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Flexible but with a Defined Turn—Influence of the Template on the Binding Properties of Two‐Armed Receptors
Author(s) -
Wennemers Helma,
Nold Matthias C.,
Conza Matteo M.,
Kulicke Klaus J.,
Neuburger Markus
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390046
Subject(s) - diastereomer , diketopiperazines , chemistry , stereochemistry , rational design , turn (biochemistry) , nuclear magnetic resonance spectroscopy , receptor , binding site , crystal structure , combinatorial chemistry , crystallography , materials science , nanotechnology , biochemistry
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.