If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
|Superclasses:||Biosynthesis → Secondary Metabolites Biosynthesis → Nitrogen-Containing Secondary Compounds Biosynthesis → Nitrogen-Containing Glucosides Biosynthesis → Glucosinolates Biosynthesis|
Some taxa known to possess this pathway include : Arabidopsis thaliana col
Expected Taxonomic Range: Brassicales
Glucosinolates are nitrogen and sulfur containing secondary metabolites found mainly in the order Capparales, which includes crop plants such as oilseed rape, and the model plant Arabidopsis of the Brassicaceae family. Glucosinolates play an important role in plant defense. They also give the typical sharp taste and odor to many members of the Brassicaceae family such as mustard.
Glucosinolates are derived from amino acids including methionine, phenylalanine and tyrosine, or tryptophan and are grouped into aliphatic, aromatic, and indolic glucosinolates, respectively. Most of our knowledge on glucosinolate metabolism came from studies in Arabidopsis. Arabidopsis accumulates over 30 different glucosinolates, of which the majority are aliphatic glucosinolates derived from chain elongated methionine (range from homomethionine to hexahomomethionine) (compare aliphatic glucosinolate biosynthesis, side chain elongation cycle). The profile of these glucosinolates varies a lot among Arabidopsis ecotypes, a result of allelic variation of the genes involved in glucosinolate biosynthesis.
The conversion of aldoxime to thiohydroximate in glucosinolate biosynthesis involves the incorporation of reduced sulfur. Cysteine was previously suggested to be the sulfur-donor. Recent evidence indicates, however, glutathione is more likely to be the sulfur-donating molecule [GeuFlores09].
GeuFlores09: Geu-Flores F, Nielsen MT, Nafisi M, Moldrup ME, Olsen CE, Motawia MS, Halkier BA (2009). "Glucosinolate engineering identifies a gamma-glutamyl peptidase." Nat Chem Biol 5(8);575-7. PMID: 19483696
Chen03a: Chen S, Glawischnig E, Jorgensen K, Naur P, Jorgensen B, Olsen CE, Hansen CH, Rasmussen H, Pickett JA, Halkier BA (2003). "CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis." Plant J 33(5);923-37. PMID: 12609033
Douglas04: Douglas Grubb C, Zipp BJ, Ludwig-Muller J, Masuno MN, Molinski TF, Abel S (2004). "Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis." Plant J 40(6);893-908. PMID: 15584955
Hansen01: Hansen CH, Wittstock U, Olsen CE, Hick AJ, Pickett JA, Halkier BA (2001). "Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates." J Biol Chem 276(14);11078-85. PMID: 11133994
Hansen08: Hansen BG, Kerwin RE, Ober JA, Lambrix VM, Mitchell-Olds T, Gershenzon J, Halkier BA, Kliebenstein DJ (2008). "A novel 2-oxoacid-dependent dioxygenase involved in the formation of the goiterogenic 2-hydroxybut-3-enyl glucosinolate and generalist insect resistance in Arabidopsis,." Plant Physiol 148(4);2096-108. PMID: 18945935
Klein06: Klein M, Reichelt M, Gershenzon J, Papenbrock J (2006). "The three desulfoglucosinolate sulfotransferase proteins in Arabidopsis have different substrate specificities and are differentially expressed." FEBS J 273(1);122-36. PMID: 16367753
Kliebenstein01: Kliebenstein DJ, Lambrix VM, Reichelt M, Gershenzon J, Mitchell-Olds T (2001). "Gene duplication in the diversification of secondary metabolism: tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis." Plant Cell 13(3);681-93. PMID: 11251105
Knill08: Knill T, Schuster J, Reichelt M, Gershenzon J, Binder S (2008). "Arabidopsis branched-chain aminotransferase 3 functions in both amino acid and glucosinolate biosynthesis." Plant Physiol 146(3);1028-39. PMID: 18162591
Mikkelsen04: Mikkelsen MD, Naur P, Halkier BA (2004). "Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis." Plant J 37(5);770-7. PMID: 14871316
Naur03: Naur P, Petersen BL, Mikkelsen MD, Bak S, Rasmussen H, Olsen CE, Halkier BA (2003). "CYP83A1 and CYP83B1, Two Nonredundant Cytochrome P450 Enzymes Metabolizing Oximes in the Biosynthesis of Glucosinolates in Arabidopsis." Plant Physiol 133(1);63-72. PMID: 12970475
Piotrowski04: Piotrowski M, Schemenewitz A, Lopukhina A, Muller A, Janowitz T, Weiler EW, Oecking C (2004). "Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure." J Biol Chem 279(49);50717-25. PMID: 15358770
Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216
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