| EC |
1.1.1.247 |
| Accepted name: |
codeinone reductase (NADPH) |
| Reaction: |
codeine + NADP+ = codeinone + NADPH + H+ |
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For diagram of morphine biosynthesis, click here |
| Systematic name: |
codeine:NADP+ oxidoreductase |
| Comments: |
Catalyses the reversible reduction of codeinone to codeine, which is a direct precursor of morphine in the opium poppy plant, Papaver somniferum. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 153302-41-1 |
| References: |
| 1. |
Lenz, R. and Zenk, M.H. Stereoselective reduction of codeinone, the penultimate step during morphine biosynthesis in Papaver somniferum. Tetrahedron Lett. 36 (1995) 2449–2452. |
| 2. |
Lenz, R. and Zenk, M.H. Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures. Eur. J. Biochem. 233 (1995) 132–139. [DOI] [PMID: 7588736] |
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| [EC 1.1.1.247 created 1999, modified 2001] |
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| EC |
1.14.11.31 |
| Accepted name: |
thebaine 6-O-demethylase |
| Reaction: |
thebaine + 2-oxoglutarate + O2 = neopinone + formaldehyde + succinate + CO2 |
| Other name(s): |
T6ODM |
| Systematic name: |
thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating) |
| Comments: |
Requires Fe2+. Catalyses a step in morphine biosynthesis. The product neopinione spontaneously rearranges to the more stable codeinone. The enzyme also catalyses the 6-O-demethylation of oripavine to morphinone, with lower efficiency. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
| References: |
| 1. |
Hagel, J.M. and Facchini, P.J. Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. Nat. Chem. Biol. 6 (2010) 273–275. [DOI] [PMID: 20228795] |
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| [EC 1.14.11.31 created 2010] |
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| EC |
5.3.3.24 |
| Accepted name: |
neopinone isomerase |
| Reaction: |
neopinone = codeinone |
| Glossary: |
neopinone = 3-methoxy-17-methyl-8,14-didehydro-4,5α-epoxymorphinan-6-one
codeinone = 3-methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one |
| Other name(s): |
NISO (gene name) |
| Systematic name: |
neopinone Δ8-Δ7-isomerase |
| Comments: |
The enzyme, characterized from the opium poppy (Papaver somniferum), participates in the biosynthesis of morphine. It also catalyses the isomerization of neomorphinone and morphinone. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Dastmalchi, M., Chen, X., Hagel, J.M., Chang, L., Chen, R., Ramasamy, S., Yeaman, S. and Facchini, P.J. Neopinone isomerase is involved in codeine and morphine biosynthesis in opium poppy. Nat. Chem. Biol. 15 (2019) 384–390. [DOI] [PMID: 30886433] |
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| [EC 5.3.3.24 created 2022] |
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