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

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Beck J, Sauvage E, Charlier P, Marchand-Brynaert J

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

Bioorg Med Chem Lett. 2008 Jul 1;18(13):3764-8. doi: 10.1016/j.bmcl.2008.05.045. Epub 2008 May 16.

PubMed ID

18515103 [ View in PubMed

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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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Drug Targets

Drug	Target	Kind	Organism	Pharmacological Action	Actions
Citric acid	Beta-lactamase	Protein	Bacillus licheniformis	Yes	Weak inhibitor	Details