Conformational properties of 4-mercaptoproline and related derivatives.

@article{Cadamuro2008ConformationalPO,
  title={Conformational properties of 4-mercaptoproline and related derivatives.},
  author={Sergio Alfredo Cadamuro and Rudolf Reichold and Ulrike Kusebauch and H J Musiol and Christian Renner and Paul Tavan and Luis Moroder},
  journal={Angewandte Chemie},
  year={2008},
  volume={47 11},
  pages={
          2143-6
        }
}
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52 Citations
Methods Citations
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52 Citations

Application of (4R)-aminoproline in peptide engineering: conformational bias and pH-responsiveness revisited
How do we make proline residues pH sensitive?
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A novel computational strategy is used to identify an optimal staple for antiparallel β-strands, and then that staple is incorporated within a β-hairpin peptide, which represents promising starting points for developing inhibitors of cellular protein-protein interactions.
Toward Activatable Collagen Mimics: Combining DEPSI "Switch" Defects and Template-Guided Self-Organization to Control Collagen Mimetic Peptides.
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The results of pH jump experiments and thermal denaturation studies provide new insights into the contributions of structural DEPSI defects to the template-guided self-assembly of the CTH motif.
Influence of Lipidation on the Folding and Stability of Collagen Triple Helices-An Experimental and Theoretical Study.
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Temperature denaturation and kinetic studies with a series of collagen mimetic peptides bearing saturated and unsaturated fatty acids with different lengths revealed that longer and more flexible fatty acid appendages increase the stability and the folding rate of collagen triple helices.
Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines
  • V. Kubyshkin
  • Chemistry, Biology
    Beilstein journal of organic chemistry
  • 2020
Fluorine-containing analogues of proline are valuable tools in engineering and NMR spectroscopic studies of peptides and proteins. Their use relies on the fundamental understanding of the interplay…
N-Terminal speciation for native chemical ligation.
Native chemical ligation (NCL) enables the chemical synthesis of peptides via reactions between N-terminal thiolates and C-terminal thioesters under mild, aqueous conditions at pH 7-8. Here we…
Alkylation of g-Azaproline Creates Conformationally Adaptable Proline Derivatives for pH-Responsive Collagen Triple Helices.
Cγ-substituted proline derivatives are valuable tools for developing functionalized collagen peptides for biological and materials investigations, yet the stereochemistry at Cγ can produce undesired…
Why Proline? Influence of Ring-Size on the Collagen Triple Helix.
TLDR
Computer and nuclear magnetic resonance spectroscopic studies with model compounds and thermal denaturation experiments with collagen peptides showed that the ring-size analogs destabilize the triple helix to a similar extent by either mismatching backbone dihedral angles ϕ and ψ (Pip) or by an unfavorable trans/cis amide bond ratio (Aze).
Which DFT levels of theory are appropriate in predicting the prolyl cis–trans isomerization in solution?
DFTs were assessed for the conformational preferences of the peptides containing Pro and its derivatives in chloroform and water.
Stabilization of the triple helix in collagen mimicking peptides.
  • V. Kubyshkin
  • Biology, Chemistry
    Organic & biomolecular chemistry
  • 2019
TLDR
This review summarizes the existing chemical approaches towards stabilization of this structure including the most recent developments and provides essential information needed to design collagen-based biomaterials of the future.
...
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