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Literature summary for 2.3.2.2 extracted from

  • Han, L.; Hiratake, J.; Kamiyama, A.; Sakata, K.
    Design, synthesis, and evaluation of gamma-phosphono diester analogues of glutamate as highly potent inhibitors and active site probes of gamma-glutamyl transpeptidase (2007), Biochemistry, 46, 1432-1447.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
2-amino 4-[4-chlorophenyl(methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 610/per mol * s Escherichia coli
2-amino 4-[4-chlorophenyl(methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 5.0/per mol * s Homo sapiens
2-amino 4-[methyl(phenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 120/per mol * s Escherichia coli
2-amino 4-[methyl(phenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 0.4/per mol * s Homo sapiens
2-amino-4-[(4-methoxyphenyl)(methyl)phosphono]-butanoic acid second-order rate constant for enzyme inactivation is 19/per mol * s Escherichia coli
2-amino-4-[(4-methoxyphenyl)(methyl)phosphono]-butanoic acid second-order rate constant for enzyme inactivation is 0.16/per mol * s Homo sapiens
2-amino-4-[1-[N-(carboxymethyl)carbamoyl]propyl(phenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 80/per mol * s Escherichia coli
2-amino-4-[1-[N-(carboxymethyl)carbamoyl]propyl(phenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 75/per mol * s Homo sapiens
2-amino-4-[4-cyanophenyl(methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 12000/per mol * s Escherichia coli
2-amino-4-[4-cyanophenyl(methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 46/per mol * s Homo sapiens
2-amino-4-[methyl(4-methylphenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 24/per mol * s Escherichia coli
2-amino-4-[methyl(4-methylphenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 0.24/per mol * s Homo sapiens
2-amino-4-[methyl(4-methylumbelliferyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 16000/per mol * s Escherichia coli
2-amino-4-[methyl(4-methylumbelliferyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 2400/per mol * s Homo sapiens
2-amino-4-[methyl(4-nitrophenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 35000/per mol * s Escherichia coli
2-amino-4-[methyl(4-nitrophenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 130/per mol * s Homo sapiens
2-amino-4-[methyl(4-trifluoromethylphenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 2900/per mol * s Escherichia coli
2-amino-4-[methyl(4-trifluoromethylphenyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 12/per mol * s Homo sapiens
2-amino-4-[[3-(carboxymethyl)phenyl](methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 150/per mol * s Escherichia coli
2-amino-4-[[3-(carboxymethyl)phenyl](methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 51/per mol * s Homo sapiens
2-amino-4-[[4-(carboxymethyl)phenyl](methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 210/per mol * s Escherichia coli
2-amino-4-[[4-(carboxymethyl)phenyl](methyl)phosphono]butanoic acid second-order rate constant for enzyme inactivation is 0.33/per mol * s Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0126
-
7-(N-gamma-glutamylamino)-4-methylcoumarin 25°C, pH 5.5 Homo sapiens

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Homo sapiens
-
-
-

Reaction

Reaction Comment Organism Reaction ID
a (5-L-glutamyl)-peptide + an amino acid = a peptide + a 5-L-glutamyl amino acid in the human enzyme, a specific residue in the Cys-Gly binding site plays a critical role in recognizing the Cys-Gly moiety or the acceptor molecules by interacting with the C-terminal carboxy group, whereas the Cys side chain and the Cys-Gly amide bond are not recognized significantly Homo sapiens
a (5-L-glutamyl)-peptide + an amino acid = a peptide + a 5-L-glutamyl amino acid the Escherichia coli enzyme is a nonselective enzyme that accommodates substrates without specifically recognizing the C-terminal carboxy group of the Cys-Gly moiety of gamma-glutamyl compounds or the acceptor molecules Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7-(N-gamma-glutamylamino)-4-methylcoumarin + H2O
-
Escherichia coli 7-amino-4-methylcoumarin + ?
-
?
7-(N-gamma-glutamylamino)-4-methylcoumarin + H2O
-
Homo sapiens 7-amino-4-methylcoumarin + ?
-
?

Synonyms

Synonyms Comment Organism
gamma-glutamyl transpeptidase
-
Escherichia coli
gamma-glutamyl transpeptidase
-
Homo sapiens