Glucosinolate biosynthesis from methionine (WP4597)

Arabidopsis thaliana

This pathway describes the glucosinolate derived from methionine in Arabidopsis thaliana. This is based on the KEGG pathway and PlantCyc. Some pathway entities are unknown and being investigated, these are denoted as "Catalyst" and "Metabolite" for now.

Authors

Mikiko Takahashi , Atsushi Fukushima , Kristina Hanspers , Martina Summer-Kutmon , and Eric Weitz

Activity

last edited

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Organisms

Arabidopsis thaliana

Communities

Annotations

Pathway Ontology

classic metabolic pathway

Participants

Label Type Compact URI Comment
3-(Methylsulfinyl)propyl-glucosinolate Metabolite chebi:5406
3-Hydroxypropyl-glucosinolate Metabolite knapsack:C00007340
Methionine Metabolite knapsack:C00001379
3-Sinapoyloxypropyl-glucosinolate Metabolite pubchem.compound:90657803
2-Benzoyloxy-3-butenyl glucosinolate Metabolite pubchem.compound:90657992
S-(4-Methylthiobutylthiohydroximoyl)-L-cysteine Metabolite kegg.compound:C17242
2-Oxo-4-methylthiobutanoic acid Metabolite hmdb:HMDB0001553
Homomethionine Metabolite kegg.compound:C17213
2-(2'-Methylthio)ethylmalic acid Metabolite kegg.compound:C17210
2-Propenyl glucosinolate Metabolite chebi:79317
3-Methylthiopropyl-desulfoglucosinolate Metabolite kegg.compound:C17244
3-Benzoyloxypropyl-glucosinolate Metabolite knapsack:C00007358
2-Oxo-5-methylthiopentanoic acid Metabolite chebi:50260
3-(2'-Methylthio)ethylmalic acid Metabolite kegg.compound:C17212
4-Methylthiobutanaldoxime Metabolite kegg.compound:C17241
3-Methylthiopropyl glucosinolate Metabolite chebi:79326
4-Methylthiobutylthiohydroximate Metabolite chebi:80984
2-(3'-Methylthio)propylmalic acid Metabolite kegg.compound:C17214
2-Oxo-6-methylthiopentanoic acid Metabolite kegg.compound:C17216
3-(3'-Methylthio)propylmalic acid Metabolite kegg.compound:C17215
Dihomomethionine Metabolite kegg.compound:C17217
5-Methylthiopentanaldoxime Metabolite kegg.compound:C17241
4-Methylthiobutyl-desulfoglucosinolate Metabolite kegg.compound:C17248
4-Methylthiobutyl glucosinolate Metabolite kegg.compound:C08409
3-Butenyl glucosinolate Metabolite knapsack:C00007586
4-Hydroxybutyl-glucosinolate Metabolite knapsack:C00007342
4-(Methylsulfinyl)butyl glucosinolate Metabolite knapsack:C00007545
4-Benzoyloxybutyl glucosinolate Metabolite knapsack:C00007359
2-Hydroxy 3-butenyl glucosinolate Metabolite knapsack:C00001486
4-Sinapoyloxybutyl-glucosinolate Metabolite pubchem.compound:46173533
2-Sinapoyloxy-3-butenyl glucosinolate Metabolite pubchem.compound:90658722
2-(4'-Methylthio)butylmalic acid Metabolite kegg.compound:C17218
2-Oxo-7-methylthioheptanoic acid Metabolite kegg.compound:C17220
3-(4'-Methylthio)butylmalic acid Metabolite kegg.compound:C17219
Trihomomethionine Metabolite kegg.compound:C17221
6-Methylthiohexanaldoxime Metabolite kegg.compound:C17246
5-Methylthiopentyl glucosinolate Metabolite kegg.compound:C08401
2-(5'-Methylthio)pentylmalic acid Metabolite kegg.compound:C17222
2-Oxo-8-methylthiooctanoic acid Metabolite kegg.compound:C17224
3-(5'-Methylthio)pentylmalic acid Metabolite kegg.compound:C17223
Tetrahomomethionine Metabolite kegg.compound:C17225
7-Methylthioheptanaldoxime Metabolite kegg.compound:C17249
6-Methylthiohexyl glucosinolate Metabolite kegg.compound:C17250
2-(7'-Methylthio)heptylmalic acid Metabolite kegg.compound:C17230
2-Oxo-10-methylthiodecanoic acid Metabolite kegg.compound:C17232
3-(7'-Methylthio)heptylmalic acid Metabolite kegg.compound:C17231
2-(6'-Methylthio)hexylmalic acid Metabolite kegg.compound:C17226
2-Oxo-9-methylthiononanoic acid Metabolite kegg.compound:C17228
3-(6'-Methylthio)hexylmalic acid Metabolite kegg.compound:C17227
Pentahomomethionine Metabolite kegg.compound:C17229
8-Methylthiooctanaldoxime Metabolite kegg.compound:C17251
7-Methylthioheptyl glucosinolate Metabolite kegg.compound:C17252
7-Methylthioheptyl-desulfoglucosinolate Metabolite kegg.compound:C21650
Hexahomomethionine Metabolite kegg.compound:C17233
9-Methylthiononanaldoxime Metabolite kegg.compound:C17253
8-Methylthiooctyl glucosinolate Metabolite kegg.compound:C17254
8-Methylthiooctyl-desulfoglucosinolate Metabolite kegg.compound:C21746
5-(Methylsulfinyl)pentyl glucosinolate Metabolite knapsack:C00007345
6-(Methylsulfinyl)hexyl glucosinolate Metabolite knapsack:C00007348
7-(Methylsulfinyl)heptyl glucosinolate Metabolite knapsack:C00007352
8-(Methylsulfinyl)octyl glucosinolate Metabolite knapsack:C00007355
4-Pentenyl glucosinolate Metabolite chebi:79318
9-(Methylsulfinyl)nonyl glucosinolate Metabolite knapsack:C00007832
CYP79F1 GeneProduct tair.locus:AT1G16410.1
MAM1 GeneProduct tair.locus:AT5G23010
BCAT4 GeneProduct tair.locus:AT3G19710
BCAT3 GeneProduct tair.locus:AT3G49680
CYP83A1 GeneProduct tair.locus:AT4G13770
SUR1 GeneProduct tair.locus:AT2G20610
UGT74B1 GeneProduct tair.locus:AT1G24100
IIL1 GeneProduct tair.locus:AT4G13430
IMD1 GeneProduct tair.locus:AT5G14200
BCAT3 GeneProduct tair.locus:AT3G49680
IMD1 GeneProduct tair.locus:AT5G14200
IMS2 GeneProduct tair.locus:AT5G23020
IMD1 GeneProduct tair.locus:AT5G14200
IMS2 GeneProduct tair.locus:AT5G23020
IMD1 GeneProduct tair.locus:AT5G14200
IMS2 GeneProduct tair.locus:AT5G23020
IMD1 GeneProduct tair.locus:AT5G14200
IMS2 GeneProduct tair.locus:AT5G23020
IMS2 GeneProduct tair.locus:AT5G23020
CYP79F2 GeneProduct tair.locus:AT1G16400
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
IIL1 GeneProduct tair.locus:AT4G13430
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
IMD1 GeneProduct tair.locus:AT5G14200
IIL1 GeneProduct tair.locus:AT4G13430
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
IIL1 GeneProduct tair.locus:AT4G13430
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
IIL1 GeneProduct tair.locus:AT4G13430
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
IIL1 GeneProduct tair.locus:AT4G13430
IPMI2 GeneProduct tair.locus:AT2G43100
IPMI1 GeneProduct tair.locus:AT3G58990
CYP79F1 GeneProduct tair.locus:AT1G16410.1
CYP79F1 GeneProduct tair.locus:AT1G16410.1
CYP79F1 GeneProduct tair.locus:AT1G16410.1
CYP79F1 GeneProduct tair.locus:AT1G16410.1
CYP79F1 GeneProduct tair.locus:AT1G16410.1
CYP79F2 GeneProduct tair.locus:AT1G16400
CYP79F2 GeneProduct tair.locus:AT1G16400
SOT18 GeneProduct tair.locus:AT1G74090
SOT17 GeneProduct tair.locus:AT1G18590
SOT16 GeneProduct tair.locus:AT1G74100
SOT18 GeneProduct tair.locus:AT1G74090
SOT17 GeneProduct tair.locus:AT1G18590
SOT16 GeneProduct tair.locus:AT1G74100
SOT18 GeneProduct tair.locus:AT1G74090
SOT17 GeneProduct tair.locus:AT1G18590
SOT18 GeneProduct tair.locus:AT1G74090
SOT17 GeneProduct tair.locus:AT1G18590
MAM1 GeneProduct tair.locus:AT5G23010
IMS2 GeneProduct tair.locus:AT5G23020

References

  1. Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle. Textor S, Bartram S, Kroymann J, Falk KL, Hick A, Pickett JA, et al. Planta. 2004 Apr;218(6):1026–35. PubMed Europe PMC Scholia
  2. Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. Piotrowski M, Schemenewitz A, Lopukhina A, Müller A, Janowitz T, Weiler EW, et al. J Biol Chem. 2004 Dec 3;279(49):50717–25. PubMed Europe PMC Scholia
  3. Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis. Grubb CD, Zipp BJ, Ludwig-Müller J, Masuno MN, Molinski TF, Abel S. Plant J. 2004 Dec;40(6):893–908. PubMed Europe PMC Scholia
  4. The three desulfoglucosinolate sulfotransferase proteins in Arabidopsis have different substrate specificities and are differentially expressed. Klein M, Reichelt M, Gershenzon J, Papenbrock J. FEBS J. 2006 Jan;273(1):122–36. PubMed Europe PMC Scholia
  5. MAM3 catalyzes the formation of all aliphatic glucosinolate chain lengths in Arabidopsis. Textor S, de Kraker JW, Hause B, Gershenzon J, Tokuhisa JG. Plant Physiol. 2007 May;144(1):60–71. PubMed Europe PMC Scholia
  6. Kinetics and substrate specificities of desulfo-glucosinolate sulfotransferases in Arabidopsis thaliana. Klein M, Papenbrock J. Physiol Plant. 2009 Feb;135(2):140–9. PubMed Europe PMC Scholia
  7. Arabidopsis thaliana encodes a bacterial-type heterodimeric isopropylmalate isomerase involved in both Leu biosynthesis and the Met chain elongation pathway of glucosinolate formation. Knill T, Reichelt M, Paetz C, Gershenzon J, Binder S. Plant Mol Biol. 2009 Oct;71(3):227–39. PubMed Europe PMC Scholia
  8. Glucosinolate breakdown in Arabidopsis: mechanism, regulation and biological significance. Wittstock U, Burow M. Arabidopsis Book. 2010;8:e0134. PubMed Europe PMC Scholia