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Literature summary for 1.5.1.27 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
Search for more literature for 1.5.1.27

Cloned(Commentary)

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

Protein Variants

Protein Variants Comment Organism
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

Localization

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

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1,2-dehydroreticulinium + NADPH + H+ Papaver somniferum
-
 (R)-reticuline + NADP+
-
 r
1,2-dehydroreticulinium + NADPH + H+ Papaver rhoeas
-
 (R)-reticuline + NADP+
-
 r
1,2-dehydroreticulinium + NADPH + H+ Papaver somniferum
-
 (R)-reticuline + NADP+
-
 ir
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

Organism UniProt Comment Textmining
Papaver rhoeas
-
-
-
Papaver somniferum
-
-
-
Papaver somniferum P0DKI7
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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+
-
 ?
1,2-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+
-
 ?
1,2-dehydroreticulinium + NADPH + H+
-
 Papaver somniferum (R)-reticuline + NADP+
-
 r
1,2-dehydroreticulinium + NADPH + H+
-
 Papaver rhoeas (R)-reticuline + NADP+
-
 r
1,2-dehydroreticulinium + NADPH + H+
-
 Papaver somniferum (R)-reticuline + NADP+
-
 ir
1,2-dehydroreticulinium + NADPH + H+ no activity in the back reaction Papaver somniferum (R)-reticuline + NADP+
-
 ir
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
1,2-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
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 ?
-
 ?
additional information enzyme PsREPI also catalyzes the stereochemical inversion of (S)-N-methylcoclaurine Papaver somniferum ?
-
 ?

Synonyms

Synonyms Comment Organism
DRR
-
 Papaver somniferum
DRR
-
 Papaver rhoeas
PrDRR
-
 Papaver rhoeas
PsDRR1
-
 Papaver somniferum
PsREPI
-
 Papaver somniferum
reticuline epimerase for the bifunctional enzyme Papaver somniferum

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
NADP+
-
 Papaver somniferum
NADP+
-
 Papaver rhoeas
NADPH
-
 Papaver somniferum
NADPH
-
 Papaver rhoeas