KEGG   ENZYME: 1.14.19.54Help
Entry
EC 1.14.19.54               Enzyme                                 

Name
1,2-dehydroreticuline synthase;
STORR;
CYP82Y2 (gene name);
DRS (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
BRITE hierarchy
Sysname
(S)-reticuline,[reduced NADPH---hemoprotein reductase]:oxygen 1,2-oxidoreductase
Reaction(IUBMB)
(S)-reticuline + [reduced NADPH---hemoprotein reductase] + O2 = 1,2-dehydroreticuline + [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R03833]
Reaction(KEGG)
Substrate
(S)-reticuline [CPD:C02105];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
1,2-dehydroreticuline [CPD:C06167];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
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.
History
EC 1.14.19.54 created 2018
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22093  1,2-dehydroreticuline synthase/reductase
Genes
PSOM: 113322712
Taxonomy
Reference
1  [PMID:15110683]
  Authors
Hirata K, Poeaknapo C, Schmidt J, Zenk MH
  Title
1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway.
  Journal
Phytochemistry 65:1039-46 (2004)
DOI:10.1016/j.phytochem.2004.02.015
Reference
2  [PMID:26113639]
  Authors
Winzer T, Kern M, King AJ, Larson TR, Teodor RI, Donninger SL, Li Y, Dowle AA, Cartwright J, Bates R, Ashford D, Thomas J, Walker C, Bowser TA, Graham IA
  Title
Plant science. Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein.
  Journal
Science 349:309-12 (2015)
DOI:10.1126/science.aab1852
Reference
3  [PMID:26147354]
  Authors
Farrow SC, Hagel JM, Beaudoin GA, Burns DC, Facchini PJ.
  Title
Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy.
  Journal
Nat Chem Biol 11:728-32 (2015)
DOI:10.1038/nchembio.1879
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.54
IUBMB Enzyme Nomenclature: 1.14.19.54
ExPASy - ENZYME nomenclature database: 1.14.19.54
BRENDA, the Enzyme Database: 1.14.19.54
LinkDB All DBs

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