KEGG   ORTHOLOGY: K12692
Entry
K12692            Tight     KO                                     
Symbol
H6H
Name
hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase [EC:1.14.11.11 1.14.20.13]
Pathway
map00960  Tropane, piperidine and pyridine alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Reaction
R03737  (6S)-6beta-hydroxyhyoscyamine,2-oxoglutarate:oxygen oxidoreductase (epoxide-forming)
R03812  L-hyoscyamine,2-oxoglytarate:oxygen oxidoreductase ((6S)-hydroxylating)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00960 Tropane, piperidine and pyridine alkaloid biosynthesis
    K12692  H6H; hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.11  With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
    1.14.11.11  hyoscyamine (6S)-dioxygenase
     K12692  H6H; hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.13  6beta-hydroxyhyoscyamine epoxidase
     K12692  H6H; hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase
Other DBs
GO: 0047998 0047594
Genes
AG: BAA05630(H6H) BAA78340(H6H)
Reference
PMID:8066129
  Authors
Kanegae T, Kajiya H, Amano Y, Hashimoto T, Yamada Y
  Title
Species-dependent expression of the hyoscyamine 6 beta-hydroxylase gene in the pericycle.
  Journal
Plant Physiol 105:483-90 (1994)
DOI:10.1104/pp.105.2.483
  Sequence
Reference
PMID:8354403
  Authors
Hashimoto T, Matsuda J, Yamada Y
  Title
Two-step epoxidation of hyoscyamine to scopolamine is catalyzed by bifunctional hyoscyamine 6 beta-hydroxylase.
  Journal
FEBS Lett 329:35-9 (1993)
DOI:10.1016/0014-5793(93)80187-y
LinkDB

KEGG   ENZYME: 1.14.20.13
Entry
EC 1.14.20.13               Enzyme                                 
Name
6beta-hydroxyhyoscyamine epoxidase;
hydroxyhyoscyamine dioxygenase;
(6S)-6-hydroxyhyoscyamine,2-oxoglutarate oxidoreductase (epoxide-forming)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and the other dehydrogenated
Sysname
(6S)-6beta-hydroxyhyoscyamine,2-oxoglutarate:oxygen oxidoreductase (epoxide-forming)
Reaction(IUBMB)
(6S)-6beta-hydroxyhyoscyamine + 2-oxoglutarate + O2 = scopolamine + succinate + CO2 + H2O [RN:R03737]
Reaction(KEGG)
R03737
Substrate
(6S)-6beta-hydroxyhyoscyamine;
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
scopolamine [CPD:C01851];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001]
Comment
Requires Fe2+ and ascorbate.
History
EC 1.14.20.13 created 1992 as EC 1.14.11.14, transferred 2018 to EC 1.14.20.13
Pathway
ec00960  Tropane, piperidine and pyridine alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12692  hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase
Reference
1
  Authors
Hashimoto T, Kohno J, Yamada Y.
  Title
6beta-Hydroxyhyoscyamine epoxidase from cultured roots of Hyoscyamus niger.
  Journal
Phytochemistry 28:1077-1082 (1989)
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.13
IUBMB Enzyme Nomenclature: 1.14.20.13
ExPASy - ENZYME nomenclature database: 1.14.20.13
BRENDA, the Enzyme Database: 1.14.20.13
CAS: 121479-53-6
LinkDB

KEGG   REACTION: R03737
Entry
R03737                      Reaction                               
Name
(6S)-6beta-hydroxyhyoscyamine,2-oxoglutarate:oxygen oxidoreductase (epoxide-forming)
Definition
(6S)-Hydroxyhyoscyamine + 2-Oxoglutarate + Oxygen <=> Scopolamine + Succinate + CO2 + H2O
Equation
Reaction class
RC00989  C01851_C03325
Enzyme
Pathway
rn00960  Tropane, piperidine and pyridine alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.13
     R03737  (6S)-Hydroxyhyoscyamine + 2-Oxoglutarate + Oxygen <=> Scopolamine + Succinate + CO2 + H2O
Orthology
K12692  hyoscyamine (6S)-dioxygenase / 6beta-hydroxyhyoscyamine epoxidase [EC:1.14.11.11 1.14.20.13]
Other DBs
RHEA: 12800
LinkDB

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