N-octanoylglycine

Three steps

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by GLYATL2, BAAT, HADHA, ACAA2 and 1 moreperoxisome, mitochondrial matrix

• an N(2)-acyl-L-glutamineReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by GLYATL2, SLC7A5, GLYATL1B, GLYATL1extracellular space, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 8 routes

• 3-methylmalateReach from here →
  1. N-octanoylglycine + 2 L-ascorbate + O2 = N-octanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. N-octanoyl-(2S)-hydroxyglycine = octanamide + glyoxylate
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by PAM, CLYBL

• tricosanoyl-CoAReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by GLYATL2, BAAT, SLC27A2, ACSL4 and 6 moreperoxisome, cytosolOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GLYATL2, GSS, PTGES, MGST3 and 4 more

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by GLYATL2, GSS, GPX1, GPX4

• thromboxane B2Reach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and thromboxane B2 (cytosol to extracellular)

  Catalysed by GLYATL2, GSS, SLCO1B1cytosol, extracellular spaceOne of 2 routes

• an S-substituted glutathioneReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by GLYATL2, GSS, GSTT4, GSTA4 and 21 moreOne of 2 routes

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (13S)-hydroperoxy-(9Z,11E)-octadecadienoate + 2 glutathione = (13S)-hydroxy-(9Z,11E)-octadecadienoate + glutathione disulfide + H2O

  Catalysed by GLYATL2, GSS, GPX1, GSTA1 and 2 more

• taurochenodeoxycholateReach from here →
  1. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (GSH)

  Catalysed by GLYATL2, GSS, SLCO1A2, SLC7A9 and 1 morecytosol, extracellular spaceOne of 3 routes