Design, synthesis, and properties of 2′,4′-BNANC: A bridged nucleic acid analogue

被引：0

作者：

Rahman, S. M. Abdur ^{[1
,3
]}

Seki, Sayori ^{[1
]}

Obika, Satoshi ^{[1
,2
]}

Yoshikawa, Haruhisa ^{[1
]}

Miyashita, Kazuyuki ^{[1
]}

Imanishi, Takeshi ^{[1
]}

机构：

[1] Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan

[2] PRESTO, JST, Sanbancho Building, 5-Sanbancho, Chiyodaku, Tokyo 102-0075, Japan

[3] Faculty of Pharmacy, University of Dhaka

来源：

Journal of the American Chemical Society | 2008年 / 130卷 / 14期

关键词：

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. © 2008 American Chemical Society;

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摘要：

Journal article (JA)

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页码：4886 / 4896