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Literature summary for 1.14.14.135 extracted from

  • Welle, R.; Grisebach, H.
    Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers (1988), Arch. Biochem. Biophys., 263, 191-198.
    View publication on PubMed

Activating Compound

Activating Compound Comment Organism Structure
additional information 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 Glycine max
NADH a synergistic effect of NADH, 94% increase in cyclase activity, is observed at low NADPH concentrations of about 0.01 mM Glycine max

Inhibitors

Inhibitors Comment Organism Structure
Ancymidol 0.01 mM: 15% inhibition, 0.1 mM: 85% inhibition Glycine max
BAS 110 0.1 mM, 15% inhibition Glycine max
BAS 111 0.1 mM, 39% inhibition Glycine max
CO inhibits in a white light-reversible manner in the presence of oxygen Glycine max
cytochrome c 0.01 mM: 25% inhibition, 0.025 mM: 64% inhibition, 0.05 mM: 85% inhibition Glycine max
glyceollin product inhibition, 0.058 mM, 50% inhibition Glycine max
ketoconazol 0.01 mM: 34% inhibition, 0.1 mM: 100% inhibition Glycine max
LAB 978 0.01 mM: 17% inhibition, 0.1 mM: 49% inhibition Glycine max
Metyrapone 0.01 mM: 15% inhibition, 0.1 mM: 37% inhibition Glycine max
NADP+ strong inhibition by NADP+ at low NADPH concentrations Glycine max
potassium isothiocyanate 0.01 mM: 19% inhibition, 0.1 mM: 73% inhibition, 1 mM: 100% inhibition Glycine max
SKF 525 0.1 mM: 11% inhibition, 1 mM: 100% inhibition Glycine max
tetcyclasis 0.01 mM: 9% inhibition, 0.1 mM: 67% inhibition Glycine max

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.002
-
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan pH 7.5, 20°C, mixture of the two glyceollidin isomers Glycine max
0.03
-
perrhenate pH 7.5, 20°C Glycine max

Localization

Localization Comment Organism GeneOntology No. Textmining
endoplasmic reticulum the cyclase is associated with Glycine max 5783
-
microsome
-
Glycine max
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Glycine max last committed step in the glyceollin biosynthesis ?
-
?

Organism

Organism UniProt Comment Textmining
Glycine max
-
cv. Harosoy 63
-

Reaction

Reaction Comment Organism Reaction ID
2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin II + [oxidized NADPH-hemoprotein reductase] + 2 H2O 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 Glycine max

Source Tissue

Source Tissue Comment Organism Textmining
cell suspension culture elicitor-challenged, unstimulated cell culture does not contain detectable cyclase activity Glycine max
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
additional information
-
-
Glycine max

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 enzyme catalyzes an NADPH-dependent and oxygen-dependent cyclization of a mixture of 2- and 4-dimethylallylglycinols to the glyceollin isomers I-III Glycine max glyceollin + [oxidized NADPH-hemoprotein reductase] + H2O glyceollin isomers I-III, glyceollin isomer I is formed from 4-dimethylallylglycinol and glyceollin isomers II and III from 2-dimethylallylglycinol ?
glyceollin II + NADPH + H+ + H2O
-
Glycine max 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADP+ + O2
-
r
additional information last committed step in the glyceollin biosynthesis Glycine max ?
-
?
additional information not: NADH, enzyme does not catalyze the conversion of rot-2-enoic acid to deguelin in the presence or absence of NADPH Glycine max ?
-
?

Synonyms

Synonyms Comment Organism
dimethylallyl-3,6a,9-trihydroxypterocarpan cyclase
-
Glycine max

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
20
-
assay at Glycine max

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5 9.5 very broad pH-optimum Glycine max

pH Range

pH Minimum pH Maximum Comment Organism
7 9.5 pH 7: 50% of maximum activity, no activity measurable above pH 9.5, probably because of the instability of the substrate Glycine max

Cofactor

Cofactor Comment Organism Structure
cytochrome b average content of b-type cytochromes: 0.26 nmol/mg protein Glycine max
cytochrome P-450 cytochrome P-450-dependent monooxygenase, average content of cytochrome P-450: 0.16 nmol/mg protein Glycine max
O2 oxygen-dependent Glycine max