Botana, Enrique, Ongeri, Sandrine, Arienzo, Rosa, Demarcus, Mariangela, Frey, Jeremy G., Piarulli, Umberto, Potenza, Donatella, Kilburn, Jeremy D. and Gennari, Cesare (2001) Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides. European Journal of Organic Chemistry, (24), 4625-4634. (doi:10.1002/1099-0690(200112)2001:24<4625::AID-EJOC4625>3.0.CO;2-L).
Abstract
Solid-phase syntheses of novel receptors featuring a 2,6- diamidopyridine "head" group and bearing sulfonamidopeptide sidearms are described, NMR conformational studies show that the 'two-armed" receptors collapse into an intramolecularly folded structure through formation of a hydrogen-bonding network. In order to accommodate the guests, receptors have to unfold, breaking the intramolecular hydrogen bonds. The absolute binding constants of receptors with N-protected amino acids and dipeptides are therefore relatively weak. However, one receptor shows a high selectivity for N-CbZ-D-Ala-D-AlaOH over its enantiomer N-Cbz-L-Ala-L-AlaOH.
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