The Enzyme Database

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EC 1.1.1.415     
Accepted name: noscapine synthase
Reaction: narcotine hemiacetal + NAD+ = noscapine + NADH + H+
For diagram of noscapine biosynthesis, click here
Glossary: noscapine = (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]isobenzofuran-1(3H)-one
narcotine hemiacetal = (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydroisobenzofuran-1-ol
Other name(s): NOS (gene name)
Systematic name: narcotine hemiacetal:NAD+ 1-oxidoreductase
Comments: The enzyme, characterized from the plant Papaver somniferum (opium poppy), catalyses the last step in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Chen, X. and Facchini, P.J. Short-chain dehydrogenase/reductase catalyzing the final step of noscapine biosynthesis is localized to laticifers in opium poppy. Plant J. 77 (2014) 173–184. [PMID: 24708518]
2.  Li, Y., Li, S., Thodey, K., Trenchard, I., Cravens, A. and Smolke, C.D. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc. Natl. Acad. Sci. USA 115 (2018) E3922–E3931. [PMID: 29610307]
[EC 1.1.1.415 created 2018]
 
 
EC 1.14.14.163     
Accepted name: (S)-1-hydroxy-N-methylcanadine 13-hydroxylase
Reaction: (S)-1-hydroxy-N-methylcanadine + [reduced NADPH—hemoprotein reductase] + O2 = (13S,14R)-1,13-dihydroxy-N-methylcanadine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of noscapine biosynthesis, click here
Other name(s): CYP82X2 (gene name)
Systematic name: (S)-1-hydroxy-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (13-hydroxylating)
Comments: The enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dang, T.T., Chen, X. and Facchini, P.J. Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nat. Chem. Biol. 11 (2015) 104–106. [PMID: 25485687]
2.  Li, Y. and Smolke, C.D. Engineering biosynthesis of the anticancer alkaloid noscapine in yeast. Nat. Commun. 7:12137 (2016). [PMID: 27378283]
3.  Li, Y., Li, S., Thodey, K., Trenchard, I., Cravens, A. and Smolke, C.D. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc. Natl. Acad. Sci. USA 115 (2018) E3922–E3931. [PMID: 29610307]
[EC 1.14.14.163 created 2018]
 
 
EC 1.14.14.166     
Accepted name: (S)-N-methylcanadine 1-hydroxylase
Reaction: (S)-N-methylcanadine + [reduced NADPH—hemoprotein reductase] + O2 = (S)-1-hydroxy-N-methylcanadine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of noscapine biosynthesis, click here
Other name(s): CYP82Y1 (gene name)
Systematic name: (S)-N-methylcanadine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (1-hydroxylating)
Comments: This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dang, T.T. and Facchini, P.J. CYP82Y1 is N-methylcanadine 1-hydroxylase, a key noscapine biosynthetic enzyme in opium poppy. J. Biol. Chem. 289 (2014) 2013–2026. [PMID: 24324259]
2.  Li, Y., Li, S., Thodey, K., Trenchard, I., Cravens, A. and Smolke, C.D. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc. Natl. Acad. Sci. USA 115 (2018) E3922–E3931. [PMID: 29610307]
[EC 1.14.14.166 created 2018]
 
 
EC 1.14.14.167     
Accepted name: (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase
Reaction: (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + [reduced NADPH—hemoprotein reductase] + O2 = (13S,14R)-13-O-acetyl-1,8-dihydroxy-N-methylcanadine + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of noscapine biosynthesis, click here
Other name(s): CYP82X1 (gene name)
Systematic name: (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine 8-hydroxylase,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
Comments: This cytochrome P-450 (heme-thiolate) enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dang, T.T., Chen, X. and Facchini, P.J. Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nat. Chem. Biol. 11 (2015) 104–106. [PMID: 25485687]
2.  Li, Y. and Smolke, C.D. Engineering biosynthesis of the anticancer alkaloid noscapine in yeast. Nat. Commun. 7:12137 (2016). [PMID: 27378283]
3.  Li, Y., Li, S., Thodey, K., Trenchard, I., Cravens, A. and Smolke, C.D. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc. Natl. Acad. Sci. USA 115 (2018) E3922–E3931. [PMID: 29610307]
[EC 1.14.14.167 created 2018]
 
 
EC 1.14.19.68     
Accepted name: (S)-canadine synthase
Reaction: (S)-tetrahydrocolumbamine + [reduced NADPH—hemoprotein reductase] + O2 = (S)-canadine + [oxidized NADPH—hemoprotein reductase] + 2 H2O
For diagram of canadine biosynthesis, click here
Other name(s): (S)-tetrahydroberberine synthase; (S)-tetrahydrocolumbamine oxidase (methylenedioxy-bridge-forming); CYP719A (gene name)
Systematic name: (S)-tetrahydrocolumbamine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme catalyses an oxidative reaction that does not incorporate oxygen into the product. Oxidation of the methoxyphenol group of the alkaloid tetrahydrocolumbamine results in the formation of the methylenedioxy bridge of canadine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 114308-22-4
References:
1.  Rueffer, M. and Zenk, M.H. Canadine synthase from Thalictrum tuberosum cell cultures catalyses the formation of the methylenedioxy bridge in berberine synthesis. Phytochemistry 36 (1994) 1219–1223.
2.  Ikezawa, N., Tanaka, M., Nagayoshi, M., Shinkyo, R., Sakaki, T., Inouye, K. and Sato, F. Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J. Biol. Chem. 278 (2003) 38557–38565. [PMID: 12732624]
3.  Dang, T.T. and Facchini, P.J. Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy. FEBS Lett. 588 (2014) 198–204. [PMID: 24316226]
[EC 1.14.19.68 created 1999 as EC 1.1.3.36, transferred 2002 to EC 1.14.21.5, transferred 2018 to EC 1.14.19.68]
 
 
EC 2.1.1.352     
Accepted name: 3-O-acetyl-4′-O-demethylpapaveroxine 4′-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 3-O-acetyl-4′-O-demethylpapaveroxine = S-adenosyl-L-homocysteine + 3-O-acetylpapaveroxine
Glossary: 3-O-acetyl-4′-O-demethylpapaveroxine = 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 = 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
Systematic name: S-adenosyl-L-methionine:3-O-acetyl-4′-O-demethylpapaveroxine 4′-O-methyltransferase
Comments: This activity is part of the noscapine biosynthesis pathway, as characterized in the plant Papaver somniferum (opium poppy). It is catalysed by heterodimeric complexes of the OMT2 gene product and the product of either OMT3 or 6OMT. OMT2 is the catalytic subunit in both complexes.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Li, Y. and Smolke, C.D. Engineering biosynthesis of the anticancer alkaloid noscapine in yeast. Nat. Commun. 7:12137 (2016). [PMID: 27378283]
2.  Park, M.R., Chen, X., Lang, D.E., Ng, K.KS. and Facchini, P.J. Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Plant J. 95 (2018) 252–267. [PMID: 29723437]
[EC 2.1.1.352 created 2018]
 
 
EC 2.3.1.285     
Accepted name: (13S,14R)-1,13-dihydroxy-N-methylcanadine 13-O-acetyltransferase
Reaction: acetyl-CoA + (13S,14R)-1,13-dihydroxy-N-methylcanadine = (13S,14R)-13-O-acetyl-1-hydroxy-N-methylcanadine + CoA
For diagram of noscapine biosynthesis, click here
Other name(s): AT1 (gene name)
Systematic name: acetyl-CoA:(13S,14R)-1,13-dihydroxy-N-methylcanadine O-acetyltransferase
Comments: The enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dang, T.T., Chen, X. and Facchini, P.J. Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nat. Chem. Biol. 11 (2015) 104–106. [PMID: 25485687]
2.  Li, Y., Li, S., Thodey, K., Trenchard, I., Cravens, A. and Smolke, C.D. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc. Natl. Acad. Sci. USA 115 (2018) E3922–E3931. [PMID: 29610307]
[EC 2.3.1.285 created 2019]
 
 
EC 3.1.1.105     
Accepted name: 3-O-acetylpapaveroxine carboxylesterase
Reaction: 3-O-acetylpapaveroxine + H2O = narcotine hemiacetal + acetate
Glossary: 3-O-acetylpapaveroxine = 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
narcotine hemiacetal = (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydroisobenzofuran-1-ol
Other name(s): CXE1 (gene name)
Systematic name: 3-O-acetylpapaveroxine acetatehydrolase
Comments: The enzyme, characterized from the plant Papaver somniferum (opium poppy), participates in the biosynthesis of the isoquinoline alkaloid noscapine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dang, T.T., Chen, X. and Facchini, P.J. Acetylation serves as a protective group in noscapine biosynthesis in opium poppy. Nat. Chem. Biol. 11 (2015) 104–106. [PMID: 25485687]
2.  Park, M.R., Chen, X., Lang, D.E., Ng, K.KS. and Facchini, P.J. Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Plant J. 95 (2018) 252–267. [PMID: 29723437]
[EC 3.1.1.105 created 2019]
 
 


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