The DOI matches its Crossref record; 47 of the 47 references it cites were found in a registry or an index.
Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo
Open accessAbstract
Glycomics is emerging as a new field for the biology of complex glycoproteins and glycoconjugates. The lack of versatile glycan-labeling methods has presented a major obstacle to visualizing at the cellular level and studying glycoconjugates. To address this issue, we developed a fluorescent labeling technique based on the Cu(I)-catalyzed [3 + 2] cycloaddition, or click chemistry, which allows rapid, versatile, and specific covalent labeling of cellular glycans bearing azide groups. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl- N -ethyl-1,8-naphthalimide, by clicking the fluorescent trigger, the alkyne at the 4 position, with an azido-modified sugar. Using this click-activated fluorescent probe, we demonstrate incorporation of an azido-containing fucose analog into glycoproteins via the fucose salvage pathway. Distinct fluorescent signals were observed by flow cytometry when cells treated with 6-azidofucose were labeled with the click-activated fluorogenic probe or biotinylated alkyne. The intracellular localization of fucosylated glycoconjugates was visualized by using fluorescence microscopy. This technique will allow dynamic imaging of cellular fucosylation and facilitate studies of fucosylated glycoproteins and glycolipids.
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Cites
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Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis
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Cited by
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
Lutz, J.-F., & Zarafshani, Z. (2008) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2008.02.004 · Cited by 549
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Johnson, J. A., Finn, M. G., Koberstein, J. T., & Turro, N. J. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800208 · Cited by 320
Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells
Hsu, T.-L., Hanson, S. R., Kishikawa, K., Wang, S.-K., Sawa, M., & Wong, C.-H. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0611307104 · Cited by 319
Self-citation
Metadata
- Authors
- Sawa, M., Hsu, T.-L., Itoh, T., Sugiyama, M., Hanson, S. R., Vogt, P. K., & Wong, C.-H.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 2006-08-15
- Volume
- 103
- Issue
- 33
- Pages
- 12371-12376
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W4211031782
- Cited by
- 409
- References
- 47
- FWCI
- 17.15
- Type
- journal article
- Language
- en
- Open access
- green
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