The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Chemoselective Formation of Successive Triazole Linkages in One Pot: “Click−Click” Chemistry
Abstract
A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical "click" chemistry.
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Citations
Cites
Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
“Click”‐Chemistry in Polymer and Material Science: the Update
Binder, W. H. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800332 · Cited by 567
Postsynthetic DNA Modification through the Copper‐Catalyzed Azide–Alkyne Cycloaddition Reaction
Gramlich, P. M. E., Wirges, C. T., Manetto, A., & Carell, T. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802077 · Cited by 406
Metal chelating systems synthesized using the copper(i) catalyzed azide-alkynecycloaddition
Struthers, H., Mindt, T. L., & Schibli, R. (2010) · Dalton Trans. · doi:10.1039/b912608b · Cited by 386
Johnson, J. A., Finn, M. G., Koberstein, J. T., & Turro, N. J. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800208 · Cited by 320
van Dijk, M., Rijkers, D. T. S., Liskamp, R. M. J., van Nostrum, C. F., & Hennink, W. E. (2009) · Bioconjugate Chemistry · doi:10.1021/bc900087a · Cited by 300
Metadata
- Authors
- Aucagne, V., & Leigh, D. A.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-09-01
- Volume
- 8
- Issue
- 20
- Pages
- 4505-4507
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W1991446381
- Cited by
- 220
- References
- 1
- FWCI
- 10.37
- Type
- journal article
- Language
- en
- Open access
- closed
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