Information on EC 1.14.14.150 - costunolide synthase

for references in articles please use BRENDA:EC1.14.14.150
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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.150
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RECOMMENDED NAME
GeneOntology No.
costunolide synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate = (+)-costunolide + H2O
show the reaction diagram
(1c), spontaneous
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germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 = (+)-costunolide + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
overall reaction
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germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2 = 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Sesquiterpenoid and triterpenoid biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
germacra-1(10),4,11(13)-trien-12-oate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (6alpha-hydroxylating)
A heme-thiolate protein (P-450). The enzyme hydroxylates carbon C-6 of germacra-1(10),4,11(13)-trien-12-oate to give 6alpha-hydroxygermacra-1(10),4,11(13)-trien-12-oate, which probably spontaneously cyclises to form the lactone ring.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cultivar HA300
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Manually annotated by BRENDA team
cultivar Mariska
UniProt
Manually annotated by BRENDA team
cv. Zardband
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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the enzyme is one of the key players in the parthenolide biosynthesis, pathway overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH—hemoprotein reductase] + 2 H2O
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
germacra-1(10),4,11(13)-trien-12-oate + [reduced NADPH-hemoprotein reductase] + O2
(+)-costunolide + [oxidized NADPH—hemoprotein reductase] + 2 H2O
show the reaction diagram
additional information
?
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(+)-costunolide synthase is a cytochrome P450 enzyme
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH-hemoprotein reductase
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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required for parthenolide biosynthesis in plants, activates the enzyme
Mn2+
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required for parthenolide biosynthesis in plants, activates the enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CO
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the inhibition in the presence of 90% (v/v) CO and 10% (v/v) O2 is reversed to some extent by irradiation with blue light (450 nm)
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
COS expression analysis in plants with Mg2+ or Mn2+ feeding or without, overview
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expressed in Saccharomyces cerevisiae strain EPY300
expressed in yeast cells and in Nicotiana benthamiana leaves
gene CYP71Bl5, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, transient expression in Nicotiana benthamiana leaves via Agrobacterium tumefaciens strain AGL0 electrotransformation leading to production of costunolide in tabacco leaves determined as costunolide-cysteine and costunolide-glutathione