gamma-L-glutamyl-L-cysteine

Three steps

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by GSS, ALOX12cytosol, extracellular spaceOne of 2 routes

• an alkyl sulfateReach from here →
  1. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  2. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O
  3. an alcohol + 3'-phosphoadenylyl sulfate = an alkyl sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by GSS, CP, PRDX6, SULT2B1 and 2 more

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by GSS, CYP1A1, CYP1A2, CYP2E1 and 24 morecytosol, extracellular spaceOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by GSS, CYP1A1, CYP1A2, CYP2E1 and 23 morecytosol, extracellular spaceOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by GSS, ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by GSS, ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by GSS, ABHD16Acytosol, extracellular space

• (5Z)-tetradecenoyl-CoAReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by GGCT, GGACT, NAGS, SLC27A2 and 7 morecytosol, mitochondrial matrixOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by GGCT, GGACT, NAGS, ACADM and 3 morecytosol, mitochondrial matrix

• 11beta-prostaglandin F2Reach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of GSH and prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by GSS, SLCO2A1, AKR1C3, AKR1C2cytosol, extracellular space

• N-tetradecanoylglycineReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by GGCT, GGACT, SLC3A2, SLC7A5 and 2 morecytosol, extracellular space

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by GGCT, GGACT, NAGS, HADHA and 2 morecytosol, mitochondrial matrix

• N-eicosanoylglycinateReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by GGCT, GGACT, SLC3A2, SLC7A5 and 2 morecytosol, extracellular space

• N-docosanoylglycineReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by GGCT, GGACT, SLC3A2, SLC7A5 and 2 morecytosol, extracellular space

• N-hexacosanoylglycineReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by GGCT, GGACT, SLC3A2, SLC7A5 and 2 morecytosol, extracellular space

• an N(2)-acyl-L-glutamineReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. transport of cysteine and glutamine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by GGCT, GGACT, SLC3A2, SLC7A5 and 3 morecytosol, extracellular space

• (7Z)-hexadecenoyl-CoAReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by GGCT, GGACT, NAGS, SLC27A2 and 7 morecytosol, mitochondrial matrixOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by GGCT, GGACT, NAGS, SLC27A2 and 7 morecytosol, mitochondrial matrixOne of 4 routes

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by GSS, SLCO2A1, TBXAS1, CYP2S1 and 1 morecytosol, extracellular space

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GSS, CYP4F8cytosol, extracellular space

• prostaglandin H1Reach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of GSH and prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

  Catalysed by GSS, SLCO2A1, PTGES, PTGES3 and 1 morecytosol, extracellular spaceOne of 2 routes

• 19-hydroxyprostaglandin H2Reach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of GSH and prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GSS, SLCO2A1, CYP4F8cytosol, extracellular space

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by GSS, PTGES, MGST3, GPX1 and 4 more

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by GSS, PTGES, MGST3, GPX1 and 4 more

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by GSS, PTGES, MGST3, GPX1 and 4 more

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by GSS, ALOX15Bcytosol, extracellular space

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by GSS, ALOX15Bcytosol, extracellular space

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. gamma-glutamylcyclotransferase (gamma-glutamyl-cysteine)
  2. L-cysteine hydrogen-sulfide-lyase (deaminating
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by GGCT, GGACT, CTH, PDHA1 and 2 morecytosol, mitochondrial matrix