Stadlbauer, Stefan and Riechers, Alexander and Spaeth, Andreas and Koenig, Burkhard (2008) Utilizing reversible copper(II) peptide coordination in a sequence-selective luminescent receptor. CHEMISTRY-A EUROPEAN JOURNAL, 14 (8). pp. 2536-2541. ISSN 0947-6539,
Full text not available from this repository. (Request a copy)Abstract
Although vast information about the coordination ability of amino acids and peptides to metal ions is available, little use of this has been made in the rational design of selective peptide receptors. We have combined a copper(II) nitrilotriacetato (NTA) complex with an ammonium-ion-sensitive and luminescent benzocrown ether. This compound revealed micromolar affinities and selectivities for glycine- and histidine-containing sequences, which closely resembles those of copper(II) ion peptide binding: the two free coordination sites of the copper(II) NTA complex bind to imidazole and amido nitrogen atoms, replicating the initial coordination steps of non-complexed copper(II) ions. The benzocrown ether recognizes the N-terminal amino moiety intramolecularly, and the significantly increased emission intensity signals the binding event, because only if prior coordination of the peptide has taken place is the intramolecular ammonium ion-benzocrown ether interaction of sufficient strength in water to trigger an emission signal. Intermolecular ammonium ion-benzocrown ether binding is not observed. Isothermal titration calorimetry confirmed the binding constants derived from emission titrations. Thus, as deduced from peptide coordination studies, the combination of a truncated copper(IT) coordination sphere and a luminescent benzocrown ether allows for the more rational design of sequence-selective peptide receptors.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | GLY-GLY-HIS; ARTIFICIAL RECEPTORS; COMPLEX-FORMATION; REDOX POTENTIALS; AQUEOUS-SOLUTION; TAGGED PROTEINS; BINDING; RECOGNITION; IONS; CU2+; chelates; crown compounds; fluorescence spectroscopy; molecular recognition; peptides |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 11 Nov 2020 10:09 |
| Last Modified: | 11 Nov 2020 10:09 |
| URI: | https://pred.uni-regensburg.de/id/eprint/31580 |
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