4-N-hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase.
Analogues of glutamic acid were synthesized and evaluated for their inhibitory activity toward glutamine synthetase (EC 6.3.1.2; GS). The title compound, 4-N-hydroxy-L-2,4-diaminobutyric acid (NH-DABA), showed a potent inhibitory activity against GS from both sheep brain and soybean. The inhibition is competitive with respect to glutamic acid and the Ki values of sheep brain GS and soybean GS for NH-DABA are 0.007 mmol and 0.021 mmol, respectively. The activity of inhibition is comparable to those of L-methionine sulfoximine and 2-amino-4-(hydroxymethyl-phosphinyl)butyric acid (phosphinothricin).
D000613:Aminobutyrates / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D005974:Glutamate-Ammonia Ligase / Q000037:antagonists & inhibitors*; D012756:Sheep; D013329:Structure-Activity Relationship
D000613:Aminobutyrates; C054822:4-N-hydroxy-2,4-diaminobutyric acid; D005974:Glutamate-Ammonia Ligase