KEGG ORTHOLOGY: K22093

ORTHOLOGY: K22093

Entry

K22093                      KO

Symbol

REPI

Name

1,2-dehydroreticuline synthase/reductase [EC:1.14.19.54 1.5.1.27]

Pathway

map00950

Isoquinoline alkaloid biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00944

Morphine biosynthesis, (S)-reticuline => morphine

Reaction

R03833

(S)-reticuline,[reduced NADPH---hemoprotein reductase]:oxygen 1,2-oxidoreductase

R04695

(R)-reticuline:NADP+ oxidoreductase

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22093  REPI; 1,2-dehydroreticuline synthase/reductase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.5  Acting on the CH-NH group of donors
   1.5.1  With NAD+ or NADP+ as acceptor
    1.5.1.27  1,2-dehydroreticulinium reductase (NADPH)
     K22093  REPI; 1,2-dehydroreticuline synthase/reductase
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.19  With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
    1.14.19.54  1,2-dehydroreticuline synthase
     K22093  REPI; 1,2-dehydroreticuline synthase/reductase

Genes

PSOM:

113322712

AG:	AKO60175(REPI)

Reference

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

[ag:AKO60175]

LinkDB

ENZYME: 1.5.1.27

Entry

EC 1.5.1.27                 Enzyme

Name

1,2-dehydroreticulinium reductase (NADPH);
1,2-dehydroreticulinium ion reductase

Class

Oxidoreductases;
Acting on the CH-NH group of donors;
With NAD+ or NADP+ as acceptor

Sysname

(R)-reticuline:NADP+ oxidoreductase

Reaction(IUBMB)

(R)-reticuline + NADP+ = 1,2-dehydroreticulinium + NADPH + H+ [RN:R04695]

Reaction(KEGG)

R04695

Substrate

(R)-reticuline [CPD:C05178];
NADP+ [CPD:C00006]

Product

1,2-dehydroreticulinium [CPD:C06167];
NADPH [CPD:C00005];
H+ [CPD:C00080]

Comment

Reduces the 1,2-dehydroreticulinium ion to (R)-reticuline, which is a direct precursor of morphinan alkaloids in the poppy plant. The enzyme does not catalyse the reverse reaction to any significant extent under physiological conditions.

History

EC 1.5.1.27 created 1999, modified 2004

Pathway

ec00950

Isoquinoline alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K22093

1,2-dehydroreticuline synthase/reductase

Genes

PSOM:

113322712

Reference

Authors

De-Eknamkul W, Zenk MH.

Title

Purification and properties of 1,2-dehydroreticulinium reductase from Papaver somniferum seedlings.

Journal

Phytochemistry 31:813-821 (1992)

Other DBs

ExplorEnz - The Enzyme Database:

1.5.1.27

IUBMB Enzyme Nomenclature:

1.5.1.27

ExPASy - ENZYME nomenclature database:

1.5.1.27

BRENDA, the Enzyme Database:

1.5.1.27

CAS:	130590-58-8

LinkDB

REACTION: R04695

Entry

R04695                      Reaction

Name

(R)-reticuline:NADP+ oxidoreductase

Definition

(R)-Reticuline + NADP+ <=> 1,2-Dehydroreticuline + NADPH

Equation

C05178 + C00006 <=> C06167 + C00005

Reaction class

RC00001

C00005_C00006

RC01200

C05178_C06167

Enzyme

1.5.1.27

Pathway

rn00950

Isoquinoline alkaloid biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00944

Morphine biosynthesis, (S)-reticuline => morphine

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  1.5  Acting on the CH-NH group of donors
   1.5.1  With NAD+ or NADP+ as acceptor
    1.5.1.27
     R04695  (R)-Reticuline + NADP+ <=> 1,2-Dehydroreticuline + NADPH

Orthology

K22093

1,2-dehydroreticuline synthase/reductase [EC:1.14.19.54 1.5.1.27]

Other DBs

RHEA:

17572

LinkDB

DBGET integrated database retrieval system