N-tetradecanoyl-(2S)-hydroxyglycine

Three steps

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by PAM, GLYATL2One of 2 routes

• 2-hydroxy-4-methylvaleric acidReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
  3. 4-methyl-2-oxopentanoate reduction

  Catalysed by PAM, AADAT, SDR42E2, AKR1B15 and 16 morecytosol

• heme bReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. Fe(3+)(out) + L-ascorbate(in) = monodehydro-L-ascorbate radical(in) + Fe(2+)(out) + H(+)
  3. Ferrochelatase, Mitochondrial

  Catalysed by PAM, CYB561D2, CYB561, CYBRD1 and 3 moreinner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 3 routes

• N-benzoylglycineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by PAM, GLYATL2mitochondrial matrixOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by PAM, GLYATL2, MECRmitochondrial matrixOne of 5 routes

• N-(tetradecanoyl)-sphinganineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. sphinganine + tetradecanoyl-CoA = N-(tetradecanoyl)-sphinganine + CoA + H(+)

  Catalysed by PAM, GLYATL2, CERS6, CERS5

• 3-oxohexadecasphinganineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. tetradecanoyl-CoA + L-serine + H(+) = 3-oxohexadecasphinganine + CO2 + CoA

  Catalysed by PAM, GLYATL2, SPTLC1, SPTLC3

• (R)-adrenalineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. dopamine + 2 L-ascorbate + O2 = (R)-noradrenaline + 2 monodehydro-L-ascorbate radical + H2O
  3. (R)-noradrenaline + S-adenosyl-L-methionine = (R)-adrenaline + S-adenosyl-L-homocysteine + H(+)

  Catalysed by PAM, DBH, PNMT

• 1-tetradecanoyl-sn-glycerol 3-phosphateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)

  Catalysed by PAM, GLYATL2, GPAT3, GPAT2 and 2 morecytosol

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by PAM, GLYATL2, AGPAT2

• N-tetradecanoylsphing-4-enineReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. tetradecamide + H2O = tetradecanoate + NH4(+)
  3. N-tetradecanoylsphing-4-enine + H2O = sphing-4-enine + tetradecanoate

  Catalysed by PAM, FAAH, ASAH1, ACER2 and 1 more

• (2S)-2-aminobutanoateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. (2S)-2-aminobutanoate + glyoxylate = 2-oxobutanoate + glycine

  Catalysed by PAM, GLYATL2, AGXT2One of 6 routes

• 1-(9Z)-octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + tetradecanoyl-CoA = 1-(9Z)-octadecenoyl-2-tetradecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by PAM, GLYATL2, AGPAT2, GPAT3 and 3 more

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. tetradecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by PAM, GLYATL2, LPCAT1

• 1-tetradecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. 2-(9Z-octadecenoyl)-glycerol + tetradecanoyl-CoA = 1-tetradecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by PAM, GLYATL2, MOGAT2, MOGAT1

• 2-iminobutanoateReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. (2S)-2-aminobutanoate + glyoxylate = 2-oxobutanoate + glycine
  3. 2-iminobutanoate + H2O = 2-oxobutanoate + NH4(+)

  Catalysed by PAM, AGXT2, RIDA

• 14-hydroxytetradecanoateReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. tetradecamide + H2O = tetradecanoate + NH4(+)
  3. alkane 1-monooxygenase (myristic acid)

  Catalysed by PAM, FAAH, CYP4A11, CYP4A22cytosolOne of 2 routes

• 3-phenyllactateReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. Formation of Phenyl-Lactate

  Catalysed by PAM, AADATcytosol

• glycodeoxycholateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. Glycodeoxycholate amidohydrolase

  Catalysed by PAM, GLYATL2cytosolOne of 2 routes

• tetradecanalReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. tetradecamide + H2O = tetradecanoate + NH4(+)
  3. tetradecanal + NAD(+) + H2O = tetradecanoate + NADH + 2 H(+)

  Catalysed by PAM, FAAH, ALDH3A2

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by PAM, GLYATL2, CPT2

• (5Z)-tetradecenoyl-CoAReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. stearoyl-CoA 9-desaturase (myristoyl-CoA)

  Catalysed by PAM, GLYATL2, SCD, SCD5cytosol

• N-eicosanoylglycinateReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by PAM, GLYATL2, BAAT

• N-docosanoylglycineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by PAM, GLYATL2, BAAT

• N-hexacosanoylglycineReach from here →
  1. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O
  2. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by PAM, GLYATL2, BAAT

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate
  2. glyoxylate + L-alanine = glycine + pyruvate
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by PAM, AGXT, AGXT2, PDHA1 and 2 moremitochondrial matrix