BRENDA - Enzyme Database show
show all sequences of 1.14.14.126

Multifunctional oxidosqualene cyclases and cytochrome P450 involved in the biosynthesis of apple fruit triterpenic acids

Andre, C.; Legay, S.; Deleruelle, A.; Nieuwenhuizen, N.; Punter, M.; Brendolise, C.; Cooney, J.; Lateur, M.; Hausman, J.; Larondelle, Y.; Laing, W.; New Phytol. 211, 1279-1294 (2016)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
gene CYP716A175, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis, transient recombinant expression in Nicotiana benthamiana using the transformation method via Agrobacterium tumefaciens strain GV3101. The higher oxidizing efficiency of CYP716A175 for lupeol and beta-amyrin compared with germanicol preferentially drives the whole reaction chain to the production of betulinate and oleanolate rather than morolic acid. Transient expression in Saccharomyces cerevisiae shows the presence of the intermediate erythrodiol in addition to oleanolate, but not of oleanolic aldehyde. Sequential three-step oxidation reaction leading to oleanolate, low efficiency of CYP716A75 to oxidize erythrodiol in yeast
Malus domestica
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
ursolate + 3 NADP+ + 4 H2O
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
oleanolate + 3 NADP+ + 4 H2O
-
-
?
germanicol + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
morolate + 3 NADP+ + 4 H2O
-
-
?
lupeol + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
betulinate + 3 NADP+ + 4 H2O
-
-
?
additional information
Malus domestica
CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Malus domestica
EB148173
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
additional information
gene expression pattern analysis of CYP716A175 in 20 apple cultivars
Malus domestica
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
ursolate + 3 NADP+ + 4 H2O
-
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
oleanolate + 3 NADP+ + 4 H2O
-
-
-
?
germanicol + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
morolate + 3 NADP+ + 4 H2O
-
-
-
?
lupeol + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
betulinate + 3 NADP+ + 4 H2O
-
-
-
?
additional information
CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position
748772
Malus domestica
?
-
-
-
-
additional information
CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position. CYP716A175 has a similar oxidizing capacity for the triterpene scaffold alpha-amyrin, beta-amyrin, and lupeol but not for germanicol
748772
Malus domestica
?
-
-
-
-
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Malus domestica
Cloned(Commentary) (protein specific)
Commentary
Organism
gene CYP716A175, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis, transient recombinant expression in Nicotiana benthamiana using the transformation method via Agrobacterium tumefaciens strain GV3101. The higher oxidizing efficiency of CYP716A175 for lupeol and beta-amyrin compared with germanicol preferentially drives the whole reaction chain to the production of betulinate and oleanolate rather than morolic acid. Transient expression in Saccharomyces cerevisiae shows the presence of the intermediate erythrodiol in addition to oleanolate, but not of oleanolic aldehyde. Sequential three-step oxidation reaction leading to oleanolate, low efficiency of CYP716A75 to oxidize erythrodiol in yeast
Malus domestica
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Malus domestica
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
ursolate + 3 NADP+ + 4 H2O
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
oleanolate + 3 NADP+ + 4 H2O
-
-
?
germanicol + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
morolate + 3 NADP+ + 4 H2O
-
-
?
lupeol + 3 O2 + 3 NADPH + 3 H+
Malus domestica
overall reaction
betulinate + 3 NADP+ + 4 H2O
-
-
?
additional information
Malus domestica
CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position
?
-
-
-
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
additional information
gene expression pattern analysis of CYP716A175 in 20 apple cultivars
Malus domestica
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
alpha-amyrin + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
ursolate + 3 NADP+ + 4 H2O
-
-
-
?
beta-amyrin + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
oleanolate + 3 NADP+ + 4 H2O
-
-
-
?
germanicol + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
morolate + 3 NADP+ + 4 H2O
-
-
-
?
lupeol + 3 O2 + 3 NADPH + 3 H+
overall reaction
748772
Malus domestica
betulinate + 3 NADP+ + 4 H2O
-
-
-
?
additional information
CYP716A175 catalyses the C-28 oxidation of alpha-amyrin, beta-amyrin, lupeol and germanicol, producing ursolic acid, oleanolic acid, betulinic acid, and putatively morolic acid. CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position
748772
Malus domestica
?
-
-
-
-
additional information
CYP716A175 catalyses the three-step oxidation of triterpene backbones at the C-28 position. CYP716A175 has a similar oxidizing capacity for the triterpene scaffold alpha-amyrin, beta-amyrin, and lupeol but not for germanicol
748772
Malus domestica
?
-
-
-
-
General Information
General Information
Commentary
Organism
evolution
CYP716A175 is clearly grouped with the CYP716A subfamily. Expression patterns of triterpene-related genes in different apple cultivars, overview
Malus domestica
General Information (protein specific)
General Information
Commentary
Organism
evolution
CYP716A175 is clearly grouped with the CYP716A subfamily. Expression patterns of triterpene-related genes in different apple cultivars, overview
Malus domestica
Other publictions for EC 1.14.14.126
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
744248
Zhan
Cytochrome P450 CYP716A254 ca ...
Anemone flaccida
Biochem. Biophys. Res. Commun.
495
1271-1277
2018
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1
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2
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1
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3
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1
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1
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1
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2
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1
2
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2
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1
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1
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1
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1
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2
2
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745002
Yasumoto
Functional characterization o ...
Solanum lycopersicum
Front. Plant Sci.
8
21
2017
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1
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6
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2
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4
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6
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2
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6
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6
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6
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2
4
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745906
Misra
Two CYP716A subfamily cytochr ...
Ocimum basilicum
New Phytol.
214
706-720
2017
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1
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1
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4
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3
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5
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3
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1
3
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1
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4
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3
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5
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1
3
3
1
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-
746004
Jo
beta-Amyrin synthase (EsBAS) ...
Eleutherococcus senticosus
Phytochemistry
135
53-63
2017
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1
-
-
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1
1
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4
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7
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2
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7
1
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3
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1
3
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1
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4
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2
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7
1
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1
2
2
1
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746048
Tamura
Cytochrome P450 monooxygenase ...
Platycodon grandiflorus
Plant Cell Physiol.
58
874-884
2017
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1
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4
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4
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11
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1
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2
4
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4
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8
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11
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2
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2
3
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746049
Han
Transcriptomic analysis of Ka ...
Kalopanax septemlobus
Plant Cell Physiol.
59
319-330
2017
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1
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2
1
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1
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7
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1
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1
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3
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1
3
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1
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1
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1
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1
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2
2
-
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746060
Tamura
CYP716A179 functions as a tri ...
Glycyrrhiza uralensis, Glycyrrhiza uralensis 308-19
Plant Cell Rep.
36
437-445
2017
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1
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16
-
6
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6
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18
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2
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1
2
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16
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6
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18
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748772
Andre
Multifunctional oxidosqualene ...
Malus domestica
New Phytol.
211
1279-1294
2016
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1
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5
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2
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1
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6
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1
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1
1
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5
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1
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6
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1
1
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732623
Han
The involvement of beta-amyrin ...
Panax ginseng
Plant Cell Physiol.
54
2034-2046
2013
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1
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1
1
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5
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2
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2
1
1
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1
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1
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1
1
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2
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2
1
1
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1
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1
1
1
1
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-
732622
Fukushima
CYP716A subfamily members are ...
Medicago truncatula, Vitis vinifera
Plant Cell Physiol.
52
2050-2061
2011
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2
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7
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6
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4
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2
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19
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3
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7
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4
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19
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732627
Carelli
Medicago truncatula CYP716A12 ...
Medicago truncatula
Plant Cell
23
3070-3081
2011
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1
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1
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1
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5
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5
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2
1
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1
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1
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1
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5
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2
1
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1
1
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