Information on EC 1.14.13.11 - trans-cinnamate 4-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.11
-
RECOMMENDED NAME
GeneOntology No.
trans-cinnamate 4-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-cinnamate + NADPH + H+ + O2 = 4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
phenylpropanoid biosynthesis, initial reactions
-
-
suberin monomers biosynthesis
-
-
phenylpropanoid biosynthesis
-
-
Ubiquinone and other terpenoid-quinone biosynthesis
-
-
Phenylalanine metabolism
-
-
Phenylpropanoid biosynthesis
-
-
Flavonoid biosynthesis
-
-
Stilbenoid, diarylheptanoid and gingerol biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
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SYSTEMATIC NAME
IUBMB Comments
trans-cinnamate,NADPH:oxygen oxidoreductase (4-hydroxylating)
NADH also acts, more slowly. Involves a heme-thiolate protein (P-450).
CAS REGISTRY NUMBER
COMMENTARY hide
9077-75-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
cultivar Yuyi, Keenoo-Pama, and Huay-Siiton
-
-
Manually annotated by BRENDA team
L. cv. Galia
Uniprot
Manually annotated by BRENDA team
Eucalyptus urophylla Eucalyptus grandis
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
0A1Z2R7G7, A0A1Z2R7G9
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Petroselinum sp.
cv. Goldrich
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
Sorghum sp.
Sorghum-Sudangrass hybrid
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E)-3-(2,3-dimethoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2,3-dimethoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-chlorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-chloro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-ethoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-ethoxy-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-fluorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-fluoro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-methoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-methylphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-methylphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-nitrophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-nitrophenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-chlorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3-chloro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-fluorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3-fluoro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-methoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-methylphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-methylphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-nitrophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-nitrophenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-chlorocinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-fluorocinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
3-hydroxycinnamate + NADPH + H+ + O2
caffeate + NADP+ + H2O
show the reaction diagram
3-hydroxycinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
7-ethoxycoumarin + O2 + NADPH
umbelliferone + ?
show the reaction diagram
-
demethylase
-
-
?
7-methoxycoumarin + O2 + NADPH
umbelliferone + ?
show the reaction diagram
-
demethylase
-
-
?
chlorotoluron + O2 + NADPH
?
show the reaction diagram
-
methylhydroxylase activity
-
-
-
p-chloro-N-methylaniline + O2 + NADPH
p-chloroaniline + ?
show the reaction diagram
-
N-demethylase activity
-
-
?
trans-cinnamate + NADH + H+ + O2
4-hydroxycinnamate + NAD+ + H2O
show the reaction diagram
-
reaction with NADH shows 50% of the activity with NADPH
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamic acid + NADPH
?
show the reaction diagram
-
assay at 37C, pH 7.5, reaction stopped with HCl
-
-
?
additional information
?
-
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
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KCN
-
1 mM, increase to 125% of the activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,4-Naphthoquinone
Sorghum sp.
-
-
1-aminobenzotriazole
11-dodecynoic acid
-
slight
2,4-dichloro-1-prop-2-ynyloxy-benzene
-
-
2,4-dinitrophenol
-
0.1 mM, 83% loss of activity
2-isopropyl-4-pentenamide
-
-
2-mercaptoethanol
-
2.0 mM
3-(2,4-dichlorophenoxy)-1-propyne
-
mechanism-based inhibitor
3-phenoxy-1-propyne
-
mechanism-based inhibitor
4-amino-5-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.005 mM
4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.0039 mM
4-amino-5-(3-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.036 mM
4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(4-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-furan-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.00032 mM
4-amino-5-pyridin-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
4-amino-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.051 mM
4-amino-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.013 mM
4-amino-5-thiophen-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
8-methoxypsoralen
antimycin A
-
0.005 mM, 16% loss of activity
ascorbic acid
-
2.0 mM
benzoquinone
Sorghum sp.
-
-
chlorogenic acid
-
0.1 mM, 9% loss of activity
cis-cinnamate
Petroselinum sp.
-
competitive
CuSO4
-
1 mM, complete loss of activity
cytochrome c
-
hydroxylase activity with NADPH is strongly inhibited, activity with NADH is less susceptible
dithiothreitol
-
2.0 mM
EDTA
-
1 mM, 18% loss of activity
FAD
-
1 mM, 73% loss of activity
FMN
-
1 mM, 75% loss of activity
gallic acid
-
0.1 mM, 20% loss of activity
KCl
-
200 mM, 39% loss of activity. 500 mM, 69% loss of activity
KCN
-
10 mM, 21% loss of activity
menadione
MnCl2
-
1 mM, 27% loss of activity
NADP+
-
competitive
phenoxy-1-propyne
-
-
psoralen
Sodium azide
-
10 mM, 64% loss of activity
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
0.1 mM, stimulates
ascorbic acid
-
0.1 mM, stimulates
dithiothreitol
-
0.1 mM, stimulates
glutathione
-
0.1 mM, stimulates
Lipid
Petroselinum sp.
-
lipid component required
S-methyl 1,2,3-benzothiadiazole-7-carbothioate
-
treatment of fruits
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0131
(2E)-3-(2-ethoxyphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-methylphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-nitrophenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0022
2-chlorocinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0023
2-fluorocinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.01191 - 0.2949
3-hydroxycinnamate
-
0.0131
3-hydroxycinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.555
7-ethoxycoumarin
-
-
4
7-methoxycoumarin
-
-
0.013 - 0.06
NADPH
0.021
O2
Sorghum sp.
-
-
1.919
p-chloro-N-methylaniline
-
-
0.0005 - 1
trans-cinnamate
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0567
7-ethoxycoumarin
-
-
0.19
7-methoxycoumarin
-
-
0.000233
chlorotoluron
-
-
2.37
p-chloro-N-methylaniline
-
-
1.72 - 161.8
trans-cinnamate
additional information
additional information
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0048 - 0.0326
8-methoxypsoralen
0.34
cis-cinnamate
Petroselinum sp.
-
-
0.0054 - 0.00812
psoralen
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
4-amino-5-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.005
4-amino-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.005 mM
0.0039
4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.0039 mM
0.036
4-amino-5-(3-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.036 mM
0.1
4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.1
4-amino-5-(4-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.1
4-amino-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.1
4-amino-5-furan-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.00032
4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.00032 mM
0.045
4-amino-5-pyridin-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.045 mM
0.051
4-amino-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.051 mM
0.013
4-amino-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.013 mM
0.045
4-amino-5-thiophen-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.045 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8.8
-
about 50% of maximal activity at pH 5.5 and at pH 8.8
6.3 - 8.2
-
50% of maximal activity at pH 6.3 and pH 8.2
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 40
-
0C: 45% of maximal activity, 40C: 60% of maximal activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.61
calculated from sequence
8.74
0A1Z2R7G7, A0A1Z2R7G9
calculated from sequence
9.22
-
calculated from sequence
9.48
0A1Z2R7G7, A0A1Z2R7G9
calculated from sequence
9.58
calculated from sequence
9.65
calculated from sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
BnC4H-1 and BvC4H-2 are co-dominantly expressed; BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
relatively low expression level compared to roots
Manually annotated by BRENDA team
-
activity increases during aging of disks from very low initial values
Manually annotated by BRENDA team
-
specific to
Manually annotated by BRENDA team
BnC4H-1 and BvC4H-2 are co-dominantly expressed; BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
BnC4H-1 is dominant over BnC4H-2; BnC4H-1 is dominant over BnC4H-2
Manually annotated by BRENDA team
BnC4H-1 and BvC4H-2 are co-dominantly expressed in young and middle-stage seed. In old seed, BnC4H-2 is dominant over BnC4H-1; BnC4H-1 and BvC4H-2 are co-dominantly expressed in young and middle-stage seed. In old seed, BnC4H-2 is dominant over BnC4H-1
Manually annotated by BRENDA team
additional information
-
lignifying tissue specific expression analysis, overview
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57290
0A1Z2R7G7, A0A1Z2R7G9
calculated from sequence
57730
x * 57730, calculated from sequence; x * 57730, calculated from sequence
57900
calculated from sequence
58000
-
x * 58000, SDS-PAGE
58150
calculated from sequence
58200
calculated from sequence
59600
0A1Z2R7G7, A0A1Z2R7G9
calculated from sequence
61050
calculated from sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
;
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C or 4C, 0.1 M phosphate buffer, homogenate loses 2/3 of its activity in 24 h
-
1C, during first 8 days decrease of enzyme activity, with prolonged stroage time increase of enzyme activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
analysis of sequence variants (single nucleotide polymorphism)
cinnamate 4-hydroxylase and cinnamate 4-hydroxylase fused to the FLAG epitope expressed in yeast. A chimeric cinnamate 4-hydroxylase/green fluorescent protein gene is engineered and stable expressed in Arabidopsis
-
expressed in Escherichia coli
-
expressed in Saccharomyces cerevisiae
-
expressed in Saccharomyces cerevisiae strain WAT11
-
expressed in Saccharomyces strain INVSC2(CPR)
-
expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR)
expression in hairy roots using Agrobacterium rhizogenes-mediated transformation system
-
expression in microsomes of yeast strain INVSc1
-
expression in Saccharomyces cerevisiae
expression vector and yeast strain WAT11
expression vector and yeast strain WAT11; expression vector and yeast strain WAT11
0A1Z2R7G7, A0A1Z2R7G9
gene C4H, DNA and amino acid sequence determination and analysis, expression analysis by quantitative real-time PCR after elicitor treatment
-
gene SbC4H, DNA and amino acid sequence determination and analysis, quantitative transcription analysis by RT-PCR, sequence comparisons and phylogenetic tree
generation of transgenic tobacco lines with altered activity levels of cinnamic acid 4-hydroxylase by sense or antisense expression of an alfalafa cDNA
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quantitative PCR C4H expression analysis in stone fruits and other lignifying tissues, and analysis of involved transcription factors, expression analysis, overview
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quantitative real-time PCR expression analysis, sequence comparison and phylogenic tree
successful expression requires removal of the intron, yeast does not process the intron at all
-
the binary vector, renamed pBE:100F/101R, containing the coding region of tomato CYP73A24 in the sense orientation under the control of the CaMV35s promoter and nos terminator is transformed into tomato lines Moneymaker, a wild type line, and Old Gold Crimson, a natural high pigment line
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transformation of Nicotiana tabacum with a truncated enzyme from Phaseolus vulgaris
-
translational fusion with P450 reductase in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after methyl jasmonate treatment
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expression increases during the secondary wall development period in cotton fibers; expression reaches its highest level during the elongation stage of fiber development
expression is induced in early time points after wounding, i.e. 3-6 h. Upon salinity stress, enzyme is highly expressed for the periods of 3-6 h after treatment
methyl jasmonate induces the enzyme highest at 0.3 mM after 12 h treatment
significantly upregulated in young leaves and roots and strongly induced when subjected to drought stress
the expression level of is enhanced after treatment with abiotic stress inducers, UV irradiation or salicylic acid in the thallus of Plagiochasma appendiculatum
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A306T
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naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
G99E
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naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
R249K
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naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
additional information
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C4H downregulation using RNAi, phenotype, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biofuel production
Eucalyptus urophylla Eucalyptus grandis
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lignocellulosic materials provide an attractive replacement for food-based crops used to produce ethanol. Understanding the interactions within the cell wall is vital to overcome the highly recalcitrant nature of biomass. One factor imparting plant cell wall recalcitrance is lignin, which can be manipulated by making changes in the lignin biosynthetic pathway. Eucalyptus trees with down-regulated cinnamate 4-hydroxylase (C4H) or p-coumaroyl quinate/shikimate 3'-hydroxylase (C3'H) expression display lowered overall lignin content. Lowering lignin content rather than altering sinapyl alcohol/coniferyl alcohol/4-coumaryl alcohol ratios is found to have the largest impact on reducing recalcitrance of the transgenic eucalyptus variants. The development of lower recalcitrance trees opens up the possibility of using alternative pretreatment strategies in biomass conversion processes that can reduce processing costs
pharmacology
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trans-cinnamate 4-monooxygenase plays a key role in the ability of phenylpropanoid metabolism to channel carbon to produce the 4-methoxybenzoyl group on the disaccharide moiety of OSW-1 (3beta,16beta,17alpha-trihydroxycholest-5-en-22-one 16-O-[O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl]-(1->3)-2-O-acetyl-alpha-L-arabinopyranoside]). OSW-1 is about 10-100 times more cytotoxic than clinically applied anticanceragents such as mitomycin C, adriamycin, cisplatin, camptothecin, and paclitaxel, but has a low toxicity towards normal cells. This potency, in combination with a unique mechanism of action and selectivity toward malignant tumor cells, gives OSW-1 and its analogues great potential as anticancer agents