2-Aminopropane-1,2,3-tricarboxylic acid: Synthesis and co-crystallization with the class A beta-lactamase BS3 of Bacillus licheniformis.

Beck, Joséphine;Sauvage, Eric;Charlier, Paulette;Marchand-Brynaert, Jacqueline
(2008) Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 18, n° 13, p. 3764-3768 (2008)

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Authors
  • Beck, JoséphineUCLouvain
    Author
  • Sauvage, EricUliège
    Author
  • Charlier, PauletteUliège
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
Abstract
The title compound 4 has been prepared in four steps from ethylglycinate in 63% overall yield. This amino analog of citric acid has been co-crystallized with the class A beta-lactamase BS3 of Bacillus licheniformis and the structure of the complex fully analyzed by X-ray diffraction. Tris-ethyl aminocitrate 3 and the free tris-acid 4 have been tested against a member beta-lactamase from all distinct subgroups. They are novel inhibitors of class A beta-lactamases, still modest but more potent than citrate and isocitrate.
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Beck, J., Sauvage, E., Charlier, P., & Marchand-Brynaert, J. (2008). 2-Aminopropane-1,2,3-tricarboxylic acid: Synthesis and co-crystallization with the class A beta-lactamase BS3 of Bacillus licheniformis. Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology, 18(13), 3764-3768. https://doi.org/10.1016/j.bmcl.2008.05.045 (Original work published 2008)