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Click Chemistry as a Reliable Method for the High-Density Postsynthetic Functionalization of Alkyne-Modified DNA
Abstract
[reaction: see text] We report the development of the Cu(I)-catalyzed Huisgen cycloaddition (click) reaction for the multiple postsynthetic labeling of alkyne-modified DNA. A series of alkyne-modified oligodeoxyribonucleotides (ODNs) of increasing alkyne density were prepared, and the click reaction using various azide labels was investigated. Complete high-density conversion was observed for ODNs containing up to six consecutive alkyne functions. Compatibility of the click conditions with long DNA strands was shown using a PCR product obtained with an alkyne-modified primer.
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Citations
Cites
Oxidative Nucleobase Modifications Leading to Strand Scission
Burrows, C. J., & Muller, J. G. (1998) · Chemical Reviews · doi:10.1021/cr960421s · Cited by 1,736
Cited by
The growing applications of click chemistry
Moses, J. E., & Moorhouse, A. D. (2007) · Chem. Soc. Rev. · doi:10.1039/b613014n · Cited by 2,367
Click Chemistry: 1,2,3‐Triazoles as Pharmacophores
Agalave, S. G., Maujan, S. R., & Pore, V. S. (2011) · Chemistry – An Asian Journal · doi:10.1002/asia.201100432 · Cited by 1,305
Medicinal attributes of 1,2,3-triazoles: Current developments
Dheer, D., Singh, V., & Shankar, R. (2017) · Bioorganic Chemistry · doi:10.1016/j.bioorg.2017.01.010 · Cited by 873
Dommerholt, J., Schmidt, S., Temming, R., Hendriks, L. J. A., Rutjes, F. P. J. T., van Hest, J. C. M., Lefeber, D. J., Friedl, P., & van Delft, F. L. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201003761 · Cited by 720
“Click”‐Chemistry in Polymer and Material Science: the Update
Binder, W. H. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800332 · Cited by 567
Metadata
- Authors
- Gierlich, J., Burley, G. A., Gramlich, P. M. E., Hammond, D. M., & Carell, T.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-07-21
- Volume
- 8
- Issue
- 17
- Pages
- 3639-3642
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2027086637
- Cited by
- 492
- References
- 1
- FWCI
- 18.94
- Type
- journal article
- Language
- en
- Open access
- closed
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