Synthesis and binding properties of guanidinium biscarboxylates

Spaeth, Andreas and Gonschor, Janina and Koenig, Burkhard (2011) Synthesis and binding properties of guanidinium biscarboxylates. MONATSHEFTE FUR CHEMIE, 142 (12). pp. 1289-1308. ISSN 0026-9247, 1434-4475

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Abstract

The ammonium ion binding site of the enzyme glutaminase HisF inspired us to design guanidinium biscarboxylates as potential self-organized ionophores in molecular recognition. The syntheses of the title compounds based on aliphatic and aromatic building blocks, along with a general method for the preparation of delta-aminoethoxyacetic acids, are presented in this work. Investigation of the binding properties of the title compounds in dimethyl sulfoxide (DMSO) and methanol solution revealed no ammonium ion affinity, but interaction of the guanidinium moiety with acetate ions.

Item Type: Article
Uncontrolled Keywords: AMINO-ACID RECOGNITION; ION-SELECTIVE LIGANDS; MOLECULAR RECOGNITION; COPPER(II) COMPLEXES; AQUEOUS SOLVENTS; ETHOXYCARBONYL ISOTHIOCYANATE; ELECTROCHEMICAL SENSORS; ADRENALINE RECEPTORS; CARBOXYLATE BINDING; CHIRAL RECOGNITION; Guanidinium; Unnatural amino acid; Recognition; Ligand; Pyrrole
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 26 May 2020 14:22
Last Modified: 26 May 2020 14:22
URI: https://pred.uni-regensburg.de/id/eprint/19764

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