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| - Oxoanion Binding by Flexible GuanidiniocarbonylPyrrole−Ammonium Bis-Cations in Water
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| - The syntheses of several bis-cations 1−5 with a simple primary ammonium cation attached via flexiblelinkers of varying length to a guanidiniocarbonyl pyrrole oxo anion binding site are reported. In UV-binding studies in aqueous buffer solution these bis-cations showed efficient binding of various N-acetylamino acid carboxylates. However, complex affinity is significantly depending on both the anion and thelength of the linker in the bis-cation. With increasing linker length, complex stability first increases untilan optimum is reached for bis-cation 3 with a C4-linker. Then the complex stability decreases again. Thebest binding substrate in this series is N-acetyl phenyl alanine, most likely due to additional cation−π-interactions between the aromatic ring and the guanidiniocarbonyl pyrrole cation. The formation of thecomplex between bis-cation 3 and N-acetyl phenyl alanine carboxylate was investigated further byfluorescence titrations and NOE studies, as well as molecular mechanics calculations.
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