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Literature summary for 1.14.19.64 extracted from

  • Ikezawa, N.; Iwasa, K.; Sato, F.
    Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica (2007), FEBS J., 274, 1019-1035.
    View publication on PubMed
Search for more literature for 1.14.19.64

Cloned(Commentary)

Cloned (Comment) Organism
CYP719A2 and CYP719A3, DNA and amino acid sequence determination and analysis, expression patterns, expression in Saccharomyces cerevisiae microsomes Eschscholzia californica
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 Comment 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 Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(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 UniProt Comment Textmining
Eschscholzia californica
-
 two full-length P450 cDNAs, CYP719A2 and CYP7193A, isolated
-
Eschscholzia californica
-
 CYP719A2 and CYP719A3
-

Source Tissue

Source Tissue Comment 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] Comment Organism
additional information
-
 0.43 pmol/min/pmol P450 for the CYP719A2 variant, (R,S)-scoulerine as substrate Eschscholzia californica
additional information
-
 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 Eschscholzia californica
additional information
-
 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 Eschscholzia californica
additional information
-
 CYP719A3 but not CYP719A2 variant converts (S)-tetrahydrocolumbamine to (S)-tetrahydroberberine Eschscholzia californica
additional information
-
 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 Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R,S)-cheilanthifoline + [reduced NADPH-hemoprotein reductase] + O2
-
 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 Eschscholzia californica (S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
(R,S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
-
 Eschscholzia californica (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 r
(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 Eschscholzia californica (S)-stylopine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2
-
 Eschscholzia californica (S)-nandinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
(S)-scoulerine + [reduced NADPH-hemoprotein reductase] + O2 CYP719A3 Eschscholzia californica ?
-
 ?
(S)-tetrahydrocolumbamine + [reduced NADPH-hemoprotein reductase] + O2 CYP719A3 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 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 Eschscholzia californica ?
-
 ?

Synonyms

Synonyms Comment Organism
CYP719A2
-
 Eschscholzia californica
CYP719A3
-
 Eschscholzia californica
methylenedioxy bridge-forming enzyme
-
 Eschscholzia californica
stylopine synthase
-
 Eschscholzia californica