The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Design, Synthesis, and Properties of 2‘,4‘-BNANC: A Bridged Nucleic Acid Analogue
Abstract
The novel bridged nucleic-acid analogue 2',4'-BNA(NC) (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'-BNA(NC) (2',4'-BNA(NC)[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'-BNA(NC) 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 S(p)-phosphorthioate analogue. 2',4'-BNA(NC)-modified oligonucleotides with these excellent profiles show great promise for applications in antisense and antigene technologies.
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Cites
Progress in antisense technology
Crooke, S. T. (2004) · Annual Review of Medicine · doi:10.1146/annurev.med.55.091902.104408 · Cited by 417
Cited by
The Medicinal Chemistry of Therapeutic Oligonucleotides
Wan, W. B., & Seth, P. P. (2016) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.6b00551 · Cited by 429
Recent progress in non-native nucleic acid modifications
McKenzie, L. K., El-Khoury, R., Thorpe, J. D., Damha, M. J., & Hollenstein, M. (2021) · Chemical Society Reviews · doi:10.1039/d0cs01430c · Cited by 300
Incorporation of bridged nucleic acids into CRISPR RNAs improves Cas9 endonuclease specificity
Cromwell, C. R., Sung, K., Park, J., Krysler, A. R., Jovel, J., Kim, S. K., & Hubbard, B. P. (2018) · Nature Communications · doi:10.1038/s41467-018-03927-0 · Cited by 190
Metadata
- Authors
- Abdur Rahman, S. M., Seki, S., Obika, S., Yoshikawa, H., Miyashita, K., & Imanishi, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-03-15
- Volume
- 130
- Issue
- 14
- Pages
- 4886-4896
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1987578671
- Cited by
- 163
- References
- 1
- FWCI
- 6.82
- Type
- journal article
- Language
- en
- Open access
- closed
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