KEGG   PATHWAY: psom00785
Entry
psom00785                   Pathway                                
Name
Lipoic acid metabolism - Papaver somniferum (opium poppy)
Class
Metabolism; Metabolism of cofactors and vitamins
Pathway map
psom00785  Lipoic acid metabolism
psom00785

Module
psom_M00307  Pyruvate oxidation, pyruvate => acetyl-CoA [PATH:psom00785]
psom_M00621  Glycine cleavage system [PATH:psom00785]
psom_M00881  Lipoic acid biosynthesis, plants and bacteria, octanoyl-ACP => dihydrolipoyl-E2/H [PATH:psom00785]
psom_M00882  Lipoic acid biosynthesis, eukaryotes, octanoyl-ACP => dihydrolipoyl-H [PATH:psom00785]
Other DBs
GO: 0009106
Organism
Papaver somniferum (opium poppy) [GN:psom]
Gene
113330550  octanoyltransferase LIP2p, chloroplastic-like [KO:K03801] [EC:2.3.1.181]
113288885  octanoyltransferase LIP2p, chloroplastic-like isoform X1 [KO:K03801] [EC:2.3.1.181]
113359888  octanoyltransferase LIP2p, chloroplastic-like [KO:K03801] [EC:2.3.1.181]
113359527  octanoyltransferase LIP2p, chloroplastic-like [KO:K03801] [EC:2.3.1.181]
113284386  octanoyltransferase LIP2, mitochondrial-like [KO:K23735] [EC:2.3.1.181]
113355541  octanoyltransferase LIP2, mitochondrial-like isoform X1 [KO:K23735] [EC:2.3.1.181]
113310224  octanoyltransferase LIP2, mitochondrial-like [KO:K23735] [EC:2.3.1.181]
113301815  lipoyl synthase 1, chloroplastic-like [KO:K03644] [EC:2.8.1.8]
113306002  lipoyl synthase, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
113297614  lipoyl synthase 1, chloroplastic-like [KO:K03644] [EC:2.8.1.8]
113287638  lipoyl synthase, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
113347002  dihydrolipoyl dehydrogenase, mitochondrial [KO:K00382] [EC:1.8.1.4]
113333129  dihydrolipoyl dehydrogenase, mitochondrial-like [KO:K00382] [EC:1.8.1.4]
113334818  dihydrolipoyl dehydrogenase 2, chloroplastic-like isoform X1 [KO:K00382] [EC:1.8.1.4]
113358155  dihydrolipoyl dehydrogenase 2, chloroplastic-like isoform X1 [KO:K00382] [EC:1.8.1.4]
113289096  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
113343687  pyruvate dehydrogenase E1 component subunit alpha-1, mitochondrial-like [KO:K00161] [EC:1.2.4.1]
113276347  pyruvate dehydrogenase E1 component subunit alpha-1, mitochondrial-like [KO:K00161] [EC:1.2.4.1]
113283144  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
113296906  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
113292177  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
113295441  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
113281399  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
113271555  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like isoform X1 [KO:K00162] [EC:1.2.4.1]
113324436  pyruvate dehydrogenase E1 component subunit beta-2, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
113281126  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial [KO:K00162] [EC:1.2.4.1]
113284368  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
113287340  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
113362816  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
113298760  dihydrolipoyllysine-residue acetyltransferase component 1 of pyruvate dehydrogenase complex, mitochondrial-like isoform X1 [KO:K00627] [EC:2.3.1.12]
113294793  dihydrolipoyllysine-residue acetyltransferase component 3 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
113288368  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
113284373  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
113309804  dihydrolipoyllysine-residue acetyltransferase component 1 of pyruvate dehydrogenase complex, mitochondrial-like isoform X1 [KO:K00627] [EC:2.3.1.12]
113306772  dihydrolipoyllysine-residue acetyltransferase component 5 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
113317963  dihydrolipoyllysine-residue acetyltransferase component 3 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
113298402  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
113358454  dihydrolipoyllysine-residue acetyltransferase component 2 of pyruvate dehydrogenase complex, mitochondrial-like isoform X1 [KO:K00627] [EC:2.3.1.12]
113356142  dihydrolipoyllysine-residue acetyltransferase component 5 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
113322874  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
113343563  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
113310801  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
113313167  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
113303802  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
113333314  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
113287983  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like isoform X1 [KO:K00658] [EC:2.3.1.61]
113347365  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 2, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
113346470  2-oxoisovalerate dehydrogenase subunit alpha 2, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
113356458  2-oxoisovalerate dehydrogenase subunit alpha 2, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
113343772  2-oxoisovalerate dehydrogenase subunit beta 1, mitochondrial-like [KO:K00167] [EC:1.2.4.4]
113274196  2-oxoisovalerate dehydrogenase subunit beta 1, mitochondrial-like [KO:K00167] [EC:1.2.4.4]
113314980  lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial-like [KO:K09699] [EC:2.3.1.168]
113348889  lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial-like [KO:K09699] [EC:2.3.1.168]
113347879  glycine dehydrogenase (decarboxylating), mitochondrial-like [KO:K00281] [EC:1.4.4.2]
113349499  glycine dehydrogenase (decarboxylating), mitochondrial [KO:K00281] [EC:1.4.4.2]
113303865  aminomethyltransferase, mitochondrial-like [KO:K00605] [EC:2.1.2.10]
113287980  aminomethyltransferase, mitochondrial [KO:K00605] [EC:2.1.2.10]
113322311  glycine cleavage system H protein, mitochondrial-like [KO:K02437]
113288335  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
113345808  glycine cleavage system H protein, mitochondrial-like [KO:K02437]
113290122  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
113312771  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
113279389  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
Compound
C00011  CO2
C00014  Ammonia
C00022  Pyruvate
C00024  Acetyl-CoA
C00026  2-Oxoglutarate
C00037  Glycine
C00068  Thiamin diphosphate
C00091  Succinyl-CoA
C00101  Tetrahydrofolate
C00141  3-Methyl-2-oxobutanoic acid
C00143  5,10-Methylenetetrahydrofolate
C00233  4-Methyl-2-oxopentanoate
C00322  2-Oxoadipate
C00527  Glutaryl-CoA
C00630  2-Methylpropanoyl-CoA
C00671  (S)-3-Methyl-2-oxopentanoic acid
C01242  [Protein]-S8-aminomethyldihydrolipoyllysine
C01944  Octanoyl-CoA
C02051  Lipoylprotein
C02147  Dihydrolipoate
C02939  3-Methylbutanoyl-CoA
C02972  Dihydrolipoylprotein
C05125  2-(alpha-Hydroxyethyl)thiamine diphosphate
C05381  3-Carboxy-1-hydroxypropyl-ThPP
C05752  Octanoyl-[acp]
C06157  [Dihydrolipoyllysine-residue succinyltransferase] S-glutaryldihydrolipoyllysine
C06423  Octanoic acid
C15972  Enzyme N6-(lipoyl)lysine
C15973  Enzyme N6-(dihydrolipoyl)lysine
C15974  3-Methyl-1-hydroxybutyl-ThPP
C15975  [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine
C15976  2-Methyl-1-hydroxypropyl-ThPP
C15977  [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine
C15978  2-Methyl-1-hydroxybutyl-ThPP
C15979  [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylbutanoyl)dihydrolipoyllysine
C15980  (S)-2-Methylbutanoyl-CoA
C16238  Lipoyl-AMP
C16241  (R)-Lipoate
C16254  [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine
C16255  [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine
C22159  [Glycine cleavage system H]-N6-octanoyl-L-lysine
C22160  [Lipoyl-carrier protein E2]-N6-octanoyl-L-lysine
C22161  Dihydrolipoyl-AMP
C22667  4-Carboxy-1-hydroxybutyryl-ThPP
Reference
  Authors
Gunther S, McMillan PJ, Wallace LJ, Muller S.
  Title
Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways.
  Journal
Biochem Soc Trans 33:977-80 (2005)
DOI:10.1042/BST20050977
Reference
  Authors
Fujiwara K, Takeuchi S, Okamura-Ikeda K, Motokawa Y.
  Title
Purification, characterization, and cDNA cloning of lipoate-activating enzyme from bovine liver.
  Journal
J Biol Chem 276:28819-23 (2001)
DOI:10.1074/jbc.M101748200
Reference
PMID:9808738
  Authors
Yasuno R, Wada H.
  Title
Biosynthesis of lipoic acid in Arabidopsis: cloning and characterization of the cDNA for lipoic acid synthase.
  Journal
Plant Physiol 118:935-43 (1998)
DOI:10.1104/pp.118.3.935
Reference
  Authors
Gueguen V, Macherel D, Jaquinod M, Douce R, Bourguignon J.
  Title
Fatty acid and lipoic acid biosynthesis in higher plant mitochondria.
  Journal
J Biol Chem 275:5016-25 (2000)
DOI:10.1074/jbc.275.7.5016
Reference
  Authors
Wada M, Yasuno R, Jordan SW, Cronan JE Jr, Wada H.
  Title
Lipoic acid metabolism in Arabidopsis thaliana: cloning and characterization of a cDNA encoding lipoyltransferase.
  Journal
Plant Cell Physiol 42:650-6 (2001)
DOI:10.1093/pcp/pce081
Reference
PMID:8206909
  Authors
Morris TW, Reed KE, Cronan JE Jr.
  Title
Identification of the gene encoding lipoate-protein ligase A of Escherichia coli. Molecular cloning and characterization of the lplA gene and gene product.
  Journal
J Biol Chem 269:16091-100 (1994)
Reference
  Authors
Zhao X, Miller JR, Jiang Y, Marletta MA, Cronan JE.
  Title
Assembly of the covalent linkage between lipoic acid and its cognate enzymes.
  Journal
Chem Biol 10:1293-302 (2003)
DOI:10.1016/j.chembiol.2003.11.016
Reference
  Authors
Nesbitt NM, Baleanu-Gogonea C, Cicchillo RM, Goodson K, Iwig DF, Broadwater JA, Haas JA, Fox BG, Booker SJ.
  Title
Expression, purification, and physical characterization of Escherichia coli lipoyl(octanoyl)transferase.
  Journal
Protein Expr Purif 39:269-82 (2005)
DOI:10.1016/j.pep.2004.10.021
Reference
  Authors
Solmonson A, DeBerardinis RJ
  Title
Lipoic acid metabolism and mitochondrial redox regulation.
  Journal
J Biol Chem 293:7522-7530 (2018)
DOI:10.1074/jbc.TM117.000259
Reference
  Authors
Cronan JE
  Title
Assembly of Lipoic Acid on Its Cognate Enzymes: an Extraordinary and Essential Biosynthetic Pathway.
  Journal
Microbiol Mol Biol Rev 80:429-50 (2016)
DOI:10.1128/MMBR.00073-15
Reference
  Authors
Mayr JA, Feichtinger RG, Tort F, Ribes A, Sperl W
  Title
Lipoic acid biosynthesis defects.
  Journal
J Inherit Metab Dis 37:553-63 (2014)
DOI:10.1007/s10545-014-9705-8
Reference
  Authors
Cao X, Zhu L, Song X, Hu Z, Cronan JE
  Title
Protein moonlighting elucidates the essential human pathway catalyzing lipoic acid assembly on its cognate enzymes.
  Journal
Proc Natl Acad Sci U S A 115:E7063-E7072 (2018)
DOI:10.1073/pnas.1805862115
Reference
  Authors
Soreze Y, Boutron A, Habarou F, Barnerias C, Nonnenmacher L, Delpech H, Mamoune A, Chretien D, Hubert L, Bole-Feysot C, Nitschke P, Correia I, Sardet C, Boddaert N, Hamel Y, Delahodde A, Ottolenghi C, de Lonlay P
  Title
Mutations in human lipoyltransferase gene LIPT1 cause a Leigh disease with secondary deficiency for pyruvate and alpha-ketoglutarate dehydrogenase.
  Journal
Orphanet J Rare Dis 8:192 (2013)
DOI:10.1186/1750-1172-8-192
Reference
  Authors
Habarou F, Hamel Y, Haack TB, Feichtinger RG, Lebigot E, Marquardt I, Busiah K, Laroche C, Madrange M, Grisel C, Pontoizeau C, Eisermann M, Boutron A, Chretien D, Chadefaux-Vekemans B, Barouki R, Bole-Feysot C, Nitschke P, Goudin N, Boddaert N, Nemazanyy I, Delahodde A, Kolker S, Rodenburg RJ, Korenke GC, Meitinger T, Strom TM, Prokisch H, Rotig A, Ottolenghi C, Mayr JA, de Lonlay P
  Title
Biallelic Mutations in LIPT2 Cause a Mitochondrial Lipoylation Defect Associated with Severe Neonatal Encephalopathy.
  Journal
Am J Hum Genet 101:283-290 (2017)
DOI:10.1016/j.ajhg.2017.07.001
Reference
  Authors
Spalding MD, Prigge ST
  Title
Lipoic acid metabolism in microbial pathogens.
  Journal
Microbiol Mol Biol Rev 74:200-28 (2010)
DOI:10.1128/MMBR.00008-10
Reference
  Authors
Guerra AJ, Afanador GA, Prigge ST
  Title
Crystal structure of lipoate-bound lipoate ligase 1, LipL1, from Plasmodium falciparum.
  Journal
Proteins 85:1777-1783 (2017)
DOI:10.1002/prot.25324
Reference
  Authors
Afanador GA, Matthews KA, Bartee D, Gisselberg JE, Walters MS, Freel Meyers CL, Prigge ST
  Title
Redox-dependent lipoylation of mitochondrial proteins in Plasmodium falciparum.
  Journal
Mol Microbiol 94:156-71 (2014)
DOI:10.1111/mmi.12753
Reference
  Authors
Afanador GA, Guerra AJ, Swift RP, Rodriguez RE, Bartee D, Matthews KA, Schon A, Freire E, Freel Meyers CL, Prigge ST
  Title
A novel lipoate attachment enzyme is shared by Plasmodium and Chlamydia species.
  Journal
Mol Microbiol 106:439-451 (2017)
DOI:10.1111/mmi.13776
Reference
  Authors
Storm J, Muller S
  Title
Lipoic acid metabolism of Plasmodium--a suitable drug target.
  Journal
Curr Pharm Des 18:3480-9 (2012)
DOI:10.2174/138161212801327266
Reference
  Authors
Gunther S, Wallace L, Patzewitz EM, McMillan PJ, Storm J, Wrenger C, Bissett R, Smith TK, Muller S
  Title
Apicoplast lipoic acid protein ligase B is not essential for Plasmodium falciparum.
  Journal
PLoS Pathog 3:e189 (2007)
DOI:10.1371/journal.ppat.0030189
Reference
  Authors
Wrenger C, Muller S
  Title
The human malaria parasite Plasmodium falciparum has distinct organelle-specific lipoylation pathways.
  Journal
Mol Microbiol 53:103-13 (2004)
DOI:10.1111/j.1365-2958.2004.04112.x
Reference
  Authors
Martin N, Christensen QH, Mansilla MC, Cronan JE, de Mendoza D
  Title
A novel two-gene requirement for the octanoyltransfer reaction of Bacillus subtilis lipoic acid biosynthesis.
  Journal
Mol Microbiol 80:335-49 (2011)
DOI:10.1111/j.1365-2958.2011.07597.x
Reference
  Authors
Christensen QH, Martin N, Mansilla MC, de Mendoza D, Cronan JE
  Title
A novel amidotransferase required for lipoic acid cofactor assembly in Bacillus subtilis.
  Journal
Mol Microbiol 80:350-63 (2011)
DOI:10.1111/j.1365-2958.2011.07598.x
Related
pathway
psom00020  Citrate cycle (TCA cycle)
psom00061  Fatty acid biosynthesis
psom00260  Glycine, serine and threonine metabolism
psom00280  Valine, leucine and isoleucine degradation
psom00310  Lysine degradation
psom00620  Pyruvate metabolism
KO pathway
ko00785   
LinkDB

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