The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
n→π* Interactions of Amides and Thioamides: Implications for Protein Stability
Open accessAbstract
Carbonyl-carbonyl interactions between adjacent backbone amides have been implicated in the conformational stability of proteins. By combining experimental and computational approaches, we show that relevant amidic carbonyl groups associate through an n→π* donor-acceptor interaction with an energy of at least 0.27 kcal/mol. The n→π* interaction between two thioamides is 3-fold stronger than between two oxoamides due to increased overlap and reduced energy difference between the donor and acceptor orbitals. This result suggests that backbone thioamide incorporation could stabilize protein structures. Finally, we demonstrate that intimate carbonyl interactions are described more completely as donor-acceptor orbital interactions rather than dipole-dipole interactions.
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Cites
Principles that Govern the Folding of Protein Chains
Anfinsen, C. B. (1973) · Science · doi:10.1126/science.181.4096.223 · Cited by 7,096
Collagen Structure and Stability
Shoulders, M. D., & Raines, R. T. (2009) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.77.032207.120833 · Cited by 3,923
Self-citationRationalization of the effects of mutations on peptide andprotein aggregation rates
Chiti, F., Stefani, M., Taddei, N., Ramponi, G., & Dobson, C. M. (2003) · Nature · doi:10.1038/nature01891 · Cited by 1,072
Cited by
A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design
Beno, B. R., Yeung, K.-S., Bartberger, M. D., Pennington, L. D., & Meanwell, N. A. (2015) · Journal of Medicinal Chemistry · doi:10.1021/jm501853m · Cited by 772
Biosynthesis and Chemical Applications of Thioamides
Mahanta, N., Szantai-Kis, D. M., Petersson, E. J., & Mitchell, D. A. (2019) · ACS Chemical Biology · doi:10.1021/acschembio.8b01022 · Cited by 218
Thioamide Analogues of MHC I Antigen Peptides
Gibadullin, R., Morris, R. K., Niu, J., Sidney, J., Sette, A., & Gellman, S. H. (2023) · Journal of the American Chemical Society · doi:10.1021/jacs.3c05300 · Cited by 17
Architectonic principles of polyproline II helix bundle protein domains
Rodríguez, C. S., & Laurents, D. V. (2024) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2024.109981 · Cited by 9
Metadata
- Authors
- Newberry, R. W., VanVeller, B., Guzei, I. A., & Raines, R. T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-05-20
- Volume
- 135
- Issue
- 21
- Pages
- 7843-7846
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1969697060
- Cited by
- 210
- References
- 3
- FWCI
- 11.45
- Type
- journal article
- Language
- en
- Open access
- hybrid
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