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Click Chemistry as a Route to Cyclic Tetrapeptide Analogues: Synthesis of cyclo-[Pro-Val-ψ(triazole)-Pro-Tyr]
Abstract
Despite the plethora of techniques to cyclize small peptides, a synthesis of cyclo-[(L)Pro-(L)Tyr-(L)Pro-(L)Val], a potent tyrosinase inhibitor, remains elusive because of the unfavorable transition state leading to the cyclic product. Herein, we report the successful synthesis of its triazole analogue, cyclo-[(L)Pro-(L)Val-psi(triazole)-(L)Pro-(L)Tyr]. Attempted cyclization via peptide bond formation at room temperature fails to provide the desired product, but Cu(I)-catalyzed alkyne-azide coupling at 110 degrees C affords the triazole tetrapeptide in 70% yield, demonstrating the utility of "click" chemistry.
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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
Cited by
Cu-Catalyzed Azide−Alkyne Cycloaddition
Meldal, M., & Tornøe, C. W. (2008) · Chemical Reviews · doi:10.1021/cr0783479 · Cited by 4,628
Contemporary strategies for peptide macrocyclization
White, C. J., & Yudin, A. K. (2011) · Nature Chemistry · doi:10.1038/nchem.1062 · Cited by 1,088
Lutz, J.-F., & Zarafshani, Z. (2008) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2008.02.004 · Cited by 549
Bock, V. D., Speijer, D., Hiemstra, H., & van Maarseveen, J. H. (2007) · Organic & Biomolecular Chemistry · doi:10.1039/b616751a · Cited by 287
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Metadata
- Authors
- Bock, V. D., Perciaccante, R., Jansen, T. P., Hiemstra, H., & van Maarseveen, J. H.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-02-08
- Volume
- 8
- Issue
- 5
- Pages
- 919-922
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2048394663
- Cited by
- 196
- References
- 1
- FWCI
- 10.57
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bock, V. D., Perciaccante, R., Jansen, T. P., Hiemstra, H., & van Maarseveen, J. H. (2006). Click Chemistry as a Route to Cyclic Tetrapeptide Analogues: Synthesis of cyclo-[Pro-Val-ψ(triazole)-Pro-Tyr]. Organic Letters. https://doi.org/10.1021/ol053095o
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