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A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry
Open accessAbstract
Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4-yne (DIMAC). Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection.
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Dieterich, D. C., Link, A. J., Graumann, J., Tirrell, D. A., & Schuman, E. M. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0601637103 · Cited by 874
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Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality
Sletten, E. M., & Bertozzi, C. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200900942 · Cited by 3,165
Self-citationCu-free click cycloaddition reactions in chemical biology
Jewett, J. C., & Bertozzi, C. R. (2010) · Chemical Society Reviews · doi:10.1039/b901970g · Cited by 1,684
Self-citationRapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones
Jewett, J. C., Sletten, E. M., & Bertozzi, C. R. (2010) · Journal of the American Chemical Society · doi:10.1021/ja100014q · Cited by 697
Self-citationAza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition
Debets, M. F., van Berkel, S. S., Schoffelen, S., Rutjes, F. P. J. T., van Hest, J. C. M., & van Delft, F. L. (2010) · Chem. Commun. · doi:10.1039/b917797c · Cited by 580
An overview of injectable polymeric hydrogels for tissue engineering
Sivashanmugam, A., Arun Kumar, R., Vishnu Priya, M., Nair, S. V., & Jayakumar, R. (2015) · European Polymer Journal · doi:10.1016/j.eurpolymj.2015.05.014 · Cited by 366
Metadata
- Authors
- Sletten, E. M., & Bertozzi, C. R.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-06-13
- Volume
- 10
- Issue
- 14
- Pages
- 3097-3099
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2087171377
- Cited by
- 296
- References
- 1
- FWCI
- 14.03
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Sletten, E. M., & Bertozzi, C. R. (2008). A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry. Organic Letters. https://doi.org/10.1021/ol801141k
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.