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Issue 32, 2007
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Intramolecular recognition in a jet-cooled short peptide chain: γ-turn helicity probed by a neighbouring residue

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Abstract

γ-Turn, the shortest secondary structure of peptides, exists as two helical forms γL and γD of opposite handedness. The present gas phase study of capped L-Phe-Xxx peptides (Xxx = L-Ala, D-Ala or Aib: aminoisobutyric acid) provides a unique example of intramolecular chiral recognition of the γ-turn helicity on Ala or Aib by the neighbouring residue Phe within the chain. With the chiral L- or D-Ala residues, the presence of a side-chain operates a discrimination between the two helical forms: one of them is widely favoured over the other (γL or γD, respectively). This enables us to validate and calibrate the recognition capabilities of the nearby L-Phe residue. The discriminating interactions have been precisely characterized from their spectroscopic UV and IR signatures and identified by comparison with quantum chemistry calculations. Then, in the case of the non-chiral residue Aib, the two helical forms of the γ-turn, which are simultaneously observed in the jet, have been discriminated and assigned by comparison with the chiral residues. The relative abundances of the diastereomeric forms L-Phe-Aib(γL) and L–Phe-Aib(γD) enable us to determine the most efficient recognition configuration.

Graphical abstract: Intramolecular recognition in a jet-cooled short peptide chain: γ-turn helicity probed by a neighbouring residue

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Publication details

The article was received on 26 Mar 2007, accepted on 17 May 2007 and first published on 20 Jun 2007


Article type: Paper
DOI: 10.1039/B704573E
Citation: Phys. Chem. Chem. Phys., 2007,9, 4491-4497
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    Intramolecular recognition in a jet-cooled short peptide chain: γ-turn helicity probed by a neighbouring residue

    E. Gloaguen, F. Pagliarulo, V. Brenner, W. Chin, F. Piuzzi, B. Tardivel and M. Mons, Phys. Chem. Chem. Phys., 2007, 9, 4491
    DOI: 10.1039/B704573E

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