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Chiral Recognition of Dipeptides in a Biomembrane Model

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journal contribution
posted on 2004-10-20, 00:00 authored by Cecilia Bombelli, Stefano Borocci, Federica Lupi, Giovanna Mancini, Luisa Mannina, Anna Laura Segre, Stéphane Viel
Chiral recognition of the enantiomeric couples of ditryptophan and diphenylalanine was observed by 1H NMR spectroscopy in micelles formed by sodium N-dodecanoyl-l-prolinate. Ditryptophan showed a selective association with the Z domains of the amidic aggregates, whereas diphenylalanine did not show any selectivity in the association. Partition coefficients between water and aggregates were evaluated by diffusion NMR experiments. Intramolecular distances of ditryptophan isomers associated with chiral aggregates were obtained by ROESY experiments and were used as constraints in molecular mechanics calculations. From these calculations, information on the conformation of the peptides in the chiral aggregates was obtained.