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Literature summary for 2.3.2.2 extracted from

  • Castonguay, R.; Lherbet, C.; Keillor, J.W.
    Kinetic studies of rat kidney gamma-glutamyltranspeptidase deacylation reveal a general base-catalyzed mechanism (2003), Biochemistry, 42, 11504-11513.
    View publication on PubMed
Search for more literature for 2.3.2.2

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
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Source Tissue

Source Tissue Comment Organism Textmining
kidney
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 Rattus norvegicus
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5-L-glutamyl-4-nitroanilide + L-methioninamide
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methioninamide
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5-L-glutamyl-4-nitroanilide + L-methionyl(2,2,2-trifluoroethylamide)
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methionyl(2,2,2-trifluoroethylamide)
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5-L-glutamyl-4-nitroanilide + L-methionyl(2-fluoroethylamide)
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methionyl(2-fluoroethylamide)
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5-L-glutamyl-4-nitroanilide + L-methionyl(3,3,3-trifluoropropylamide)
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methionyl(3,3,3-trifluoropropylamide)
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5-L-glutamyl-4-nitroanilide + L-methionylethylamide
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methionylethylamide
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5-L-glutamyl-4-nitroanilide + L-methionylpropylamide
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 Rattus norvegicus 4-nitroaniline + 5-L-glutamyl-L-methionylpropylamide
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additional information the mechanism of the deacylation step of GGT-mediated transpeptidation using L-methionine derivatives as acceptor substrates is consistent with the observed Bronsted linear free energy relationship, pH-rate profile, and solvent kinetic isotope effects. It is proposed that in the rate-limiting step these acceptor substrates carry out a nucleophilic attack on the acyl-enzyme intermediate, with simultaneous deprotonation of the nucleophilic amino group, to form a tetrahedral intermediate. At the transition state, nucleophilic attack is more advanced than deprotonation of the amine, leading to significant development of positive charge on the nucleophilic nitrogen Rattus norvegicus ?
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