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EC Tree
IUBMB Comments Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization and lactonization to form scopoletin, liberating CoA in the process. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-4-coumaroyl-CoA. cf. EC 1.14.11.62, trans-4-coumaroyl-CoA 2-hydroxylase.
The enzyme appears in viruses and cellular organisms
Synonyms
f6'h1, cyp98a22, feruloyl-coa 6'-hydroxylase 1,
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feruloyl CoA ortho-hydroxylase 1
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feruloyl-CoA 6'-hydroxylase 1
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trans-feruloyl-CoA + 2-oxoglutarate + O2 = trans-6-hydroxyferuloyl-CoA + succinate + CO2
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feruloyl-CoA,2-oxoglutarate:oxygen oxidoreductase (6-hydroxylating)
Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization and lactonization to form scopoletin, liberating CoA in the process. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-4-coumaroyl-CoA. cf. EC 1.14.11.62, trans-4-coumaroyl-CoA 2-hydroxylase.
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caffeoyl-CoA + 2-oxoglutarate + O2
6'-hydroxycaffeoyl-CoA + succinate + CO2
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trans-4-coumaroyl-CoA + 2-oxoglutarate + O2
2,4-dihydroxycinnamoyl-CoA + succinate + CO2
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trans-feruloyl-CoA + 2-oxoglutarate + O2
trans-6-hydroxyferuloyl-CoA + succinate + CO2
additional information
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trans-feruloyl-CoA + 2-oxoglutarate + O2
trans-6-hydroxyferuloyl-CoA + succinate + CO2
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trans-feruloyl-CoA + 2-oxoglutarate + O2
trans-6-hydroxyferuloyl-CoA + succinate + CO2
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trans-feruloyl-CoA + 2-oxoglutarate + O2
trans-6-hydroxyferuloyl-CoA + succinate + CO2
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additional information
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trace reactions with p-coumaroyl CoA, no substrate: ferulic acid, feruloylquinic acid, caffeic acid, caffeoyl CoA, p-coumaric acid, cinnamic acid, cinnamoyl CoA, benzoyl CoA
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additional information
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trace reactions with p-coumaroyl CoA, no substrate: ferulic acid, feruloylquinic acid, caffeic acid, caffeoyl CoA, p-coumaric acid, cinnamic acid, cinnamoyl CoA, benzoyl CoA
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no substrates: cinnamoyl-CoA and the respective free acids
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additional information
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no substrates: cinnamoyl-CoA and the respective free acids
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additional information
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no substrates: cinnamic acid, caffeic acid, p-coumaric acid, ferulic acid, cinnamoyl-CoA, caffeoyl-CoA
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trans-feruloyl-CoA + 2-oxoglutarate + O2
trans-6-hydroxyferuloyl-CoA + succinate + CO2
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additional information
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additional information
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trace reactions with p-coumaroyl CoA, no substrate: ferulic acid, feruloylquinic acid, caffeic acid, caffeoyl CoA, p-coumaric acid, cinnamic acid, cinnamoyl CoA, benzoyl CoA
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additional information
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trace reactions with p-coumaroyl CoA, no substrate: ferulic acid, feruloylquinic acid, caffeic acid, caffeoyl CoA, p-coumaric acid, cinnamic acid, cinnamoyl CoA, benzoyl CoA
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0.0092 - 0.037
trans-feruloyl-CoA
0.0092
trans-feruloyl-CoA
pH 6.5, 30°C
0.0102
trans-feruloyl-CoA
pH 6.5, 30°C
0.036
trans-feruloyl-CoA
30°C, pH 6.5
0.037
trans-feruloyl-CoA
pH 7.2, 30°C
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2.68 - 11
trans-feruloyl-CoA
2.68
trans-feruloyl-CoA
pH 6.5, 30°C
2.84
trans-feruloyl-CoA
pH 6.5, 30°C
11
trans-feruloyl-CoA
30°C, pH 6.5
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0.013
trans-feruloyl-CoA
pH 7.2, 30°C
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0.122
psoralen
pH 7.2, 30°C
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UniProt
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UniProt
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bifunctional enzyme, catalyzes the activities of EC 1.14.11.61 and EC 1.14.11.62 with equal activities
UniProt
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isoform F6H1-2
UniProt
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isoform F6H1-3
UniProt
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expression is induced by UV light
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expression is induced by UV light
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physiological function
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biosynthetic steps of scopoletin synthesis in roots suffering from post-harvest physiological deterioration, when secondary metabolites accumulate. Amongst these are hydroxycoumarins which play roles in plant defence and have pharmacological activities
physiological function
enzyme is involved in scopoletin synthesis. Young leaves Nicotiana attenuata, are more resistant to Alternaria alternata infection than mature leaves, and this is correlated with stronger blue fluorescence emitted by scopoletin and its beta-glycoside form, scopolin. Silencing of F6'H1 reduces scopoletin levels and plant resistance against Alternaria alternata
physiological function
T-DNA insertion mutants of F6'H1 show severe reductions in scopoletin and scopolin levels in the roots. The pattern of F6'H1 expression is consistent with the patterns of scopoletin and scopolin accumulation
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structure of apo enzyme, space group C2, with unit-cell parameters a 193.22 A, b 54.55 A, c 78.82 A and gamma 111.5°
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expression in Escherichia coli
expression in Escherichia coli and Nicotiana benthamiana
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expression is induced by jasmonic acid
in leaf and petiole, expression is induced by UV light
silencing MYC2, a master regulator of most jasmonic acid responses, reduces Alternaria alternata-induced NaF6'H1 transcripts and scopoletin level
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Sun, H.; Wang, L.; Zhang, B.; Ma, J.; Hettenhausen, C.; Cao, G.; Sun, G.; Wu, J.; Wu, J.
Scopoletin is a phytoalexin against Alternaria alternata in wild tobacco dependent on jasmonate signalling
J. Exp. Bot.
65
4305-4315
2014
Nicotiana attenuata (A0A089RN78), Nicotiana attenuata
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Bayoumi, S.; Rowan, M.; Blagbrough, I.; Beeching, J.
Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration The E-Z-isomerisation stage
Phytochemistry
69
2928-2936
2008
Manihot esculenta
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Matsumoto, S.; Mizutani, M.; Sakata, K.; Shimizu, B.
Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam
Phytochemistry
74
49-57
2012
Ipomoea batatas (G9M9M1), Ipomoea batatas (G9M9M2)
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Kai, K.; Mizutani, M.; Kawamura, N.; Yamamoto, R.; Tamai, M.; Yamaguchi, H.; Sakata, K.; Shimizu, B.
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana
Plant J.
55
989-999
2008
Arabidopsis thaliana (Q9LHN8), Arabidopsis thaliana
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Vialart, G.; Hehn, A.; Olry, A.; Ito, K.; Krieger, C.; Larbat, R.; Paris, C.; Shimizu, B.; Sugimoto, Y.; Mizutani, M.; Bourgaud, F.
A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. Exhibits p-coumaroyl CoA 2-hydroxylase activity (C2H) A missing step in the synthesis of umbelliferone in plants
Plant J.
70
460-470
2012
Ruta graveolens (H9LJF9)
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Sun, X.; Zhou, D.; Kandavelu, P.; Zhang, H.; Yuan, Q.; Wang, B.; Rose, J.; Yan, Y.
Structural insights into substrate specificity of feruloyl-CoA 6-hydroxylase from Arabidopsis thaliana
Sci. Rep.
5
10355
2015
Arabidopsis thaliana (Q9LHN8), Arabidopsis thaliana
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1.14.11.61 feruloyl-CoA 6-hydroxylase
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