ArticleJournal of the American Chemical Society2012
Using thioamides to site-specifically interrogate the dynamics of hydrogen bond formation in β-sheet folding.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Thioimidate Protection Enables Amide, Thioamide, and Amidine Installation at Aspartic Acid Residues.The Journal of organic chemistry · 2026Article
- Thioamides in C5 Hydrogen Bonds: Implications for Protein β-Strands.The Journal of organic chemistry · 2025Article
- Complementary Strategies for Installation of Thioimidates into Peptide Backbones.The Journal of organic chemistry · 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
- Structural impact of thioamide incorporation into a β-hairpin.RSC chemical biology · 2022Article
- Hydrogen Bond and Geometry Effects of Thioamide Backbone Modifications.The Journal of organic chemistry · 2021Article
- Comparing C2=O and C2=S Barbiturates: Different Hydrogen-Bonding Patterns of Thiobarbiturates in Solution and the Solid State.International journal of molecular sciences · 2021Article
- Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions.Journal of the American Chemical Society · 2021Article
- Increasing protein stability by engineering the n → π* interaction at the β-turn.Chemical science · 2020Article
- Biosynthesis and Chemical Applications of Thioamides.ACS chemical biology · 2019Review
- Thioamide substitution to probe the hydroxyproline recognition of VHL ligands.Bioorganic & medicinal chemistry · 2018Article
- Protein stabilization by tuning the steric restraint at the reverse turn.Chemical science · 2018Article
- Dithioamide substitutions in proteins: effects on thermostability, peptide binding, and fluorescence quenching in calmodulin.Chemical communications (Cambridge, England) · 2018Article
- Thioamide Substitution Selectively Modulates Proteolysis and Receptor Activity of Therapeutic Peptide Hormones.Journal of the American Chemical Society · 2017Article
- Thieme Chemistry Journals Awardees - Where Are They Now? Improved Fmoc Deprotection Methods for the Synthesis of Thioamide-Containing Peptides and Proteins.Synlett : accounts and rapid communications in synthetic organic chemistry · 2017Article
- The effects of thioamide backbone substitution on protein stability: a study in α-helical, β-sheet, and polyproline II helical contexts.Chemical science · 2017Article
- Perturbation Approach for Computing Infrared Spectra of the Local Mode of Probe Molecules.Journal of chemical theory and computation · 2017Article
- A prevalent intraresidue hydrogen bond stabilizes proteins.Nature chemical biology · 2016Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Thioamides are sterically almost identical to their oxoamide counterparts, but they are weaker hydrogen bond acceptors. Therefore, thioamide amino acids are excellent candidates for perturbing the energetics of backbone-backbone H-bonds in proteins and hence should be useful in elucidating protein folding mechanisms in a site-specific manner. Herein, we validate this approach by applying it to probe the dynamic role of interstrand H-bond formation in the folding kinetics of a well-studied β-hairpin, tryptophan zipper. Our results show that reducing the strength of the peptide's backbone-backbone H-bonds, except the one directly next to the β-turn, does not change the folding rate, suggesting that most native interstrand H-bonds in β-hairpins are formed only after the folding transition state.
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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.