A luminescent receptor with affinity for N-terminal histidine in peptides in aqueous solution

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3362-3365

  Kruppa, Michael ^a   Mandl, Christian ^a   Miltschitzky, Stefan ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; AMMONIA; ETHERS; LUMINESCENT DEVICES; METHANOL; PH EFFECTS; SYNTHESIS (CHEMICAL);

AMMONIUM ION BINDING; ARTIFICIAL HOST COMPOUNDS; HISTIDINE; IMIDAZOLE MOIETY;

POLYPEPTIDES;

AMMONIA; COPPER; CROWN ETHER; DIGLYCINE; HISTIDINE; METHANOL; PEPTIDE;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; LUMINESCENCE; MOLECULAR INTERACTION; PH;

COPPER; CROWN ETHERS; HISTIDINE; IMINO ACIDS; LUMINESCENT AGENTS; MODELS, MOLECULAR; PEPTIDES; PROTEIN BINDING; SOLUTIONS; WATER;

EID: 14944385307     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043930h     Document Type: Article

References (35)

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29. 4 as the reference compound (Φ = 0.546).
30. 4). The presence of the paramagnetic transition-metal ion may quench the emission of the crown ether. Binding of His-containing peptides restores parts of the emission intensity, presumably by part suppression of the quenching mechanism.
31. Hopgood, D.; Angelici, R. J. J. Am. Chem. Soc. 1968, 90, 2508-2513.
32. At this pH the IDA-metal complex is stable, imidazole is not protonated and coordinates to the metal complex, and the lysine side chain bears an ammonium ion, which can bind to the crown ether.
33. A rapid exchange of bound histidines within the dynamic assembly is expected.
34. Only Tyr and Trp could not be used in this assay. Tyr is not soluble in HEPES buffer, and the indole emission of Trp interferes with the emission of 5. However, calorimetric titration showed no binding of the amino acids to 5.
35. All amino acids bear an ammonium group under the experimental conditions. But in aqueous solution the affinity of the ammonium group to the benzo crown ether is too weak to give any emission response.