KEGG ENZYME: 1.14.19.54

ENZYME: 1.14.19.54

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

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)

R03833

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

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