ArticleAmino acids2011
Quantum mechanical origin of the conformational preferences of 4-thiaproline and its S-oxides.
Article in Amino acids, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 24 citations in OpenAlex.
- 4-Thiaproline accelerates the slow folding phase of proteins containing cis prolines in the native state by two orders of magnitude.Protein science : a publication of the Protein Society · 2024Article
- Consequences of incorporating thiaproline and its oxidized derivatives into collagen triple helices.Protein science : a publication of the Protein Society · 2023Article
- Modified Peptide Inhibitors of the Keap1-Nrf2 Protein-Protein Interaction Incorporating Unnatural Amino Acids.Chembiochem : a European journal of chemical biology · 2018Article
- Evaluating electronic structure methods for accurate calculation ofJournal of computational chemistry · 2017Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- n→π* interactions engender chirality in carbonyl groups.Organic letters · 2014Article
- A key n→π* Interaction in N-acyl homoserine lactones.ACS chemical biology · 2014Article
- Signatures of n→π* interactions in proteins.Protein science : a publication of the Protein Society · 2014Article
- n→π* interactions in poly(lactic acid) suggest a role in protein folding.Chemical communications (Cambridge, England) · 2013Article
- n→π* interactions of amides and thioamides: implications for protein stability.Journal of the American Chemical Society · 2013Article
- Pyramidalization of a carbonyl C atom in (2S)-N-(seleno-acet-yl)proline methyl ester.Acta crystallographica. Section E, Structure reports online · 2013Article
- Intimate interactions with carbonyl groups: dipole-dipole or n→π*?The Journal of organic chemistry · 2013Article
- An n→π* interaction in aspirin: implications for structure and reactivity.The Journal of organic chemistry · 2011Article
- An evaluation of peptide-bond isosteres.Chembiochem : a European journal of chemical biology · 2011Review
- Sulfur- and seleno-containing amino acids.Amino acids · 2011Article
- The aberrance of the 4S diastereomer of 4-hydroxyproline.Journal of the American Chemical Society · 2010Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The saturated ring and secondary amine of proline spawn equilibria between pyrrolidine ring puckers as well as peptide bond isomers. These conformational equilibria can be modulated by alterations to the chemical architecture of proline. For example, C(γ) in the pyrrolidine ring can be replaced with sulfur, which can be oxidized either stereoselectively to yield diastereomeric S-oxides or completely to yield a sulfone. Here, the thiazolidine ring and peptide bond conformations of 4-thiaproline and its S-oxides were analyzed in an Ac-Xaa-OMe system using NMR spectroscopy, X-ray crystallography, and hybrid density functional theory. The results indicate that the ring pucker of the S-oxides is governed by the gauche effect, and the prolyl peptide bond conformation is determined by the strength of the n → π* interaction between the amide oxygen and the ester carbonyl group. These findings, which are consistent with those of isologous 4-hydroxyprolines and 4-fluoroprolines, substantiate the importance of electron delocalization in amino acid conformation.
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