MetaCyc Pathway: glucosinolate biosynthesis from pentahomomethionine
Inferred from experiment

Pathway diagram: glucosinolate biosynthesis from pentahomomethionine

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisNitrogen-Containing Secondary Compounds BiosynthesisNitrogen-Containing Glucosides BiosynthesisGlucosinolates 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].

Citations: [Sonderby10]

Created 23-Jul-2009 by Zhang P, TAIR
Revised 29-Apr-2010 by Zhang P


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

Li08: Li J, Hansen BG, Ober JA, Kliebenstein DJ, Halkier BA (2008). "Subclade of flavin-monooxygenases involved in aliphatic glucosinolate biosynthesis." Plant Physiol 148(3);1721-33. PMID: 18799661

Sonderby10: Sonderby IE, Geu-Flores F, Halkier BA (2010). "Biosynthesis of glucosinolates - gene discovery and beyond." Trends Plant Sci. PMID: 20303821

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

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

Hansen01a: 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

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

Klein09: Klein M, Papenbrock J (2009). "Kinetics and substrate specificities of desulfo-glucosinolate sulfotransferases in Arabidopsis thaliana." Physiol Plant 135(2);140-9. PMID: 19077143

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

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

Textor04: Textor S, Bartram S, Kroymann J, Falk KL, Hick A, Pickett JA, Gershenzon J (2004). "Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle." Planta 218(6);1026-35. PMID: 14740211

Wittstock02: Wittstock U, Halkier BA (2002). "Glucosinolate research in the Arabidopsis era." Trends Plant Sci 2002;7(6);263-70. PMID: 12049923

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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