KEGG   ORTHOLOGY: K22089
Entry
K22089                      KO                                     
Symbol
STOX, DBOX
Name
tetrahydroprotoberberine oxidase [EC:1.3.3.8]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00945  Sanguinarine biosynthesis, (S)-reticuline => sanguinarine
Reaction
R02880  (S)-tetrahydroberberine:oxigen oxidoreductase
R03722  (S)-tetrahydrocolumbamine:oxigen oxidoreductase
R04703  dihydrosanguinarine:oxygen oxidoreductase
R08795  tetrahydropalmatine:oxygen oxidoreductase
R11748  (S)-tetrahydropapaverine:oxygen oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K22089  STOX, DBOX; tetrahydroprotoberberine oxidase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.3  Acting on the CH-CH group of donors
   1.3.3  With oxygen as acceptor
    1.3.3.8  tetrahydroberberine oxidase
     K22089  STOX, DBOX; tetrahydroprotoberberine oxidase
Other DBs
GO: 0050328
Genes
PSOM: 113274966 113303200
AG: ADY15026(STOX) AGL44334(DBOX)
Reference
PMID:23118227
  Authors
Hagel JM, Beaudoin GA, Fossati E, Ekins A, Martin VJ, Facchini PJ
  Title
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis.
  Journal
J Biol Chem 287:42972-83 (2012)
DOI:10.1074/jbc.M112.420414
  Sequence
[ag:AGL44334]
Reference
PMID:21327819
  Authors
Gesell A, Chavez ML, Kramell R, Piotrowski M, Macheroux P, Kutchan TM
  Title
Heterologous expression of two FAD-dependent oxidases with (S)-tetrahydroprotoberberine oxidase activity from Arge mone mexicana and Berberis wilsoniae in insect cells.
  Journal
Planta 233:1185-97 (2011)
DOI:10.1007/s00425-011-1357-4
  Sequence
[ag:ADY15026]
LinkDB

KEGG   ENZYME: 1.3.3.8
Entry
EC 1.3.3.8                  Enzyme                                 
Name
tetrahydroberberine oxidase;
(S)-THB oxidase
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With oxygen as acceptor
Sysname
(S)-tetrahydroberberine:oxygen oxidoreductase
Reaction(IUBMB)
(S)-tetrahydroberberine + 2 O2 = berberine + 2 H2O2 [RN:R02880]
Reaction(KEGG)
R02880;
(other) R03722 R04703 R08795 R11748
Substrate
(S)-tetrahydroberberine [CPD:C03329];
O2 [CPD:C00007]
Product
berberine [CPD:C00757];
H2O2 [CPD:C00027]
Comment
The enzyme from Berberis sp. is a flavoprotein; that from Coptis japonica is not. (R)-Tetrahydroberberines are not oxidized.
History
EC 1.3.3.8 created 1990 (EC 1.5.3.8 created 1989, incorporated 1992)
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22089  tetrahydroprotoberberine oxidase
Genes
PSOM: 113274966 113303200
Reference
1
  Authors
Amann M, Nagakura N, Zenk MH.
  Title
(S)-Tetrahydroprotoberberine oxidase the final enzyme in protoberberine biosynthesis.
  Journal
Tetrahedron Lett 25:953-954 (1984)
Reference
2
  Authors
Okada N, Shinmyo A, Okada H, Yamada Y.
  Title
Purification and characterization of (S)-tetrahydroberberine oxidase from cultured Coptis japonica cells.
  Journal
Phytochemistry 27:979-982 (1988)
Other DBs
ExplorEnz - The Enzyme Database: 1.3.3.8
IUBMB Enzyme Nomenclature: 1.3.3.8
ExPASy - ENZYME nomenclature database: 1.3.3.8
BRENDA, the Enzyme Database: 1.3.3.8
CAS: 114705-00-9
LinkDB

KEGG   REACTION: R11748
Entry
R11748                      Reaction                               
Name
(S)-tetrahydropapaverine:oxygen oxidoreductase
Definition
(S)-Tetrahydropapaverine + 2 Oxygen <=> Papaverine + 2 Hydrogen peroxide
Equation
C21631 + 2 C00007 <=> C06533 + 2 C00027
Enzyme
1.3.3.8
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.3  Acting on the CH-CH group of donors
   1.3.3  With oxygen as acceptor
    1.3.3.8
     R11748  (S)-Tetrahydropapaverine + 2 Oxygen <=> Papaverine + 2 Hydrogen peroxide
Orthology
K22089  tetrahydroprotoberberine oxidase [EC:1.3.3.8]
LinkDB

DBGET integrated database retrieval system