Conformational properties of 4-mercaptoproline and related derivatives.

  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},
  volume={47 11},
Application of (4R)-aminoproline in peptide engineering: conformational bias and pH-responsiveness revisited
How do we make proline residues pH sensitive?
Stapled β-Hairpins Featuring 4-Mercaptoproline.
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.
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.
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.
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
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.


Neue natürliche Aminosäuren
Mit Hilfe moderner Trennungsmethoden sind in den letzten 15 Jahren zahlreiche neue Aminosauren entdeckt worden. Es wird versucht, alle wesentlichen Beitrage und Anderungen zur Kenntnis uber das
Enhancing the Proline Effect: Pseudo-Prolines for Tailoring Cis/Trans Isomerization
Cis−trans isomerization of proline-like oxazolidines and thiazolidines, denoted pseudo-prolines, is investigated spectrophotometrically with a chymotrypsin coupled assay and by 1H NMR. A series of
Retention of the cis proline conformation in tripeptide fragments of bovine pancreatic ribonuclease A containing a non-natural proline analogue, 5,5-dimethylproline
Attention is focused on l-5,5-dimethylproline (dmP) as a substitute to lock l-proline (Pro) in a cis conformation in peptides and proteins, to prevent cis/trans isomerization when a protein with cis
Crystal structures, molecular conformations, infrared spectra, and carbon-13 NMR spectra of methylproline peptides in the solid state
Etude des influences de conformation des groupes methyle dans des derives N-acetyl, N'-methylamide de sept monomethylprolines isomeres. L'etude RX montre deux conformations moleculaires (α R ou P II
Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr
Contracted Gaussian basis sets of triple zeta valence (TZV) quality are presented for Li to Kr. The TZV bases are characterized by typically including a single contraction to describe inner shells
COSMO : a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
Starting from the screening in conductors, an algorithm for the accurate calculation of dielectric screening effects in solvents is presented, which leads to rather simple explicit expressions for