Information on EC 1.14.13.85 - glyceollin synthase

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The expected taxonomic range for this enzyme is: Glycine max

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EC NUMBER
COMMENTARY hide
1.14.13.85
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RECOMMENDED NAME
GeneOntology No.
glyceollin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADPH + H+ + O2 = glyceollin + NADP+ + 2 H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclization
-
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oxidation
-
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glyceollin biosynthesis
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Isoflavonoid biosynthesis
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-
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SYSTEMATIC NAME
IUBMB Comments
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan,NADPH:oxygen oxidoreductase (cyclizing)
A heme-thiolate protein (P-450). Glyceollins II and III are formed from 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan whereas glyceollin I is formed from the 4-isomer.
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CAS REGISTRY NUMBER
COMMENTARY hide
115110-88-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cv. Harosoy 63
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-
Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADPH + H+ + O2
glyceollin + NADP+ + 2 H2O
show the reaction diagram
-
enzyme catalyzes an NADPH-dependent and oxygen-dependent cyclization of a mixture of 2- and 4-dimethylallylglycinols to the glyceollin isomers I-III
glyceollin isomers I-III, glyceollin isomer I is formed from 4-dimethylallylglycinol and glyceollin isomers II and III from 2-dimethylallylglycinol
-
?
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
additional information
?
-
-
last committed step in the glyceollin biosynthesis
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-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b
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average content of b-type cytochromes: 0.26 nmol/mg protein
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cytochrome P-450
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cytochrome P-450-dependent monooxygenase, average content of cytochrome P-450: 0.16 nmol/mg protein
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NADPH
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NADPH-dependent, absolute requirement
O2
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oxygen-dependent
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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0.01 mM: 15% inhibition, 0.1 mM: 85% inhibition
BAS 110
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0.1 mM, 15% inhibition
BAS 111
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0.1 mM, 39% inhibition
CO
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inhibits in a white light-reversible manner in the presence of oxygen
cytochrome c
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0.01 mM: 25% inhibition, 0.025 mM: 64% inhibition, 0.05 mM: 85% inhibition
glyceollin
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product inhibition, 0.058 mM, 50% inhibition
ketoconazol
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0.01 mM: 34% inhibition, 0.1 mM: 100% inhibition
LAB 978
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0.01 mM: 17% inhibition, 0.1 mM: 49% inhibition
Metyrapone
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0.01 mM: 15% inhibition, 0.1 mM: 37% inhibition
NADP+
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strong inhibition by NADP+ at low NADPH concentrations
potassium isothiocyanate
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0.01 mM: 19% inhibition, 0.1 mM: 73% inhibition, 1 mM: 100% inhibition
SKF 525
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0.1 mM: 11% inhibition, 1 mM: 100% inhibition
tetcyclasis
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0.01 mM: 9% inhibition, 0.1 mM: 67% inhibition
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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a synergistic effect of NADH, 94% increase in cyclase activity, is observed at low NADPH concentrations of about 0.01 mM
additional information
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challenge with either a glucan elicitor from Phytophthora megasperma f.sp. glycinea or with yeast extract causes strong stimulation of cyclase activity with a maximum at about 24 h after elicitor addition
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan
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pH 7.5, 20°C, mixture of the two glyceollidin isomers
0.03
perrhenate
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pH 7.5, 20°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 9.5
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very broad pH-optimum
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9.5
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pH 7: 50% of maximum activity, no activity measurable above pH 9.5, probably because of the instability of the substrate
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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assay at
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
elicitor-challenged, unstimulated cell culture does not contain detectable cyclase activity
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
the cyclase is associated with
Manually annotated by BRENDA team
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.85)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)