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show all sequences of 1.14.19.64

Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica

Ikezawa, N.; Iwasa, K.; Sato, F.; FEBS J. 274, 1019-1035 (2007)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
CYP719A2 and CYP719A3, DNA and amino acid sequence determination and analysis, expression patterns, expression in Saccharomyces cerevisiae microsomes; two full-length P450 cDNAs, CYP719A2 and CYP7193A, expression in Saccharomyces cerevisiae
Eschscholzia californica
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00054
-
(S)-scoulerine
CYP719A3 variant, determined with HPLC
Eschscholzia californica
0.032
-
(R,S)-scoulerine
CYP719A2 variant, determined with HPLC
Eschscholzia californica
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
Eschscholzia californica
-
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
Eschscholzia californica
stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
additional information
Eschscholzia californica
the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
?
-
-
-
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Eschscholzia californica
-
CYP719A2 and CYP719A3; two full-length P450 cDNAs, CYP719A2 and CYP7193A, isolated
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
additional information
tissue expression patterns of CYP719A2 and CYP719A3, overview
Eschscholzia californica
-
root
specific expression of CYP719A3
Eschscholzia californica
-
seedling
-
Eschscholzia californica
-
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
0.43 pmol/min/pmol P450 for the CYP719A2 variant, (R,S)-scoulerine as substrate; CYP719A2 variant uses only (R,S)-cheilanthifoline as substrate to produce stylopine when incubating with a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates; CYP719A3 and CYP719A2 do not react with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline and magnoflorine to make corresponding products with a methylenedioxy bridge; CYP719A3 but not CYP719A2 variant converts (S)-tetrahydrocolumbamine to (S)-tetrahydroberberine; CYP719A3 converts a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates to stylopine and nandinine
Eschscholzia californica
0.0000045
-
CYP719A3 variant, (S)-scoulerine as substrate, microsomal protein used for determination
Eschscholzia californica
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
-
673579
Eschscholzia californica
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
both CYP719A2 and CYP719A3 have stylopine synthase activity to catalyze methylenedioxy bridge-formation from cheilanthifoline to stylopine, but not cheilanthifoline synthase activity to convert scoulerine to cheilanthifoline, overview
673579
Eschscholzia californica
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine
673579
Eschscholzia californica
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
-
673579
Eschscholzia californica
(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
CYP719A3
673579
Eschscholzia californica
?
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
CYP719A3
673579
Eschscholzia californica
?
-
-
-
?
additional information
the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
673579
Eschscholzia californica
?
-
-
-
-
additional information
CYP719A2 has high substrate affinity only toward (R,S)-cheilanthifoline, whereas CYP719A3 has high affinity toward the three similar substrates (R,S)-cheilanthifoline, (S)-scoulerine, and (S)-tetrahydrocolumbamine, both show no activity with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine, overview
673579
Eschscholzia californica
?
-
-
-
-
Cloned(Commentary) (protein specific)
Commentary
Organism
CYP719A2 and CYP719A3, DNA and amino acid sequence determination and analysis, expression patterns, expression in Saccharomyces cerevisiae microsomes; two full-length P450 cDNAs, CYP719A2 and CYP7193A, expression in Saccharomyces cerevisiae
Eschscholzia californica
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00054
-
(S)-scoulerine
CYP719A3 variant, determined with HPLC
Eschscholzia californica
0.032
-
(R,S)-scoulerine
CYP719A2 variant, determined with HPLC
Eschscholzia californica
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
Eschscholzia californica
-
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
Eschscholzia californica
stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
additional information
Eschscholzia californica
the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
?
-
-
-
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
additional information
tissue expression patterns of CYP719A2 and CYP719A3, overview
Eschscholzia californica
-
root
specific expression of CYP719A3
Eschscholzia californica
-
seedling
-
Eschscholzia californica
-
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
additional information
-
0.43 pmol/min/pmol P450 for the CYP719A2 variant, (R,S)-scoulerine as substrate; CYP719A2 variant uses only (R,S)-cheilanthifoline as substrate to produce stylopine when incubating with a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates; CYP719A3 and CYP719A2 do not react with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline and magnoflorine to make corresponding products with a methylenedioxy bridge; CYP719A3 but not CYP719A2 variant converts (S)-tetrahydrocolumbamine to (S)-tetrahydroberberine; CYP719A3 converts a mixture of 0.4 microM (R,S)-cheilanthifoline and 0.4 microM S-scoulerine as substrates to stylopine and nandinine
Eschscholzia californica
0.0000045
-
CYP719A3 variant, (S)-scoulerine as substrate, microsomal protein used for determination
Eschscholzia californica
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
-
673579
Eschscholzia californica
(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
both CYP719A2 and CYP719A3 have stylopine synthase activity to catalyze methylenedioxy bridge-formation from cheilanthifoline to stylopine, but not cheilanthifoline synthase activity to convert scoulerine to cheilanthifoline, overview
673579
Eschscholzia californica
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
stylopine biosynthesis involves the sequential formation of two methylenedioxy bridges, (S)-stylopine is an important intermediate in the biosynthesis of benzophenanthridine alkaloids, such as sanguinarine
673579
Eschscholzia californica
(S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
-
673579
Eschscholzia californica
(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
CYP719A3
673579
Eschscholzia californica
?
-
-
-
?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2
CYP719A3
673579
Eschscholzia californica
?
-
-
-
?
additional information
the methylenedioxy bridge-forming enzyme is involved in stylopine biosynthesis in Eschscholzia californica, biosynthetic pathway for a variety of isoquinoline alkaloids, overview
673579
Eschscholzia californica
?
-
-
-
-
additional information
CYP719A2 has high substrate affinity only toward (R,S)-cheilanthifoline, whereas CYP719A3 has high affinity toward the three similar substrates (R,S)-cheilanthifoline, (S)-scoulerine, and (S)-tetrahydrocolumbamine, both show no activity with columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine, overview
673579
Eschscholzia californica
?
-
-
-
-
Other publictions for EC 1.14.19.64
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)
746047
Yahyazadeh
-
Cloning and characterization ...
Chelidonium majus
Plant Cell Physiol.
58
1421-1430
2017
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1
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1
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1
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2
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3
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1
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1
1
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1
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2
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3
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1
1
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746447
Hori
Efficient microbial productio ...
Eschscholzia californica
Sci. Rep.
6
22201
2016
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2
1
-
-
-
-
-
-
-
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3
-
-
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2
1
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728446
Takemura
Molecular cloning and characte ...
Eschscholzia californica
Phytochemistry
91
100-108
2013
-
-
-
-
-
-
-
-
-
-
-
2
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4
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2
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2
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2
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711025
Diaz Chavez
Characterization of two methyl ...
Argemone mexicana
Arch. Biochem. Biophys.
507
186-193
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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4
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2
-
1
1
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1
1
1
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1
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1
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4
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2
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1
1
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1
1
1
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1
1
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673579
Ikezawa
Molecular cloning and characte ...
Eschscholzia californica
FEBS J.
274
1019-1035
2007
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1
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2
-
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3
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7
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3
2
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8
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1
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2
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3
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3
2
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8
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395597
Bauer
-
Two methylenedioxy bridge form ...
Eschscholzia californica
Phytochemistry
30
2953-2961
1991
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-
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1
1
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1
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1
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1
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1
2
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1
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2
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1
1
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3
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3
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1
1
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1
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1
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1
2
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1
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1
1
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