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Literature summary extracted from

  • Gallwitz, H.; Bonse, S.; Martinez-Cruz, A.; Schlichting, I.; Schumacher, K.; Krauth-Siegel, R.L.
    Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies (1999), J. Med. Chem., 42, 364-372.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.8.1.12 additional information activity is dependent on a redox-active cysteine at the active centre Trypanosoma cruzi

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.8.1.7 structure analysis overview, ligand binding, active center Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.8.1.7 ajoene i.e. (E,Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide, natural compound from garlic, Allium sativum, covalent inhibition, but also substrate; time- and temperature-dependent inhibition, mixed disulfide between cative site Cys58 and the inhibitor, modified enzyme shows a markedly increased oxidative activity Homo sapiens
1.8.1.12 ajoene i.e. (E,Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide, natural compound from garlic, Allium sativum, covalent inhibition, but also substrate; time- and temperature-dependent inhibition Trypanosoma cruzi

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.8.1.7 0.16
-
 diallyl trisulfide
-
 Homo sapiens
1.8.1.7 0.38
-
 (Z)-ajoene
-
 Homo sapiens
1.8.1.7 0.8
-
 (E)-ajoene
-
 Homo sapiens
1.8.1.12 2
-
 (E,Z)-ajoene above, with NADPH Trypanosoma cruzi

Organism

EC Number Organism UniProt Comment Textmining
1.8.1.7 Homo sapiens
-
-
-
1.8.1.12 Trypanosoma cruzi
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
1.8.1.7 2 glutathione + NADP+ = glutathione disulfide + NADPH + H+ mechanism Homo sapiens
a
1.8.1.12 trypanothione + NADP+ = trypanothione disulfide + NADPH + H+ mechanistic reaction scheme, structure-function relation Trypanosoma cruzi
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.8.1.7 (Z)-ajoene + NADPH + H+
-
 Homo sapiens 4,5,9-trithiadodeca-1,6,11-triene + 4,8,9,13-tetrathiahexadeca-1,6,10,15-tetraene + NADP+
-
 r
1.8.1.7 2 ajoene + 4 NADPH + 4 H+ i.e. (E,Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide, substrate and inhibitor Homo sapiens 4,8,9,13-tetrathiahexadeca-1,6,1,15-tetraene + 4 NADP+ + 2 allylmercaptan
-
 ?
1.8.1.7 2 ajoene + 4 NADPH + 4 H+ also formation of single-electron reduced product and concomitantly superoxide anion radicals Homo sapiens 4,8,9,13-tetrathiahexadeca-1,6,1,15-tetraene + 4 NADP+ + 2 allylmercaptan
-
 ?
1.8.1.7 ajoene + NADPH + H+ i.e. (E,Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide, substrate and inhibitor Homo sapiens 4,5,9-trithiadodeca-1,6,11-triene + NADP+ + H2O
-
 ?
1.8.1.7 ajoene + NADPH + H+ also formation of single-electron reduced product and concomitantly superoxide anion radicals Homo sapiens 4,5,9-trithiadodeca-1,6,11-triene + NADP+ + H2O
-
 ?
1.8.1.7 diallyl trisulfide + NADPH
-
 Homo sapiens ?
-
 ?
1.8.1.7 GSSG + NADPH
-
 Homo sapiens glutathione + NADP+
-
 ir
1.8.1.12 (E,Z)-ajoene + NADPH + H+
-
 Trypanosoma cruzi ?
-
 r
1.8.1.12 ajoene + NADPH i.e. (E,Z)-4,5,9-trithiadodeca-1,6,11-triene-9-oxide, substrate and inhibitor Trypanosoma cruzi ?
-
 ?
1.8.1.12 trypanothione disulfide + NADPH
-
 Trypanosoma cruzi trypanothione + NADP+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.8.1.12 TR
-
 Trypanosoma cruzi

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.8.1.7 0.16
-
 diallyl trisulfide
-
 Homo sapiens
1.8.1.7 0.34
-
 (E)-ajoene
-
 Homo sapiens
1.8.1.7 1.47
-
 (E)-ajoene + GSH Homo sapiens
1.8.1.7 2.6
-
 (Z)-ajoene
-
 Homo sapiens
1.8.1.12 0.67
-
 (E,Z)-ajoene
-
 Trypanosoma cruzi

Cofactor

EC Number Cofactor Comment Organism Structure
1.8.1.7 FAD FAD enzyme Homo sapiens
1.8.1.7 NADPH
-
 Homo sapiens
1.8.1.12 FAD
-
 Trypanosoma cruzi
1.8.1.12 NADPH
-
 Trypanosoma cruzi