ArticleBioorganic & medicinal chemistry letters2009
Origin of the stability conferred upon collagen by fluorination.
Article in Bioorganic & medicinal chemistry letters, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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.
The trial behind it
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
26 citing papers in PubMed, 63 citations in OpenAlex.
- Functions of prolyl hydroxylation in elastin.The Journal of biological chemistry · 2026Article
- Around the collagen triple helix: an introduction to studying associated genetic and acquired diseases.Matrix biology : journal of the International Society for Matrix Biology · 2025Review
- Site-Specific Incorporation of Fluorinated Prolines into Proteins and Their Impact on Neighbouring Residues.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- An outcome-defining role for the triple-helical domain in regulating collagen-I assembly.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Peptidic "Molecular Beacon" for Collagen.Biomacromolecules · 2024Article
- Synthesis and Evaluation ofMolecules (Basel, Switzerland) · 2023Article
- HPMA copolymer-collagen hybridizing peptide conjugates targeted to breast tumor extracellular matrix.Journal of controlled release : official journal of the Controlled Release Society · 2023Article
- Impact of bPNA Backbone Structural Constraints and Composition on Triplex Hybridization with DNA.Chembiochem : a European journal of chemical biology · 2022Article
- 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
- Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement.Beilstein journal of organic chemistry · 2021Review
- Conformational landscape of substituted prolines.Biophysical reviews · 2020Review
- Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines.Beilstein journal of organic chemistry · 2020Article
- 4-Fluoroprolines: Conformational Analysis and Effects on the Stability and Folding of Peptides and Proteins.Topics in heterocyclic chemistry · 2017Article
- 4-ketoproline: An electrophilic proline analog for bioconjugation.Biopolymers · 2015Article
- An insight into the biophysical characterization of insoluble collagen aggregates: implication for arthritis.Journal of fluorescence · 2014Article
- Both the cis-trans equilibrium and isomerization dynamics of a single proline amide modulate β2-microglobulin amyloid assembly.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
- Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.Journal of the American Chemical Society · 2013Article
- Peptides that anneal to natural collagen in vitro and ex vivo.Organic & biomolecular chemistry · 2012Article
- Synthesis of 5-fluoro- and 5-hydroxymethanoprolines via lithiation of N-BOC-methanopyrrolidines. Constrained Cγ-exo and Cγ-endo Flp and Hyp conformer mimics.The Journal of organic chemistry · 2012Article
- Interstrand dipole-dipole interactions can stabilize the collagen triple helix.The Journal of biological chemistry · 2011Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
According to a prevailing theory, (2S,4R)-4-hydroxyproline (Hyp) residues stabilize the collagen triple helix via a stereoelectronic effect that preorganizes appropriate backbone torsion angles for triple-helix formation. This theory is consistent with the marked stability that results from replacing the hydroxyl group with the more electron-withdrawing fluoro group, as in (2S,4R)-4-fluoroproline (Flp). Nonetheless, the hyperstability of triple helices containing Flp has been attributed by others to the hydrophobic effect rather than a stereoelectronic effect. We tested this hypothesis by replacing Hyp with 4,4-difluoroproline (Dfp) in collagen-related peptides. Dfp retains the hydrophobicity of Flp, but lacks the ability of Flp to preorganize backbone torsion angles. Unlike Flp, Dfp does not endow triple helices with elevated stability, indicating that the hyperstability conferred by Flp is not due to the hydrophobic effect.
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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.