Synthesis of functionalized guanidino amino acids

Suhs, Thomas and Koenig, Burkhard (2006) Synthesis of functionalized guanidino amino acids. CHEMISTRY-A EUROPEAN JOURNAL, 12 (31). pp. 8150-8157. ISSN 0947-6539,

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Abstract

We report the synthesis of guanidino amino acids (GuAA), which are structurally related to Arg and resemble a dipeptide consisting of alpha- and gamma-amino acid with a guanidinium group in the main chain. The compounds are available with different protecting groups in gram amounts and are intended as synthetic building blocks for the construction of synthetic oxoanion or peptide receptors. Tyr, Trp or dansyl-functionalized Lys can be introduced as the alpha-amino acid part, which leads to luminescent GuAAs. The compounds signal carboxylate binding in MeOH, DMSO and buffered water by change of the emission intensity. The property may find use in the construction of chemosensors.

Item Type: Article
Uncontrolled Keywords: MOLECULAR RECOGNITION; BINDING-PROPERTIES; CONVENIENT SYNTHESIS; MITSUNOBU PROTOCOL; HIGHLY EFFICIENT; ENTROPY-DRIVEN; RECEPTORS; ANIONS; WATER; COMPLEXATION;
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: 20 Jan 2021 09:10
Last Modified: 20 Jan 2021 09:10
URI: https://pred.uni-regensburg.de/id/eprint/33864

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