Solvent-Dependent Conformational Behaviour of Model Tetrapeptides Containing a Bicyclic Proline Mimetic
Articolo
Data di Pubblicazione:
2004
Citazione:
Solvent-Dependent Conformational Behaviour of Model Tetrapeptides Containing a Bicyclic Proline Mimetic / A. Trabocchi, D. Potenza, A. Guarna. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :22(2004), pp. 4621-4627. [10.1002/ejoc.200400359]
Abstract:
Two model tetrapeptides containing bicyclic analogues of
either D- or L-proline were synthesised and their conformational
properties were studied by NMR in different solvent
systems and by molecular modelling techniques. Compound
1, with the bicyclic D-proline mimetic in the i+1 position, generated
a unique trans isomer, and the peptide showed a well
organised structure, in accordance with the tendency of Dproline
to act as a good turn inducer with respect to its enantiomer.
Peptide 2 displayed structures equilibrating from
type I,II to type VI β-turns, thus confirming the hypothesised relationship between the chirality of BGS/Bgs and proline
enantiomers on nucleating compact turns. Moreover, such
behaviour suggested a tool for peptidomimetic design of reverse
turn peptides containing BGS/Bgs bicyclic proline mimetics,
as the choice of chirality might influence the generation
either of compact γ- and β-turns or of flexible equilibrating
reverse turn structures. The effect of solvent on conformational
behaviour was also studied.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Conformational analysis; NMR spectroscopy; Peptidomimetics; Proline; Reverse turn
Elenco autori:
A. Trabocchi, D. Potenza, A. Guarna
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