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Information on EC 1.14.14.147 - 3-epi-6-deoxocathasterone 23-monooxygenase for references in articles please use BRENDA:EC1.14.14.147
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EC Tree
IUBMB Comments A cytochrome P-450 (heme-thiolate) protein involved in brassinosteroid biosynthesis. C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol .
The expected taxonomic range for this enzyme is: Arabidopsis thaliana
Synonyms
CYP90C1, CYP90C1/ROTUNDIFOLIA3, CYP90D1, cytochrome P450 90C1, ROT3,
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ROT3
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rotundifolia3, gene name
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(22S,24R)-22-hydroxy-5alpha-ergostan-3-one + [reduced NADPH-hemoprotein reductase] + O2 = 3-dehydro-6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
(2)
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3-epi-6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2 = 6-deoxotyphasterol + [oxidized NADPH-hemoprotein reductase] + H2O
(1)
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3-epi-6-deoxocathasterone,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (C-23-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein involved in brassinosteroid biosynthesis. C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol [1].
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(22S)-22-hydroxycampest-4-en-3-one + [reduced NADPH-hemoprotein reductase] + O2
(22R,23R)-22,23-dihydroxycampest-4-en-3-one + [oxidized NADPH-hemoprotein reductase] + H2O
(22S)-22-hydroxycampesterol + [reduced NADPH-hemoprotein reductase] + O2
(22R,23R)-22,23-dihydroxycampesterol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one + [reduced NADPH-hemoprotein reductase] + O2
3-dehydro-6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
3-epi-6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2
6-deoxotyphasterol + [oxidized NADPH-hemoprotein reductase] + H2O
6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2
6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
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-
?
typhasterol + [reduced NADPH-hemoprotein reductase] + O2
castasterone + [oxidized NADPH-hemoprotein reductase] + H2O
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-
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-
?
(22S)-22-hydroxycampest-4-en-3-one + [reduced NADPH-hemoprotein reductase] + O2
(22R,23R)-22,23-dihydroxycampest-4-en-3-one + [oxidized NADPH-hemoprotein reductase] + H2O
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-
?
(22S)-22-hydroxycampest-4-en-3-one + [reduced NADPH-hemoprotein reductase] + O2
(22R,23R)-22,23-dihydroxycampest-4-en-3-one + [oxidized NADPH-hemoprotein reductase] + H2O
i.e. (22S,24R)-22-hydroxyergost-4-en-3-one
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-
?
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one + [reduced NADPH-hemoprotein reductase] + O2
3-dehydro-6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one + [reduced NADPH-hemoprotein reductase] + O2
3-dehydro-6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
i.e (22S)-22-hydroxycampest-4-en-3-one. C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol
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-
?
3-epi-6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2
6-deoxotyphasterol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
?
3-epi-6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2
6-deoxotyphasterol + [oxidized NADPH-hemoprotein reductase] + H2O
C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol
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?
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(22S,24R)-22-hydroxy-5alpha-ergostan-3-one + [reduced NADPH-hemoprotein reductase] + O2
3-dehydro-6-deoxoteasterone + [oxidized NADPH-hemoprotein reductase] + H2O
Q9M066
i.e (22S)-22-hydroxycampest-4-en-3-one. C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol
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-
?
3-epi-6-deoxocathasterone + [reduced NADPH-hemoprotein reductase] + O2
6-deoxotyphasterol + [oxidized NADPH-hemoprotein reductase] + H2O
Q9M066
C-23 hydroxylation shortcuts bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5alpha-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol
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-
?
typhasterol + [reduced NADPH-hemoprotein reductase] + O2
castasterone + [oxidized NADPH-hemoprotein reductase] + H2O
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?
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0.00494 - 0.77
(22S)-22-hydroxycampest-4-en-3-one
0.0181 - 0.0194
(22S)-22-hydroxycampesterol
0.00861 - 0.73
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
0.00106 - 0.00661
3-epi-6-deoxocathasterone
0.0169 - 0.0359
6-deoxocathasterone
0.00494
(22S)-22-hydroxycampest-4-en-3-one
pH 7.3, 30°C
0.77
(22S)-22-hydroxycampest-4-en-3-one
pH 7.3, 30°C, enzyme CYP90D1
0.0181
(22S)-22-hydroxycampesterol
pH 7.3, 30°C, enzyme CYP90D1
0.0194
(22S)-22-hydroxycampesterol
pH 7.3, 30°C
0.00861
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
pH 7.3, 30°C
0.73
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
pH 7.3, 30°C, enzyme CYP90D1
0.00106
3-epi-6-deoxocathasterone
pH 7.3, 30°C, enzyme CYP90D1
0.00661
3-epi-6-deoxocathasterone
pH 7.3, 30°C
0.0169
6-deoxocathasterone
pH 7.3, 30°C, enzyme CYP90D1
0.0359
6-deoxocathasterone
pH 7.3, 30°C
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0.017 - 0.023
(22S)-22-hydroxycampest-4-en-3-one
0.0018 - 0.002
(22S)-22-hydroxycampesterol
0.021 - 0.046
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
0.018 - 0.05
3-epi-6-deoxocathasterone
0.0023 - 0.0048
6-deoxocathasterone
0.017
(22S)-22-hydroxycampest-4-en-3-one
pH 7.3, 30°C, enzyme CYP90D1
0.023
(22S)-22-hydroxycampest-4-en-3-one
pH 7.3, 30°C
0.0018
(22S)-22-hydroxycampesterol
pH 7.3, 30°C
0.002
(22S)-22-hydroxycampesterol
pH 7.3, 30°C, enzyme CYP90D1
0.021
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
pH 7.3, 30°C, enzyme CYP90D1
0.046
(22S,24R)-22-hydroxy-5alpha-ergostan-3-one
pH 7.3, 30°C
0.018
3-epi-6-deoxocathasterone
pH 7.3, 30°C, enzyme CYP90D1
0.05
3-epi-6-deoxocathasterone
pH 7.3, 30°C
0.0023
6-deoxocathasterone
pH 7.3, 30°C
0.0048
6-deoxocathasterone
pH 7.3, 30°C, enzyme CYP90D1
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UniProt
brenda
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brenda
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metabolism
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the enzyme catalyses C-23 hydroxylation of several brassinosteroids, phytohormones involved in, for example, organ growth, cell expansion, cell division, and responses to abiotic and biotic stresses
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C90C1_ARATH
524
1
59356
Swiss-Prot
C90D1_ARATH
491
1
56153
Swiss-Prot
A0A2P6PYR7_ROSCH
495
1
56165
TrEMBL
A0A2P6PT81_ROSCH
347
1
40113
TrEMBL
A0A396HP36_MEDTR
131
0
14605
TrEMBL
A0A396HLN1_MEDTR
236
1
26920
TrEMBL
A0A2P6RXZ1_ROSCH
487
1
55791
TrEMBL
A0A396HLM9_MEDTR
161
0
18828
TrEMBL
A0A2G9HE44_9LAMI
495
1
56736
TrEMBL
A0A072TNC8_MEDTR
474
1
54681
TrEMBL
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heterologous expression in the baculovirus/insect cell system; heterologous expression in the baculovirus/insect cell system
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Ohnishi, T.; Szatmari, A.M.; Watanabe, B.; Fujita, S.; Bancos, S.; Koncz, C.; Lafos, M.; Shibata, K.; Yokota, T.; Sakata, K.; Szekeres, M.; Mizutani M.
C-23 hydroxylation by Arabidopsis CYP90C1 and CYP90D1 reveals a novel shortcut in brassinosteroid biosynthesis
Plant Cell
18
3275-3288
2006
Arabidopsis thaliana, Arabidopsis thaliana (Q9M066)
brenda
Polko, J.K.; Pierik, R.; van Zanten, M.; Tarkowska, D.; Strnad, M.; Voesenek, L.A.; Peeters, A.J.
Ethylene promotes hyponastic growth through interaction with rotundifolia3/CYP90C1 in Arabidopsis
J. Exp. Bot.
64
613-624
2013
Arabidopsis thaliana
brenda
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1.14.14.147 3-epi-6-deoxocathasterone 23-monooxygenase
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