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Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure
Open accessAbstract
We have synthesized and characterized a family of structured oligo-N-substituted-glycines (peptoids) up to 36 residues in length by using an efficient solid-phase protocol to incorporate chemically diverse side chains in a sequence-specific fashion. We investigated polypeptoids containing side chains with a chiral center adjacent to the main chain nitrogen. Some of these sequences have stable secondary structure, despite the achirality of the polymer backbone and its lack of hydrogen bond donors. In both aqueous and organic solvents, peptoid oligomers as short as five residues give rise to CD spectra that strongly resemble those of peptide α-helices. Differential scanning calorimetry and CD measurements show that polypeptoid secondary structure is highly stable and that unfolding is reversible and cooperative. Thermodynamic parameters obtained for unfolding are similar to those obtained for the α-helix to coil transitions of peptides. This class of biomimetic polymers may enable the design of self-assembling macromolecules with novel structures and functions.
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Cited by
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Nakano, T., & Okamoto, Y. (2001) · Chemical Reviews · doi:10.1021/cr0000978 · Cited by 1,375
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Das, R., & Baker, D. (2008) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.77.062906.171838 · Cited by 989
Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides
Chongsiriwatana, N. P., Patch, J. A., Czyzewski, A. M., Dohm, M. T., Ivankin, A., Gidalevitz, D., Zuckermann, R. N., & Barron, A. E. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0708254105 · Cited by 657
Self-citationFree-floating ultrathin two-dimensional crystals from sequence-specific peptoid polymers
Nam, K. T., Shelby, S. A., Choi, P. H., Marciel, A. B., Chen, R., Tan, L., Chu, T. K., Mesch, R. A., Lee, B.-C., Connolly, M. D., et al. (2010) · Nature Materials · doi:10.1038/nmat2742 · Cited by 417
Self-citationNew Peptidomimetic Polymers for Antifouling Surfaces
Statz, A. R., Meagher, R. J., Barron, A. E., & Messersmith, P. B. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0522534 · Cited by 409
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Metadata
- Authors
- Kirshenbaum, K., Barron, A. E., Goldsmith, R. A., Armand, P., Bradley, E. K., Truong, K. T. V., Dill, K. A., Cohen, F. E., & Zuckermann, R. N.
- Venue
- Proceedings of the National Academy of Sciences
- Published
- 1998-04-14
- Volume
- 95
- Issue
- 8
- Pages
- 4303-4308
- ISSN
- 0027-8424 (ISSN-L)
- 1091-6490
- OpenAlex
- W2091332750
- Cited by
- 483
- References
- 0
- FWCI
- 4.95
- Type
- journal article
- Language
- en
- Open access
- green
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- Kirshenbaum, K., Barron, A. E., Goldsmith, R. A., Armand, P., Bradley, E. K., Truong, K. T. V., Dill, K. A., Cohen, F. E., & Zuckermann, R. N. (1998). Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.95.8.4303
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