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Flexible but with a defined turn-influence of the template on the binding properties of two-armed receptors.
Journal article

Flexible but with a defined turn-influence of the template on the binding properties of two-armed receptors.

  • 2003-01-18
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2003
Binding Sites
Combinatorial Chemistry Techniques
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Peptides
Piperazines
Pliability
Protein Binding
Substrate Specificity
English 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.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/205560
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