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.

Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides / E. Botana, S. Ongeri, R. Arienzo, M. Demarcus, J. Frey, U. Piarulli, D. Potenza, J. Kilburn, C.M.A. Gennari. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2001:24(2001), pp. 4625-4634. [10.1002/1099-0690(200112)2001:24<4625::AID-EJOC4625>3.0.CO;2-L]

Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides

D. Potenza;C.M.A. Gennari
Ultimo
2001

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.
enantioselectivity ; host-guest systems ; molecular recognition ; peptides ; receptors
Settore CHIM/06 - Chimica Organica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/175249
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