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Literature summary extracted from

  • Clausen, M.; Kannangara, R.M.; Olsen, C.E.; Blomstedt, C.K.; Gleadow, R.M.; Jorgensen, K.; Bak, S.; Motawie, M.S.; Moller, B.L.
    The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways (2015), Plant J., 84, 558-573.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.36 expression in Nicotiana tabacum Sorghum bicolor
1.14.14.37 expression in Nicotiana tabacum Sorghum bicolor

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.36 membrane
-
Sorghum bicolor 16020
-
1.14.14.37 membrane
-
Sorghum bicolor 16020
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.36 L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase] Sorghum bicolor
-
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O overall reaction ?
1.14.14.36 L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase] Sorghum bicolor
-
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.36 N,N-dihydroxy-L-tyrosine Sorghum bicolor
-
(E)-[4-hydroxyphenylacetaldehyde oxime] + CO2 + H2O
-
?
1.14.14.36 N-hydroxy-L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase] Sorghum bicolor
-
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.37 (E)-4-Hydroxyphenylacetaldehyde oxime Sorghum bicolor
-
(Z)-4-Hydroxyphenylacetaldehyde oxime
-
?
1.14.14.37 (E)-4-hydroxyphenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 Sorghum bicolor
-
(S)-4-hydroxymandelonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O overall reaction ?
1.14.14.37 (Z)-4-hydroxyphenylacetaldehyde oxime Sorghum bicolor
-
4-hydroxyphenylacetonitrile + H2O
-
?
1.14.14.37 4-hydroxyphenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 Sorghum bicolor
-
(S)-4-hydroxymandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.40 (E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase] Sorghum bicolor
-
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase] first step of reaction ?
1.14.14.40 1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol Sorghum bicolor
-
(Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O
-
?
1.14.14.40 an (E)-omega-(methylthio)alkanal oxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase] Sorghum bicolor
-
an (E)-1-(glutathione-S-yl)-omega-(methylthio)alkylhydroximate + 2 H2O + [oxidized NADPH-hemoprotein reductase] overall reaction ?
1.14.14.40 additional information Sorghum bicolor CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis ?
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.36 Sorghum bicolor Q43135
-
-
1.14.14.37 Sorghum bicolor O48958
-
-
1.14.14.40 Sorghum bicolor
-
-
-
1.14.14.45 Arabidopsis thaliana O65782
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.36 L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor (E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O overall reaction ?
1.14.14.36 L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.36 N,N-dihydroxy-L-tyrosine
-
Sorghum bicolor (E)-[4-hydroxyphenylacetaldehyde oxime] + CO2 + H2O
-
?
1.14.14.36 N-hydroxy-L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.37 (E)-4-Hydroxyphenylacetaldehyde oxime
-
Sorghum bicolor (Z)-4-Hydroxyphenylacetaldehyde oxime
-
?
1.14.14.37 (E)-4-hydroxyphenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2
-
Sorghum bicolor (S)-4-hydroxymandelonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O overall reaction ?
1.14.14.37 (Z)-4-hydroxyphenylacetaldehyde oxime
-
Sorghum bicolor 4-hydroxyphenylacetonitrile + H2O
-
?
1.14.14.37 4-hydroxyphenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2
-
Sorghum bicolor (S)-4-hydroxymandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
-
?
1.14.14.40 (E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor 1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase] first step of reaction ?
1.14.14.40 1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol
-
Sorghum bicolor (Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O
-
?
1.14.14.40 an (E)-omega-(methylthio)alkanal oxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor an (E)-1-(glutathione-S-yl)-omega-(methylthio)alkylhydroximate + 2 H2O + [oxidized NADPH-hemoprotein reductase] overall reaction ?
1.14.14.40 additional information CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis Sorghum bicolor ?
-
?
1.14.14.40 tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
-
Sorghum bicolor (E)-4-hydroxyphenylacetaldoxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O overall reaction, CYP79A1 catalyzes the specific production of (E)-phydroxyphenylacetaldoxime ?
1.14.14.45 (E)-p-hydroxyphenylacetaldoxime + NADPH + H+ + 2-mercaptoethanol
-
Arabidopsis thaliana (Z)-2-hydroxyethyl N,4-dihydroxybenzene-1-carboximidothioate + NADP+ + H2O CYP83B1 shows absolute specificity towards (E)-p-hydroxyphenylacetaldoxime as a substrate, and the (Z)-S-alkyl-thiohydroximate formed maintains the structural configuration of the oxime function as in the (E)-p-hydroxyphenylacetaldoxime substrate ?
1.14.14.45 additional information CYP83B1 cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure Arabidopsis thaliana ?
-
?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.40 CYP79A1
-
Sorghum bicolor

General Information

EC Number General Information Comment Organism
1.14.14.36 physiological function the biosynthetic pathway for the cyanogenic glucoside dhurrin in Sorghum involves the sequential production of (E)- and (Z)-4-hydroxyphenylacetaldoxime. Monooxygenae CYP79A1 catalyzes conversion of tyrosine to (E)-4-hydroxyphenylacetaldoxime, whereas monooxygenase CYP71E1 catalyzes conversion of (E)-4-hydroxyphenylacetaldoxime into the corresponding geometrical Z-isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis Sorghum bicolor
1.14.14.37 physiological function the biosynthetic pathway for the cyanogenic glucoside dhurrin in Sorghum involves the sequential production of (E)- and (Z)-4-hydroxyphenylacetaldoxime. Monooxygenae CYP79A1 catalyzes conversion of tyrosine to (E)-4-hydroxyphenylacetaldoxime, whereas monooxygenase CYP71E1 catalyzes conversion of (E)-4-hydroxyphenylacetaldoxime into the corresponding geometrical Z-isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis Sorghum bicolor