ENTRY ko00966 Pathway NAME Glucosinolate biosynthesis DESCRIPTION Glucosinolates are biologically active secondary metabolites found in Brassicaceae (mustard family) and related families.These compounds are genetically variable within plant species and used as natural pesticides, such as against insect herbivores. All glucosinolates share a common structure consisting of a beta-thioglucose moiety, a sulfonated oxime moiety, and a variable aglycone side chain derived from an alpha-amino acid. Genes encoding glucosinolate biosynthetic enzymes have been identified in Arabidopsis thaliana by genetic polymorphisms and loss-of-function mutations. This map shows examples of side chain elongation in methionine-derived glucosinolates and the core pathway for biosynthesis of glucosinolates from amino acids. CLASS Metabolism; Biosynthesis of other secondary metabolites PATHWAY_MAP ko00966 Glucosinolate biosynthesis MODULE M00370 Glucosinolate biosynthesis, tryptophan => glucobrassicin [PATH:ko00966] DBLINKS GO: 0019761 ORTHOLOGY K21346 methionine transaminase [EC:2.6.1.88] K15741 methylthioalkylmalate synthase 1 [EC:2.3.3.17] K15742 methylthioalkylmalate synthase 3 [EC:2.3.3.17] K01703 3-isopropylmalate/(R)-2-methylmalate dehydratase large subunit [EC:4.2.1.33 4.2.1.35] K21359 3-isopropylmalate/methylthioalkylmalate dehydratase small subunit [EC:4.2.1.33 4.2.1.170] K21360 3-isopropylmalate/methylthioalkylmalate dehydrogenase [EC:1.1.1.85 1.1.1.-] K00826 branched-chain amino acid aminotransferase [EC:2.6.1.42] K12154 homomethionine N-monooxygenase [EC:1.14.14.42] K12156 (methylthio)alkanaldoxime N-monooxygenase [EC:1.14.14.43] K11819 S-alkyl-thiohydroximate lyase SUR1 [EC:4.4.1.-] K11820 N-hydroxythioamide S-beta-glucosyltransferase [EC:2.4.1.195] K11821 aromatic desulfoglucosinolate sulfotransferase [EC:2.8.2.24] K22321 aliphatic desulfoglucosinolate sulfotransferase [EC:2.8.2.38] K12155 homomethionine N-monooxygenase [EC:1.14.14.42] K13401 valine N-monooxygenase [EC:1.14.14.38] K14984 isoleucine N-monooxygenase [EC:1.14.14.39] K12153 phenylalanine N-monooxygenase [EC:1.14.14.40] K11818 aromatic aldoxime N-monooxygenase [EC:1.14.14.45] K11812 tryptophan N-monooxygenase [EC:1.14.14.156] K11813 tryptophan N-monooxygenase [EC:1.14.14.156] K13027 tyrosine N-monooxygenase [EC:1.14.14.36] COMPOUND C00073 L-Methionine C00078 L-Tryptophan C00079 L-Phenylalanine C00082 L-Tyrosine C00123 L-Leucine C00141 3-Methyl-2-oxobutanoic acid C00183 L-Valine C00233 4-Methyl-2-oxopentanoate C00407 L-Isoleucine C00671 (S)-3-Methyl-2-oxopentanoic acid C01069 Desulfoglucotropeolin C01180 4-Methylthio-2-oxobutanoic acid C02153 Glucotropaeolin C02937 Indole-3-acetaldehyde oxime C03219 (E)-2-Methylpropanal oxime C03719 Phenylacetothiohydroximate C04350 (E)-4-Hydroxyphenylacetaldehyde oxime C05837 Glucobrassicin C08401 Glucoberteroin C08407 Glucocochlearin C08409 Glucoerucin C08412 Glucoiberverin C08417 Gluconasturtiin C08418 Glucoputranjivin C08426 Sinalbin C16516 Indolylmethylthiohydroximate C16517 Indolylmethyl-desulfoglucosinolate C16518 S-(Indolylmethylthiohydroximoyl)-L-cysteine C17210 2-(2'-Methylthio)ethylmalic acid C17211 2-Oxo-5-methylthiopentanoic acid C17212 3-(2'-Methylthio)ethylmalic acid C17213 Homomethionine C17214 2-(3'-Methylthio)propylmalic acid C17215 3-(3'-Methylthio)propylmalic acid C17216 2-Oxo-6-methylthiohexanoic acid C17217 Dihomomethionine C17218 2-(4'-Methylthio)butylmalic acid C17219 3-(4'-Methylthio)butylmalic acid C17220 2-Oxo-7-methylthioheptanoic acid C17221 Trihomomethionine C17222 2-(5'-Methylthio)pentylmalic acid C17223 3-(5'-Methylthio)pentylmalic acid C17224 2-Oxo-8-methylthiooctanoic acid C17225 Tetrahomomethionine C17226 2-(6'-Methylthio)hexylmalic acid C17227 3-(6'-Methylthio)hexylmalic acid C17228 2-Oxo-9-methylthiononanoic acid C17229 Pentahomomethionine C17230 2-(7'-Methylthio)heptylmalic acid C17231 3-(7'-Methylthio)heptylmalic acid C17232 2-Oxo-10-methylthiodecanoic acid C17233 Hexahomomethionine C17235 L-Homophenylalanine C17236 3-Phenylpropionaldoxim C17237 S-(Phenylacetothiohydroximoyl)-L-cysteine C17238 S-(Hydroxyphenylacetothiohydroximoyl)-L-cysteine C17239 p-Hydroxyphenylacetothiohydroximate C17240 p-Hydroxybenzyldesulphoglucosinolate C17241 4-Methylthiobutanaldoxime C17242 S-(4-Methylthiobutylthiohydroximoyl)-L-cysteine C17243 4-Methylthiobutylthiohydroximate C17244 3-Methylthiopropyl-desulfoglucosinolate C17245 5-Methylthiopentanaldoxime C17246 6-Methylthiohexanaldoxime C17248 4-Methylthiobutyl-desulfoglucosinolate C17249 7-Methylthioheptanaldoxime C17250 Glucolesquerellin C17251 8-Methylthiooctanaldoxime C17252 7-Methylthioheptyl glucosinolate C17253 9-Methylthiononanaldoxime C17254 8-Methylthiooctyl glucosinolate C17255 3-Methylbutyraldehyde oxime C17256 2-Methylpropyl glucosinolate C19491 (E)-2-Methylbutanal oxime C19714 (E)-Phenylacetaldoxime C21650 7-Methylthioheptyl-desulfoglucosinolate C21746 8-Methylthiooctyl-desulfoglucosinolate REFERENCE PMID:12049923 AUTHORS Wittstock U, Halkier BA TITLE Glucosinolate research in the Arabidopsis era. JOURNAL Trends Plant Sci 7:263-70 (2002) DOI:10.1016/S1360-1385(02)02273-2 REFERENCE PMID:15913672 AUTHORS Windsor AJ, Reichelt M, Figuth A, Svatos A, Kroymann J, Kliebenstein DJ, Gershenzon J, Mitchell-Olds T TITLE Geographic and evolutionary diversification of glucosinolates among near relatives of Arabidopsis thaliana (Brassicaceae). JOURNAL Phytochemistry 66:1321-33 (2005) DOI:10.1016/j.phytochem.2005.04.016 REFERENCE PMID:14740211 AUTHORS Textor S, Bartram S, Kroymann J, Falk KL, Hick A, Pickett JA, Gershenzon J TITLE Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle. JOURNAL Planta 218:1026-35 (2004) DOI:10.1007/s00425-003-1184-3 REFERENCE PMID:15358770 AUTHORS Piotrowski M, Schemenewitz A, Lopukhina A, Muller A, Janowitz T, Weiler EW, Oecking C TITLE Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. JOURNAL J Biol Chem 279:50717-25 (2004) DOI:10.1074/jbc.M407681200 REFERENCE PMID:12586901 AUTHORS Mikkelsen MD, Halkier BA TITLE Metabolic engineering of valine- and isoleucine-derived glucosinolates in Arabidopsis expressing CYP79D2 from Cassava. JOURNAL Plant Physiol 131:773-9 (2003) DOI:10.1104/pp.013425 REFERENCE AUTHORS Chen S, Andreasson E. TITLE Update on glucosinolate metabolism and transport. JOURNAL Plant Physiol Biochem 39:743-758 (2001) DOI:10.1016/S0981-9428(01)01301-8 REL_PATHWAY ko00270 Cysteine and methionine metabolism ko00290 Valine, leucine and isoleucine biosynthesis ko00400 Phenylalanine, tyrosine and tryptophan biosynthesis ///