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 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 | 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 | UniProt | Comment | Textmining |
---|---|---|---|
Eschscholzia californica | - |
two full-length P450 cDNAs, CYP719A2 and CYP7193A, isolated | - |
Eschscholzia californica | - |
CYP719A2 and CYP719A3 | - |
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 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 | 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 | Comment | Organism |
---|---|---|
CYP719A2 | - |
Eschscholzia californica |
CYP719A3 | - |
Eschscholzia californica |
methylenedioxy bridge-forming enzyme | - |
Eschscholzia californica |
stylopine synthase | - |
Eschscholzia californica |