The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
A General Method for Constraining Short Peptides to an α-Helical Conformation
Abstract
A method for constraining short peptides (<20 residues) of arbitrary sequence to an α-helical conformation (∼100% helical in H 2 O at 25 °C) is presented. Glutamine residues at positions i and i + 7 of the peptides were tethered with an alkanediyl chain between the side chain nitrogen atoms. Peptides containing this tether were readily synthesized on the solid phase by amide formation between an α,ω-diaminoalkane and the side chain carboxylates of glutamate residues. The resulting cyclic peptides were studied by NMR and CD and were found to adopt an α-helical conformation in aqueous solution. The α-helix was thermally stable to ≥40 °C. Corresponding untethered control peptides with N -methylglutamine at the i and i + 7 positions lacked helicity under the same conditions. Analogous peptides were also prepared for comparison using the thiolysine cross-linking method described previously [Jackson, D. Y.; King, D. S.; Chmielewski, J.; Singh, S.; Schultz, P. G. J. Am. Chem. Soc. 1991, 113, 9391−9392].
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Cites
Stabilization of alpha-helical structures in short peptides via end capping
Forood, B., Feliciano, E. J., & Nambiar, K. P. (1993) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.90.3.838 · Cited by 235
Chorev, M., Roubini, E., McKee, R. L., Gibbons, S. W., Goldman, M. E., Caulfield, M. P., & Rosenblatt, M. (1991) · Biochemistry · doi:10.1021/bi00238a022 · Cited by 107
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Schafmeister, C. E., Po, J., & Verdine, G. L. (2000) · Journal of the American Chemical Society · doi:10.1021/ja000563a · Cited by 1,037
Pelay‐Gimeno, M., Glas, A., Koch, O., & Grossmann, T. N. (2015) · Angewandte Chemie International Edition · doi:10.1002/anie.201412070 · Cited by 717
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Valeur, E., Guéret, S. M., Adihou, H., Gopalakrishnan, R., Lemurell, M., Waldmann, H., Grossmann, T. N., & Plowright, A. T. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201611914 · Cited by 382
Metadata
- Authors
- Phelan, J. C., Skelton, N. J., Braisted, A. C., & McDowell, R. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-01-01
- Volume
- 119
- Issue
- 3
- Pages
- 455-460
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2093715811
- Cited by
- 177
- References
- 2
- FWCI
- 2.02
- Type
- journal article
- Language
- en
- Open access
- closed
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- Phelan, J. C., Skelton, N. J., Braisted, A. C., & McDowell, R. S. (1997). A General Method for Constraining Short Peptides to an α-Helical Conformation. Journal of the American Chemical Society. https://doi.org/10.1021/ja9611654
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