Induction of unexpected left-handed helicity by an N-terminal L-amino acid in an otherwise achiral peptide chain.

@article{Brown2012InductionOU,
  title={Induction of unexpected left-handed helicity by an N-terminal L-amino acid in an otherwise achiral peptide chain.},
  author={Robert A. Brown and Tommaso Marcelli and Matteo De Poli and Jordi Sol{\`a} and Jonathan Clayden},
  journal={Angewandte Chemie},
  year={2012},
  volume={51 6},
  pages={
          1395-9
        }
}
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References

SHOWING 1-10 OF 54 REFERENCES
Conformational analysis of supramolecular polymerization processes of disc-like molecules
N,N′,N′′-Trialkylbenzene-1,3,5-tricarboxamides (BTAs) cooperatively self-assemble into one-dimensional, helical supramolecular polymers in apolar alkane solutions. Previous studies revealed that the
Absolute control of helical handedness in quinoline oligoamides.
TLDR
The synthesis of quinoline-derived helically folded aromatic oligoamides functionalized by various chiral functions at their N-terminus is reported and a rationale for the efficiency of helix handedness induction based on a combination of steric factors and intramolecular hydrogen bonding is proposed.
Chiral information harvesting in dendritic metallopeptides.
TLDR
The remote control of the dynamic chirality of metal centres, coordinated by 2,2'-bipyridine ligands bearing dynamic helical oligopeptides, is reported, and it is shown that when a mixture of chiral and achiral peptide ligands is used, both the chiralities of the metal centre and that of the a chiral oligopePTide helices are significantly amplified.
Measuring screw-sense preference in a helical oligomer by comparison of 13C NMR signal separation at slow and fast exchange.
TLDR
It is demonstrated, using a set of labeled peptide analogues, that simple analysis of peak separation in their (13)C NMR spectra at slow and fast exchange allows an accurate value for the ratio of helical conformers to be obtained.
Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a 13C label into one of the two enantiotopic methyl
Determination of the X‐ray structure of the snake venom protein omwaprin by total chemical synthesis and racemic protein crystallography
TLDR
Racemic crystallography once again proved to be a valuable method for obtaining crystals of recalcitrant proteins and for determining high‐resolution X‐ray structures by direct methods.
N-versus C-terminal control over the screw-sense preference of the configurationally achiral, conformationally helical peptide motif Aib(8)GlyAib(8).
TLDR
X-ray crystallography indicates that Aib( 8)GlyAib(8) forms the longest 3(10) helical structure observed crystallographically to date.
Total chemical synthesis and X-ray structure of kaliotoxin by racemic protein crystallography.
TLDR
The total synthesis of kaliotoxin by 'one pot' native chemical ligation of three synthetic peptides gave crystals in the centrosymmetric space group P1 that diffracted to atomic-resolution, enabling the X-ray structure of kAliotoxin to be determined by direct methods.
Collagen structure and stability.
TLDR
The fibrillar structure of type I collagen-the prototypical collagen fibril-has been revealed in detail and will guide further development of artificial collagenous materials for biomedicine and nanotechnology.
...
1
2
3
4
5
...