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Literature summary extracted from

  • Li, Y.; Smolke, C.
    Engineering biosynthesis of the anticancer alkaloid noscapine in yeast (2016), Nat. Commun., 7, 12137 .
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.14.14.163 synthesis reconstitution of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates Papaver somniferum
1.14.14.167 drug development reconstitute of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates Papaver somniferum

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.163 expression in Saccharomyces cerevisiae. Reconstitution of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates Papaver somniferum
1.14.14.167 expression in Saccharomyces cerevisiae. Reconstitution of the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates Papaver somniferum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.163 (S)-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 Papaver somniferum the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine (13S,14R)-1,13-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.167 (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 Papaver somniferum the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
2.1.1.352 S-adenosyl-L-methionine + 3-O-acetyl-4'-O-demethylpapaveroxine Papaver somniferum this activity is part of the noscapine biosynthesis pathway S-adenosyl-L-homocysteine + 3-O-acetylpapaveroxine
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.163 Papaver somniferum I3PLR0
-
-
1.14.14.167 Papaver somniferum I3V6B7
-
-
2.1.1.352 Papaver somniferum I3PLQ6 I3PLQ6: 4'-O-desmethyl-3-O-acetylpapaveroxine O-methyltransferase subunit MT2, I3PLQ7: 4'-O-desmethyl-3-O-acetylpapaveroxine O-methyltransferase subunit MT3
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.163 (S)-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine Papaver somniferum (13S,14R)-1,13-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.163 (S)-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 the enzyme shows strict substrate specificity Papaver somniferum (13S,14R)-1,13-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.167 (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver somniferum (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
1.14.14.167 (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH-hemoprotein reductase] + O2 the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine Papaver somniferum (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH-hemoprotein reductase] + H2O
-
 ?
2.1.1.352 S-adenosyl-L-methionine + 3-O-acetyl-4'-O-demethylpapaveroxine this activity is part of the noscapine biosynthesis pathway Papaver somniferum S-adenosyl-L-homocysteine + 3-O-acetylpapaveroxine
-
 ?
2.1.1.352 S-adenosyl-L-methionine + 3-O-acetyl-4'-O-demethylpapaveroxine 3-O-acetyl-4'-O-demethylpapaveroxine i.e. 6-[(S)-acetoxy[(5R)-4-hydroxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]-2,3-dimethoxybenzaldehyde. 3-O-Acetylpapaveroxine i.e. 6-[(S)-acetoxy[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]-2,3-dimethoxybenzaldehyde Papaver somniferum S-adenosyl-L-homocysteine + 3-O-acetylpapaveroxine
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.163 CYP82X2
-
 Papaver somniferum
1.14.14.167 CYP82X1
-
 Papaver somniferum

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.167 cytochrome P-450 heme-thiolate enzyme Papaver somniferum

General Information

EC Number General Information Comment Organism
1.14.14.163 metabolism the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine Papaver somniferum
1.14.14.167 metabolism the enzyme participates in the biosynthesis of the isoquinoline alkaloid noscapine Papaver somniferum
2.1.1.352 metabolism this activity is part of the noscapine biosynthesis pathway Papaver somniferum