The DOI matches its Crossref record; 43 of the 43 references it cites were found in a registry or an index.
Tricks with clicks: modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition
Abstract
This tutorial review examines recent developments involving use of Copper-catalyzed Azide-Alkyne [3 + 2] Cycloaddition (CuAAC) reactions in the synthesis, modification, and conformational control of peptidomimetic oligomers. CuAAC reactions have been used to address a variety of objectives including: (i) ligation of peptidomimetic oligomers; (ii) synthesis of ordered "foldamer" architectures; (iii) conjugation of ligands to peptidomimetic scaffolds; and (iv) macrocyclization of peptidomimetics using triazole linkages as conformational constraints. Variations in synthesis protocols, such as the use of different solvent systems, temperatures and copper species are evaluated herein to present a range of variables for the optimization of CuAAC reactions. The overall objectives of these studies are assessed to highlight the widespread applications of the products, which range from bioactive ligands to new materials.
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Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cu-Catalyzed Azide−Alkyne Cycloaddition
Meldal, M., & Tornøe, C. W. (2008) · Chemical Reviews · doi:10.1021/cr0783479 · Cited by 4,628
Taking advantage of luminescent lanthanide ions
Bünzli, J.-C. G., & Piguet, C. (2005) · Chemical Society Reviews · doi:10.1039/b406082m · Cited by 3,797
The growing impact of click chemistry on drug discovery
Kolb, H. C., & Sharpless, K. B. (2003) · Drug Discovery Today · doi:10.1016/s1359-6446(03)02933-7 · Cited by 3,148
The growing applications of click chemistry
Moses, J. E., & Moorhouse, A. D. (2007) · Chem. Soc. Rev. · doi:10.1039/b613014n · Cited by 2,367
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides
Zhang, L., Chen, X., Xue, P., Sun, H. H. Y., Williams, I. D., Sharpless, K. B., Fokin, V. V., & Jia, G. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054114s · Cited by 1,120
The Emergence of Thiol–Ene Coupling as a Click Process for Materials and Bioorganic Chemistry
Dondoni, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802516 · Cited by 619
Peptidomimetics via copper-catalyzed azide–alkyne cycloadditions
Angell, Y. L., & Burgess, K. (2007) · Chemical Society Reviews · doi:10.1039/b701444a · Cited by 589
Heterocyclic Peptide Backbone Modifications in an α-Helical Coiled Coil
Horne, W. S., Yadav, M. K., Stout, C. D., & Ghadiri, M. R. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0450408 · Cited by 475
Cited by
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
Metadata
- Authors
- Holub, J. M., & Kirshenbaum, K.
- Venue
- Chemical Society Reviews
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2010
- Volume
- 39
- Issue
- 4
- Pages
- 1325
- ISSN
- 0306-0012 (ISSN-L)
- 1460-4744
- OpenAlex
- W2067136873
- Cited by
- 326
- References
- 43
- FWCI
- 1.55
- Type
- journal article
- Language
- en
- Open access
- closed
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- Holub, J. M., & Kirshenbaum, K. (2010). Tricks with clicks: modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. Chemical Society Reviews. https://doi.org/10.1039/b901977b
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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