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Information on EC 1.14.13.123 - germacrene A hydroxylase Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The enzyme appears in viruses and cellular organisms
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germacrene A hydroxylase
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(+)-germacrene A + NADPH + H+ + O2 = germacra-1(10),4,11(13)-trien-12-ol + NADP+ + H2O
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hydroxylation
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C13-hydroxylation
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Biosynthesis of secondary metabolites
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costunolide biosynthesis
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Sesquiterpenoid and triterpenoid biosynthesis
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(+)-germacrene-A,NADPH:oxygen oxidoreductase (12-hydroxylating)
A heme-thiolate protein (P-450). This is probably part of the biosynthesis of many sesquiterpenoid lactones. In Lactuca sativa EC 1.14.13.123 is a mutifunctional enzyme with EC 1.1.1.314, germacrene A alcohol dehydrogenase [2].
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(+)-germacrene A hydroxylase
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GAO
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germacrene A oxidase
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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UniProt
brenda
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brenda
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(+)-germacrene A + NADPH + H+ + O2
germacra-1(10),4,11(13)-trien-12-ol + NADP+ + H2O
beta-elemene + NADPH + H+ + O2
elema-1,3,11(13)-trien-12-ol + NADP+ + H2O
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the amount of (+)-beta-elemene hydroxylated is 2times less than that of (-)-beta-elemene
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?
germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
(+)-germacrene A + NADPH + H+ + O2
germacra-1(10),4,11(13)-trien-12-ol + NADP+ + H2O
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100% activity
germacra-1(10),4,11(13)-trien-12-ol is also named costol
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(+)-germacrene A + NADPH + H+ + O2
germacra-1(10),4,11(13)-trien-12-ol + NADP+ + H2O
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30% activity with NADH as compared to NADPH
germacra-1(10),4,11(13)-trien-12-ol is also named costol
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germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
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germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
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germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
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germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
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germacrene A + NADPH + H+ + O2
12-hydroxygermacrene A + NADP+ + H2O
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flavin
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an assay buffer without flavins (FAD and FMN) gives 18% loss of hydroxylase activity. However, omitting these flavins from the extraction buffer results in a loss of more than 70% in enzyme activity
NADH
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NADH is 60% less efficient as a reductant than NADPH
NADPH
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NADPH
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required for activity, the combination of NADPH with NADH shows an additive effect on enzyme activity (120%)
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aminobenzotriazole
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26% inhibition at 0.1 mM
carbon monoxide
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blue-light reversible inhibition, an atmosphere of 80% CO plus 20% O2 inhibits (+)-germacrene A hydroxylase by 69%
clotrimazole
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016% inhibition at 0.1 mM
cytochrome c
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97% inhibition at 0.1 mM
Metyrapone
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23% inhibition at 1 mM
miconazole
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30% inhibition at 0.1 mM
additional information
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flushing the reaction mixture for 1.5 min with argon prior to incubation causes a 69% decrease of enzyme activity because of O2 depletion
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6 - 9
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60% of maximal enzyme activity at pH 7.5 and 9.0 (no difference in activity between bis-Tris and Tris buffer)
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brenda
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54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
54900
calculated from amino acid sequence
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expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
expressed in the protease-deficient Saccharomyces cerevisiae YPL 154C:Pep4 KO strain
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GAO_SAUCO
488
55032
Swiss-Prot
GAO_CICIN
488
54972
Swiss-Prot
GAO_LACSA
488
54963
Swiss-Prot
GAO_HELAN
488
55088
Swiss-Prot
GAO_BARSP
496
55699
Swiss-Prot
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Nguyen, D.; Goepfert, J.; Ikezawa, N.; MacNevin, G.; Kathiresan, M.; Conrad, J.; Spring, O.; Ro, D.
Biochemical conservation and evolution of germacrene A oxidase in Asteraceae
J. Biol. Chem.
285
16588-16598
2010
Barnadesia spinosa (D5JBX1), Cichorium intybus (D5JBW8), Helianthus annuus (D5JBX0), Lactuca sativa (D5J9U8), Saussurea costus (D5JBW9)
brenda
De Kraker, K.J.; Franssen, M.; Dalm, M.; de, G.A.; Bouwmeester, H.
Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis
Plant Physiol.
125
1930-1940
2001
Cichorium intybus
brenda
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