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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). [DOI] [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]

3.1.1.105

Accepted name:

3-O-acetylpapaveroxine carboxylesterase

Reaction:

3-O-acetylpapaveroxine + H₂O = narcotine hemiacetal + acetate

For diagram of noscapine biosynthesis, click here

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. [DOI] [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]