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:

KM Value [mM]

KM Value Maximum [mM]

Substrate

Commentary

Organism

Structure

0.00054

-

(S)-scoulerine

microsomal protein, pH 7.6, 30°C

Eschscholzia californica

Natural Substrates

Organism

Commentary (Nat. Sub.)

Natural Products

Commentary (Nat. Pro.)

Organism (Nat. Pro.)

Reversibility

ID

(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

?

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate

-

?

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

?

additional information

Eschscholzia californica

no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine

?

-

-

-

Substrates

Commentary Substrates

Literature (Substrates)

Organism

Products

Commentary (Products)

Literature (Products)

Organism (Products)

Reversibility

Substrate Product ID

(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

-

673579

Eschscholzia californica

stylopine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

-

?

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2

-

673579

Eschscholzia californica

(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate

-

-

?

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2

-

673579

Eschscholzia californica

(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

-

?

additional information

no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine

673579

Eschscholzia californica

?

-

-

-

-

KM Value [mM]

KM Value Maximum [mM]

Substrate

Commentary

Organism

Structure

0.00054

-

(S)-scoulerine

microsomal protein, pH 7.6, 30°C

Eschscholzia californica

Natural Substrates

Organism

Commentary (Nat. Sub.)

Natural Products

Commentary (Nat. Pro.)

Organism (Nat. Pro.)

Reversibility

ID

(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(R,S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

?

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate

-

?

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2

Eschscholzia californica

-

(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

?

additional information

Eschscholzia californica

no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine

?

-

-

-

Substrates

Commentary Substrates

Literature (Substrates)

Organism

Products

Commentary (Products)

Literature (Products)

Organism (Products)

Reversibility

ID

(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

-

673579

Eschscholzia californica

stylopine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

-

?

(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2

-

673579

Eschscholzia californica

(S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O

enzyme does not catalyze the methylenedioxy bridge-formation in ring D of scoulerine but strictly recognizes ring A of the substrate

-

-

?

(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2

-

673579

Eschscholzia californica

(S)-tetrahydroberberine + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

-

?

additional information

no substrates: columbamine, (R,S)-reticuline, (R,S)-norreticuline, (S)-N-methylcoclaurine, (S)-coclaurine, (R,S)-6-O-methylnorlaudanosoline, and magnoflorine

673579

Eschscholzia californica

?

-

-

-

-

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

Synonyms

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)

673579

Ikezawa

Molecular cloning and characte ...

Eschscholzia californica

FEBS J.

274

1019-1035

2007

-

-

1

-

-

-

-

1

2

-

-

4

-

1

-

-

-

-

-

3

-

-

5

-

2

-

-

-

-

-

-

-

-

-

-

-

-

-

1

-

-

-

-

-

-

-

1

2

-

-

4

-

-

-

-

-

3

-

-

5

-

-

-

-

-

-

-

-

-

1

-

-

1

-

-