Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue.

Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue. Research Abstract Details 

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Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue. Abstract Text:

S M Abdur Rahman,Sayori Seki,Satoshi Obika,Haruhisa Yoshikawa,Kazuyuki Miyashita,Takeshi Imanishi,S M Abdur Rahman,Sayori Seki,Satoshi Obika,Haruhisa Yoshikawa,Kazuyuki Miyashita,Takeshi Imanishi,

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.

Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue. Publishing Authors By Initials

SM Rahman,S Seki,S Obika,H Yoshikawa,K Miyashita,T Imanishi,SM Rahman,S Seki,S Obika,H Yoshikawa,K Miyashita,T Imanishi,

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Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 130

Page Numbers: 4886-96

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 1520-5126

DAY: 15

MONTH: 03

YEAR: 2008

Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

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Grant and Affiliation Information for Design, Synthesis, and Properties of 2',4'-BNA(NC): A Bridged Nucleic Acid Analogue.

AFFILIATION: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan, and PRESTO, JST, Sanbancho Building, 5-Sanbancho, Chiyodaku, Tokyo 102-0075, Japan.

Country: United States

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MEDLINETA: J Am Chem Soc

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