ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
The Distinct Conformational Landscapes of 4S-Substituted Prolines That Promote an endo Ring Pucker.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 26 citations in OpenAlex.
- Peptidic Catalysts Conformationally Tuned for Fluoride Binding and Delivery.Journal of the American Chemical Society · 2026Article
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- Pauli Exclusion by n→π* Interactions: Implications for Paleobiology.ACS central science · 2024Article
- Progress in the Stereoselective Synthesis Methods of Pyrrolidine-Containing Drugs and Their Precursors.International journal of molecular sciences · 2024Review
- 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
- Natural and Synthetic Halogenated Amino Acids-Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics.Molecules (Basel, Switzerland) · 2021Review
- Protein Design with Fluoroprolines: 4,4-Difluoroproline Does Not Eliminate the Rate-Limiting Step of Thioredoxin Folding.Chembiochem : a European journal of chemical biology · 2021Article
- Stapled β-Hairpins Featuring 4-Mercaptoproline.Journal of the American Chemical Society · 2021Article
- Conformational landscape of substituted prolines.Biophysical reviews · 2020Review
- Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines.Beilstein journal of organic chemistry · 2020Article
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6 authors at 1 institution in 1 country.
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Abstract
4-Substitution on proline directly impacts protein main chain conformational preferences. The structural effects of N-acyl substitution and of 4-substitution were examined by NMR spectroscopy and X-ray crystallography on minimal molecules with a proline 4S-nitrobenzoate. The effects of N-acyl substitution on conformation were attenuated in the 4S-nitrobenzoate context, due to the minimal role of the n→π* interaction in stabilizing extended conformations. By X-ray crystallography, an extended conformation was observed for most molecules. The formyl derivative adopted a δ conformation that is observed at the i+2 position of β-turns. Computational analysis indicated that the structures observed crystallographically represent the inherent conformational preferences of 4S-substituted prolines with electron-withdrawing 4-position substituents. The divergent conformational preferences of 4R- and 4S-substituted prolines suggest their wider structure-specific application in molecular design. In particular, the proline endo ring pucker favored by 4S-substituted prolines uniquely promotes the δ conformation [(ϕ, ψ) ≈(-80°, 0°)] found in β-turns. In contrast to other acyl capping groups, the pivaloyl group strongly promoted trans amide bond and polyproline II helix conformation, with a close n→π* interaction in the crystalline state, despite the endo ring pucker, suggesting its special capabilities in promoting compact conformations in ϕ due to its strongly electron-donating character.
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