoshi Obika, Haruhisa Yoshikawa, Kazuyuki Miyashita, Takeshi Imanishi
Datasets usually provide raw data for analysis. This raw data often comes in spreadsheet form, but can be any collection of data, on which analysis can be performed.
The novel bridged nucleic-acid analogue 2‘,4‘-BNANC (2‘-O,4‘-C-aminomethylene bridged nucleic acid), containing a six-membered bridged structure with an N−O linkage, was designed and synthesized efficiently, demonstrating a one-pot intramolecular NC bond-forming key reaction to construct a perhydro-1,2-oxazine ring (11 and 12). Three monomers of 2‘,4‘-BNANC (2‘,4‘-BNANC[NH], [NMe], and [NBn]) were synthesized and incorporated into oligonucleotides, and their properties were investigated and compared with those of 2‘,4‘-BNA (LNA)-modified oligonucleotides. Compared to 2‘,4‘-BNA (LNA)-modified oligonucleotides, 2‘,4‘-BNANC congeners were found to possess: (i) equal or higher binding affinity against an RNA complement with excellent single-mismatch discriminating power, (ii) much better RNA selective binding, (iii) stronger and more sequence selective triplex-forming characters, and (iv) immensely higher nuclease resistance, even higher than the Sp-phosphorthioate analogue. 2‘,4‘-BNANC-modified oligonucleotides with these excellent profiles show great promise for applications in antisense and antigene technologies.