Flexible but with a defined turn-influence of the template on the binding properties of two-armed receptors |
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Authors: | Wennemers Helma Nold Matthias C Conza Matteo M Kulicke Klaus J Neuburger Markus |
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Institution: | Department of Chemistry, University of Basel St. Johanns Ring 19, 4056 Basel, Switzerland. Helma.Wennemers@unibas.ch |
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Abstract: | Combinatorial binding studies revealed that the di(trans-4-aminoproline)diketopiperazine is an ideal template for two-armed receptors with highly selective binding properties towards peptides. It is not only superior to structurally very different diamines but also to the diastereomeric di(cis-4-aminoproline)diketopiperazine. These empiric results are rationalized by the analysis of the conformation of the diastereomeric diketopiperazines in the solid state, by X-ray crystal structure analysis, as well as by NMR studies in solution: to observe highly selective binding, the template needs to be not only conformationally rigid but it must have a specific turn geometry. The combination of combinatorial binding studies, X-ray crystal structure analysis, and NMR spectroscopy gave insight into why the trans,trans-diketopiperazine is a superior template compared to other diamines. Additionally, the results provide a guide for the rational design of two-armed receptors with good binding properties towards peptidic guests. |
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Keywords: | combinatorial chemistry conformation analysis diketopiperazine molecular recognition proline receptors |
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