KEGG   PATHWAY: nta00785
Entry
nta00785                    Pathway                                
Name
Lipoic acid metabolism - Nicotiana tabacum (common tobacco)
Class
Metabolism; Metabolism of cofactors and vitamins
Pathway map
nta00785  Lipoic acid metabolism
nta00785

Module
nta_M00307  Pyruvate oxidation, pyruvate => acetyl-CoA [PATH:nta00785]
nta_M00621  Glycine cleavage system [PATH:nta00785]
nta_M00881  Lipoic acid biosynthesis, plants and bacteria, octanoyl-ACP => dihydrolipoyl-E2/H [PATH:nta00785]
nta_M00882  Lipoic acid biosynthesis, eukaryotes, octanoyl-ACP => dihydrolipoyl-H [PATH:nta00785]
Other DBs
GO: 0009106
Organism
Nicotiana tabacum (common tobacco) [GN:nta]
Gene
107822010  plastidial lipoyltransferase 2-like [KO:K03801] [EC:2.3.1.181]
107790027  plastidial lipoyltransferase 2-like [KO:K03801] [EC:2.3.1.181]
107772363  octanoyltransferase-like [KO:K23735] [EC:2.3.1.181]
107831321  octanoyltransferase-like [KO:K23735] [EC:2.3.1.181]
107806151  lipoyl synthase, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
107792991  lipoyl synthase 2, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
107789917  lipoyl synthase, chloroplastic-like [KO:K03644] [EC:2.8.1.8]
107774824  lipoyl synthase 2, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
107809305  lipoyl synthase 2, mitochondrial-like [KO:K03644] [EC:2.8.1.8]
107798233  lipoyl synthase, chloroplastic-like [KO:K03644] [EC:2.8.1.8]
107813704  dihydrolipoyl dehydrogenase, mitochondrial [KO:K00382] [EC:1.8.1.4]
107821052  dihydrolipoyl dehydrogenase, mitochondrial-like [KO:K00382] [EC:1.8.1.4]
107802918  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107794842  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107783795  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107823550  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107782283  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107803150  dihydrolipoyl dehydrogenase, mitochondrial-like [KO:K00382] [EC:1.8.1.4]
107816379  dihydrolipoyl dehydrogenase 2, chloroplastic-like [KO:K00382] [EC:1.8.1.4]
107770390  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
107760137  pyruvate dehydrogenase E1 component subunit alpha, mitochondrial-like [KO:K00161] [EC:1.2.4.1]
107799031  pyruvate dehydrogenase E1 component subunit alpha, mitochondrial [KO:K00161] [EC:1.2.4.1]
107760338  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
107797927  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
107814677  pyruvate dehydrogenase E1 component subunit alpha, mitochondrial-like [KO:K00161] [EC:1.2.4.1]
107825096  pyruvate dehydrogenase E1 component subunit alpha-3, chloroplastic-like [KO:K00161] [EC:1.2.4.1]
107798513  pyruvate dehydrogenase E1 component subunit alpha, mitochondrial-like [KO:K00161] [EC:1.2.4.1]
107795071  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
107830854  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
107763479  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
107797637  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
107831547  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial [KO:K00162] [EC:1.2.4.1]
107820994  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
107797920  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
107818291  pyruvate dehydrogenase E1 component subunit beta-3, chloroplastic-like [KO:K00162] [EC:1.2.4.1]
107815578  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
107803873  pyruvate dehydrogenase E1 component subunit beta-1, mitochondrial-like [KO:K00162] [EC:1.2.4.1]
107813986  dihydrolipoyllysine-residue acetyltransferase component 1 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107764742  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
107817385  dihydrolipoyllysine-residue acetyltransferase component 5 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
107802375  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
107827422  dihydrolipoyllysine-residue acetyltransferase component 2 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107817052  dihydrolipoyllysine-residue acetyltransferase component 1 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107772318  dihydrolipoyllysine-residue acetyltransferase component 2 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107797489  dihydrolipoyllysine-residue acetyltransferase component 5 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
107768212  dihydrolipoyllysine-residue acetyltransferase component 2 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107788125  dihydrolipoyllysine-residue acetyltransferase component 2 of pyruvate dehydrogenase complex, mitochondrial-like [KO:K00627] [EC:2.3.1.12]
107809523  dihydrolipoyllysine-residue acetyltransferase component 4 of pyruvate dehydrogenase complex, chloroplastic-like [KO:K00627] [EC:2.3.1.12]
107772051  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
107813217  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
107760583  2-oxoglutarate dehydrogenase, mitochondrial-like [KO:K00164] [EC:1.2.4.2]
107800735  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
107828007  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
107819849  dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex 1, mitochondrial-like [KO:K00658] [EC:2.3.1.61]
107768963  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107771953  2-oxoisovalerate dehydrogenase subunit alpha 2, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107769784  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107805669  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107793791  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107819511  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107786009  2-oxoisovalerate dehydrogenase subunit alpha 1, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107818320  2-oxoisovalerate dehydrogenase subunit alpha 2, mitochondrial-like [KO:K00166] [EC:1.2.4.4]
107826062  2-oxoisovalerate dehydrogenase subunit beta 1, mitochondrial-like [KO:K00167] [EC:1.2.4.4]
107765383  2-oxoisovalerate dehydrogenase subunit beta 1, mitochondrial-like [KO:K00167] [EC:1.2.4.4]
107799279  2-oxoisovalerate dehydrogenase subunit beta 1, mitochondrial-like [KO:K00167] [EC:1.2.4.4]
107783079  lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial-like [KO:K09699] [EC:2.3.1.168]
107820956  lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial-like [KO:K09699] [EC:2.3.1.168]
107781010  glycine dehydrogenase (decarboxylating), mitochondrial [KO:K00281] [EC:1.4.4.2]
107783010  glycine dehydrogenase (decarboxylating), mitochondrial-like [KO:K00281] [EC:1.4.4.2]
107805971  aminomethyltransferase, mitochondrial [KO:K00605] [EC:2.1.2.10]
107783755  aminomethyltransferase, mitochondrial-like [KO:K00605] [EC:2.1.2.10]
107776144  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
107805221  glycine cleavage system H protein, mitochondrial-like [KO:K02437]
107785161  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
107772739  glycine cleavage system H protein, mitochondrial [KO:K02437]
107820179  glycine cleavage system H protein, mitochondrial [KO:K02437]
107778948  glycine cleavage system H protein, mitochondrial-like [KO:K02437]
107775371  glycine cleavage system H protein 2, mitochondrial-like [KO:K02437]
107830384  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
nta00020  Citrate cycle (TCA cycle)
nta00061  Fatty acid biosynthesis
nta00260  Glycine, serine and threonine metabolism
nta00280  Valine, leucine and isoleucine degradation
nta00310  Lysine degradation
nta00620  Pyruvate metabolism
KO pathway
ko00785   
LinkDB

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