ArticleJournal of the American Chemical Society2013
n→π* interactions of amides and thioamides: implications for protein stability.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 66 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
66 citing papers in PubMed, 205 citations in OpenAlex.
- Thioimidate Protection Enables Amide, Thioamide, and Amidine Installation at Aspartic Acid Residues.The Journal of organic chemistry · 2026Article
- Backbone double-mutant cycle analysis quantifies hydrogen-bond energies in proteins.Protein science : a publication of the Protein Society · 2026Article
- The interplay between the pyramidalization of carbonyl carbons and the n → π* interactions in biomolecules.Protein science : a publication of the Protein Society · 2026Article
- Stereoelectronic and hydrogen-bonding effects on hydroxyproline conformation.Communications chemistry · 2026Article
- Assessment of Energy Effects DeterminingACS physical chemistry Au · 2026Article
- HalogenatedRSC advances · 2025Article
- Thioamides in C5 Hydrogen Bonds: Implications for Protein β-Strands.The Journal of organic chemistry · 2025Article
- Pauli Exclusion by n→π* Interactions: Implications for Paleobiology.ACS central science · 2024Article
- Complementary Strategies for Installation of Thioimidates into Peptide Backbones.The Journal of organic chemistry · 2024Article
- The Development of CDC25A-Derived Phosphoseryl Peptides That Bind 14-3-3ε with High Affinities.International journal of molecular sciences · 2024Article
- Probing Non-Covalent Interactions through Molecular Balances: A REG-IQA Study.Molecules (Basel, Switzerland) · 2024Article
- Thioimidate Solutions to Thioamide Problems during Thionopeptide Deprotection.Organic letters · 2024Article
- Thioimidates provide general access to thioamide, amidine, and imidazolone peptide-bond isosteres.Methods in enzymology · 2024Article
- Thioamide Analogues of MHC I Antigen Peptides.Journal of the American Chemical Society · 2023Article
- Molecular orbital and topological electron density study of n → π* interactions: amides and thioamides cases.RSC advances · 2023Article
- Quantifying Amide-Aromatic Interactions at Molecular and Atomic Levels: Experimentally-determined Enthalpic and Entropic Contributions to Interactions of Amide spbioRxiv : the preprint server for biology · 2023Article
- The Realm of Unconventional Noncovalent Interactions in Proteins: Their Significance in Structure and Function.ACS omega · 2023Review
- A molecular descriptor of intramolecular noncovalent interaction for regulating optoelectronic properties of organic semiconductors.Nature communications · 2023Article
- Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles.Chemical science · 2023Article
- Intermolecular noncovalent interactions with carbon in solution.Chemical science · 2022Article
6 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
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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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.