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Literature summary extracted from

  • Farrow, S.C.; Hagel, J.M.; Beaudoin, G.A.; Burns, D.C.; Facchini, P.J.
    Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy (2015), Nat. Chem. Biol., 11, 728-732 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.5.1.27 gene PrDRR, genetic map, recombinant expression of His-tagged enzyme in Saccharomyces cerevisiae Papaver rhoeas
1.5.1.27 gene PsDRR1, genetic map, recombinant expression of His-tagged enzyme in Saccharomyces cerevisiae Papaver somniferum

Protein Variants

EC Number Protein Variants Comment Organism
1.5.1.27 additional information RNAi-mediated silencing of the COR gene family in opium poppy8, and the pTRV2-REPI-a construct targeted a corresponding region in the AKR domain of enzyme PsREPI. Relative REPI transcript abundance is significantly reduced in plants subjected to virus-induced gene silencing using all three constructs as compared to those transformed with empty vector, and the resulting alkaloid profiles are remarkably similar in both the latex and roots Papaver somniferum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.14.19.54 0.004
-
 (S)-reticuline pH 7.8, temperature not specified in the publication Papaver somniferum
1.14.19.54 0.004
-
 (S)-reticuline pH 7.8, temperature not specified in the publication Papaver rhoeas

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.5.1.27 microsome
-
 Papaver somniferum
-
-
1.5.1.27 microsome
-
 Papaver rhoeas
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ Papaver somniferum
-
 (R)-reticuline + NADP+
-
 r
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ Papaver rhoeas
-
 (R)-reticuline + NADP+
-
 r
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ Papaver somniferum
-
 (R)-reticuline + NADP+
-
 ir
1.5.1.27 additional information Papaver somniferum the bifunctional CYP82Y2 fusion enzyme termed reticuline epimerase (PsREPI) is a fusion between a cytochrome P450 (CYP) and an aldo-keto reductase (AKR) catalyzes the S-to-R epimerization of reticuline via 1,2-dehydroreticuline ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.5.1.27 Papaver rhoeas
-
-
-
1.5.1.27 Papaver somniferum
-
-
-
1.5.1.27 Papaver somniferum P0DKI7
-
-
1.14.19.54 Papaver rhoeas A0A0H4ILM3
-
-
1.14.19.54 Papaver somniferum A0A0H4J0K0
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.5.1.27 recombinant His-tagged enzyme from Saccharomyces cerevisiae by nickel affinity chromatography Papaver somniferum
1.5.1.27 recombinant His-tagged enzyme from Saccharomyces cerevisiae by nickel affinity chromatography Papaver rhoeas

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.1.27 1,2-dehydro-N-methylcoclaurine + NADPH + H+ PrDRR reduces 1,2-dehydro-N-methylcoclaurine to N-methylcoclaurine, although the low product yield precludes determination of the enantiomer Papaver rhoeas N-methylcoclaurine + NADP+
-
 ?
1.5.1.27 1,2-dehydro-N-methylcoclaurine + NADPH + H+ PsDRR1 reduces 1,2-dehydro-N-methylcoclaurine to N-methylcoclaurine, although the low product yield precludes determination of the enantiomer Papaver somniferum N-methylcoclaurine + NADP+
-
 ?
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+
-
 Papaver somniferum (R)-reticuline + NADP+
-
 r
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+
-
 Papaver rhoeas (R)-reticuline + NADP+
-
 r
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+
-
 Papaver somniferum (R)-reticuline + NADP+
-
 ir
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ no activity in the back reaction Papaver somniferum (R)-reticuline + NADP+
-
 ir
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ under conditions favoring oxidation, PrDRR converts (R)-reticuline, but not (S)-reticuline, to 1,2-dehydroreticuline Papaver rhoeas (R)-reticuline + NADP+
-
 r
1.5.1.27 1,2-dehydroreticulinium + NADPH + H+ under conditions favoring oxidation, PsDRR1 converts (R)-reticuline, but not (S)-reticuline, to 1,2-dehydroreticuline Papaver somniferum (R)-reticuline + NADP+
-
 r
1.5.1.27 additional information the bifunctional CYP82Y2 fusion enzyme termed reticuline epimerase (PsREPI) is a fusion between a cytochrome P450 (CYP) and an aldo-keto reductase (AKR) catalyzes the S-to-R epimerization of reticuline via 1,2-dehydroreticuline Papaver somniferum ?
-
 ?
1.5.1.27 additional information enzyme PsREPI also catalyzes the stereochemical inversion of (S)-N-methylcoclaurine Papaver somniferum ?
-
 ?
1.14.19.54 (S)-3'-hydroxy-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver somniferum ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 (S)-3'-hydroxy-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver rhoeas ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 (S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver somniferum ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 (S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
-
 Papaver rhoeas ? + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 (S)-reticuline + [reduced NADPH-hemoprotein reductase] + O2 best substrate Papaver somniferum 1,2-dehydroreticuline + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 (S)-reticuline + [reduced NADPH-hemoprotein reductase] + O2 best substrate Papaver rhoeas 1,2-dehydroreticuline + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
 ?
1.14.19.54 additional information corresponding alkaloids lacking an N-methyl group are not accepted as substrates, and 1-benzylisoquinolines with C7 or C3' O-linked methyl groups are not converted Papaver somniferum ?
-
 ?
1.14.19.54 additional information corresponding alkaloids lacking an N-methyl group are not accepted as substrates, and 1-benzylisoquinolines with C7 or C3' O-linked methyl groups are not converted Papaver rhoeas ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.5.1.27 DRR
-
 Papaver somniferum
1.5.1.27 DRR
-
 Papaver rhoeas
1.5.1.27 PrDRR
-
 Papaver rhoeas
1.5.1.27 PsDRR1
-
 Papaver somniferum
1.5.1.27 PsREPI
-
 Papaver somniferum
1.5.1.27 reticuline epimerase for the bifunctional enzyme Papaver somniferum
1.14.19.54 CYP82Y2
-
 Papaver somniferum
1.14.19.54 CYP82Y2
-
 Papaver rhoeas
1.14.19.54 DRS
-
 Papaver somniferum
1.14.19.54 DRS
-
 Papaver rhoeas

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.5.1.27 6 9 reduction of 1,2-dehydroreticuline, broad pH optimum Papaver somniferum
1.5.1.27 6 9 reduction of 1,2-dehydroreticuline, broad pH optimum Papaver rhoeas
1.5.1.27 8.8
-
 oxidation of (R)-reticuline Papaver somniferum
1.5.1.27 8.8
-
 oxidation of (R)-reticuline Papaver rhoeas
1.14.19.54 7.8
-
-
 Papaver somniferum
1.14.19.54 7.8
-
-
 Papaver rhoeas

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.1.27 NADP+
-
 Papaver somniferum
1.5.1.27 NADP+
-
 Papaver rhoeas
1.5.1.27 NADPH
-
 Papaver somniferum
1.5.1.27 NADPH
-
 Papaver rhoeas