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A Heterocyclic Peptide Nanotube
Abstract
An open-ended hollow tubular structure is designed based on hydrogen-bond-directed self-assembly of a chimeric cyclic peptide subunit comprised of alternating alpha- and epsilon-amino acids. The design features a novel 1,4-disubstituted-1,2,3-triazole epsilon-amino acid and its utility as a peptide backbone substitute. The N-Fmoc-protected epsilon-amino acid was synthesized in high yield and optical purity in three steps from readily available starting materials and was employed in solid-phase peptide synthesis to afford the desired cyclic peptide structure. The cyclic peptide self-assembly has been studied in solution by (1)H NMR and mass spectrometry and the resulting tubular ensemble characterized in the solid state by X-ray crystallography.
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
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
Contemporary strategies for peptide macrocyclization
White, C. J., & Yudin, A. K. (2011) · Nature Chemistry · doi:10.1038/nchem.1062 · Cited by 1,088
“Click”‐Chemistry in Polymer and Material Science: the Update
Binder, W. H. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800332 · Cited by 567
Zhang, Y., Yuan, S., Liu, P., Jing, L., Pan, H., Ren, X.-K., & Chen, Z. (2021) · Organic Chemistry Frontiers · doi:10.1039/d1qo00520k · Cited by 58
Metadata
- Authors
- Horne, W. S., Stout, C. D., & Ghadiri, M. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-07-09
- Volume
- 125
- Issue
- 31
- Pages
- 9372-9376
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2089455498
- Cited by
- 317
- References
- 1
- FWCI
- 8.87
- Type
- journal article
- Language
- en
- Open access
- closed
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