The Enzyme Database

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EC 1.14.19.51     
Accepted name: (S)-corytuberine synthase
Reaction: (S)-reticuline + [reduced NADPH—hemoprotein reductase] + O2 = (S)-corytuberine + [oxidized NADPH—hemoprotein reductase] + 2 H2O.
For diagram of corytuberine and magnoflorine biosynthesis, click here
Other name(s): CYP80G2
Systematic name: (S)-reticuline,NADPH:oxygen oxidoreductase (C-C phenol-coupling; (S)-corytuberine-forming)
Comments: A cytochrome P-450 (heme-thiolate) protein. The enzyme is involved in the biosynthesis of the quaternary benzylisoquinoline alkaloid magnoflorine in the plant Coptis japonica. It is specific for (S)-reticuline.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ikezawa, N., Iwasa, K. and Sato, F. Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells. J. Biol. Chem. 283 (2008) 8810–8821. [DOI] [PMID: 18230623]
[EC 1.14.19.51 created 2017]
 
 
EC 1.14.19.54     
Accepted name: 1,2-dehydroreticuline synthase
Reaction: (S)-reticuline + [reduced NADPH—hemoprotein reductase] + O2 = 1,2-dehydroreticuline + [oxidized NADPH—hemoprotein reductase] + 2 H2O
For diagram of thebaine biosynthesis, click here
Glossary: reticuline = 1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Other name(s): STORR; CYP82Y2 (gene name); DRS (gene name)
Systematic name: (S)-reticuline,[reduced NADPH—hemoprotein reductase]:oxygen 1,2-oxidoreductase
Comments: A P-450 (heme-thiolate) cytochrome. The enzyme from Papaver rhoeas (field poppy) is specific for (S)-reticuline and does not act on the (R)-form. The enzyme from Papaver somniferum (opium poppy), which is involved in the biosynthesis of morphine and related alkaloids, forms a fusion protein with EC 1.5.1.27, 1,2-dehydroreticulinium reductase (NADPH), which catalyses the reduction of 1,2-dehydroreticuline to (R)-reticuline, thus forming an epimerase system that converts (S)-reticuline to (R)-reticuline.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Hirata, K., Poeaknapo, C., Schmidt, J. and Zenk, M.H. 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway. Phytochemistry 65 (2004) 1039–1046. [DOI] [PMID: 15110683]
2.  Winzer, T., Kern, M., King, A.J., Larson, T.R., Teodor, R.I., Donninger, S.L., Li, Y., Dowle, A.A., Cartwright, J., Bates, R., Ashford, D., Thomas, J., Walker, C., Bowser, T.A. and Graham, I.A. Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein. Science 349 (2015) 309–312. [DOI] [PMID: 26113639]
3.  Farrow, S.C., Hagel, J.M., Beaudoin, G.A., Burns, D.C. and Facchini, P.J. Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy. Nat. Chem. Biol. 11 (2015) 728–732. [DOI] [PMID: 26147354]
[EC 1.14.19.54 created 2018]
 
 
EC 1.21.3.3     
Accepted name: reticuline oxidase
Reaction: (S)-reticuline + O2 = (S)-scoulerine + H2O2
For diagram of stylopine biosynthesis, click here
Other name(s): BBE; berberine bridge enzyme; berberine-bridge-forming enzyme; tetrahydroprotoberberine synthase
Systematic name: (S)-reticuline:oxygen oxidoreductase (methylene-bridge-forming)
Comments: Contains FAD. The enzyme from the plant Eschscholtzia californica binds the cofactor covalently [3]. Acts on (S)-reticuline and related compounds, converting the N-methyl group into the methylene bridge (’berberine bridge’) of (S)-tetrahydroprotoberberines. The product of the reaction, (S)-scoulerine, is a precursor of protopine, protoberberine and benzophenanthridine alkaloid biosynthesis in plants.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 152232-28-5
References:
1.  Steffens, P., Nagakura, N. and Zenk, M.H. The berberine bridge forming enzyme in tetrahydroprotoberberine biosynthesis. Tetrahedron Lett. 25 (1984) 951–952.
2.  Dittrich, H. and Kutchan, T.M. Molecular cloning, expression and induction of the berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack. Proc. Natl. Acad. Sci. USA 88 (1991) 9969–9973. [DOI] [PMID: 1946465]
3.  Kutchan, T.M. and Dittrich, H. Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in higher plants. J. Biol. Chem. 270 (1995) 24475–24481. [DOI] [PMID: 7592663]
[EC 1.21.3.3 created 1989 as EC 1.5.3.9, transferred 2002 to EC 1.21.3.3]
 
 
EC 2.1.1.116     
Accepted name: 3′-hydroxy-N-methyl-(S)-coclaurine 4′-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 3′-hydroxy-N-methyl-(S)-coclaurine = S-adenosyl-L-homocysteine + (S)-reticuline
For diagram of reticuline biosynthesis, click here
Systematic name: S-adenosyl-L-methionine:3′-hydroxy-N-methyl-(S)-coclaurine 4′-O-methyltransferase
Comments: Involved in isoquinoline alkaloid metabolism in plants. The enzyme has also been shown to catalyse the methylation of (RS)-laudanosoline, (S)-3′-hydroxycoclaurine and (RS)-7-O-methylnorlaudanosoline.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 132084-81-2
References:
1.  Frenzel, T., Zenk, M.H. S-Adenosyl-L-methionine: 3′-hydroxy-N-methyl-(S)-coclaurine 4′-O-methyltransferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway. Phytochemistry 29 (1990) 3505–3511. [DOI]
[EC 2.1.1.116 created 1999]
 
 
EC 2.1.1.291     
Accepted name: (R,S)-reticuline 7-O-methyltransferase
Reaction: (1) S-adenosyl-L-methionine + (S)-reticuline = S-adenosyl-L-homocysteine + (S)-laudanine
(2) S-adenosyl-L-methionine + (R)-reticuline = S-adenosyl-L-homocysteine + (R)-laudanine
For diagram of laudanine biosynthesis, click here
Glossary: (S)-reticuline = (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
(R)-reticuline = (1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
(S)-laudanine = 5-[((1S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol
(R)-laudanine = 5-[((1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol
Systematic name: S-adenosyl-L-methionine:(R,S)-reticuline 7-O-methyltransferase
Comments: The enzyme from the plant Papaver somniferum (opium poppy) methylates (S)- and (R)-reticuline with equal efficiency and is involved in the biosynthesis of tetrahydrobenzylisoquinoline alkaloids.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Ounaroon, A., Decker, G., Schmidt, J., Lottspeich, F. and Kutchan, T.M. (R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy. Plant J. 36 (2003) 808–819. [DOI] [PMID: 14675446]
2.  Weid, M., Ziegler, J. and Kutchan, T.M. The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum. Proc. Natl. Acad. Sci. USA 101 (2004) 13957–13962. [DOI] [PMID: 15353584]
[EC 2.1.1.291 created 2013]
 
 
EC 2.1.1.337     
Accepted name: reticuline N-methyltransferase
Reaction: (1) S-adenosyl-L-methionine + (S)-reticuline = S-adenosyl-L-homocysteine + (S)-tembetarine
(2) S-adenosyl-L-methionine + (S)-corytuberine = S-adenosyl-L-homocysteine + (S)-magnoflorine
For diagram of corytuberine and magnoflorine biosynthesis, click here and for diagram of tembetarine biosynthesis, click here
Glossary: (S)-reticuline = (1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
(S)-tembetarine = (1S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-ol
(S)-corytuberine = (6aS)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-1,11-diol
(S)-magnoflorine = (6aS)-1,11-dihydroxy-2,10-dimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolinium
Other name(s): RNMT
Systematic name: S-adenosyl-L-methionine:(S)-reticuline N-methyltransferase
Comments: The enzyme from opium poppy (Papaver somniferum) can also methylate (R)-reticuline, tetrahydropapaverine, (S)-glaucine and (S)-bulbocapnine. It is involved in the biosynthesis of the quaternary benzylisoquinoline alkaloid magnoflorine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Morris, J.S. and Facchini, P.J. Isolation and characterization of reticuline N-methyltransferase involved in biosynthesis of the aporphine alkaloid magnoflorine in opium poppy. J. Biol. Chem. 291 (2016) 23416–23427. [DOI] [PMID: 27634038]
[EC 2.1.1.337 created 2017]
 
 


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