Miltschitzky, Stefan and Michlova, Veronika and Stadlbauer, Stefan and König, Burkhard (2006) Synthesis of substituted pyrimidine hydrazine acids (PHA) and their use in peptide recognition. Heterocycles 67 (1), pp. 135-160.
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Substituted pyrimidine-hydrazine-acids (PHA) were prepared from orotic acid in five synthetic steps and high yields. Their geometry of hydrogen bond acceptor and donor sites make them suitable for the molecular recognition of peptide β-sheets. In non-protic solvents the PHA unit emits at around 420 nm after irradiation at 281 nm. The emission intensity decreases upon peptide binding and signals the binding event. Peptides consisting of PHAs and natural amino acids or a turn structure motif were prepared. The investigation of the intramolecular binding pattern by NMR spectroscopy revealed the expected interaction of the PHA and peptide β-sheet.
|Date:||1 January 2006|
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
|Projects:||GRK 760, Graduiertenkolleg Medizinische Chemie|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||05 Jul 2006|
|Last Modified:||10 Mar 2011 11:42|