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Synthesis and binding properties of guanidinium biscarboxylates

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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 δ-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.

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Acknowledgments

We thank the Deutsche Forschungsgemeinschaft (GRK 640) and the University of Regensburg for support of this work. We thank Dr. R. Vasold and K. Lehner for HPLC analyses.

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  1. Institut für Organische Chemie, Universität Regensburg, 93040, Regensburg, Germany

    Andreas Späth, Janina Gonschor & Burkhard König

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  1. Andreas Späth
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  2. Janina Gonschor
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  3. Burkhard König
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Correspondence to Burkhard König.

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Späth, A., Gonschor, J. & König, B. Synthesis and binding properties of guanidinium biscarboxylates. Monatsh Chem 142, 1289–1308 (2011). https://doi.org/10.1007/s00706-011-0660-x

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