Synthesis, conformational studies and binding properties of acyclic receptors for N-protected amino acids and dipeptides
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)
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Official URL: http://dx.doi.org/10.1002/1099-0690(200112)2001:24...
Description/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.
| Item Type: | Article |
|---|---|
| ISSN: | 1099-0690 (print) |
| Uncontrolled Keywords: | enantioselectivity, host-guest systems, molecular recognition, peptides, receptors, selective peptide binding, combinatorial libraries, molecular tweezers, sequence, identification, stabilization, recognition, terminus, water, host |
| Related URLs: | http://dx.doi.org/10.1002/1099...3.0.CO;2-L |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 19422 |
| URI: | http://eprints.soton.ac.uk/id/eprint/19422 |
| Deposited On: | 14 Feb 2006 |
| Last Modified: | 01 Apr 2012 01:55 |
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