Stereochemistry of the inactivation of 4-aminobutyrate: 2-oxoglutarate aminotransferase and L-glutamate 1-carboxylase by 4-aminohex-5-ynoic acid enantiomers.
Incubation of rat brain or bacterial 4-aminobutyrate aminotransferase (EC 2.6.1.19) with both (S)-(+)- and (R)-(-)-enantiomers of 4- aminohex -5- ynoic acid results in a time-dependent irreversible loss of enzymatic activity. Rat brain glutamate decarboxylase (EC 4.1.1.15) is inactivated by the (S)-(+)-enantiomer while the bacterial glutamate decarboxylase is inactivated by the (R)-(-)-enantiomer. In addition, we demonstrate that (R)-(-)-4- aminohex -5- ynoic acid is a selective and effective inhibitor of rat brain 4-aminobutyrate aminotransferase in vivo.
D000612:4-Aminobutyrate Transaminase / Q000037:antagonists & inhibitors*; D000480:Alkynes; D000614:Aminocaproates / Q000494:pharmacology*; D000818:Animals; D001921:Brain / Q000201:enzymology; D004926:Escherichia coli / Q000201:enzymology; D005968:Glutamate Decarboxylase / Q000037:antagonists & inhibitors*; D051381:Rats; D013237:Stereoisomerism; D013997:Time Factors
D000480:Alkynes; D000614:Aminocaproates; C013785:4-amino-5-hexynoic acid; D000612:4-Aminobutyrate Transaminase; D005968:Glutamate Decarboxylase