Information on EC 1.14.13.214 - (-)-4'-demethyl-deoxypodophyllotoxin 4-hydroxylase

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The expected taxonomic range for this enzyme is: Sinopodophyllum hexandrum

EC NUMBER
COMMENTARY hide
1.14.13.214
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RECOMMENDED NAME
GeneOntology No.
(-)-4'-demethyl-deoxypodophyllotoxin 4-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(-)-4'-demethyldeoxypodophyllotoxin + NADPH + H+ + O2 = (-)-4'-demethylepipodophyllotoxin + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(-)-4'-desmethyl-epipodophyllotoxin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(-)-deoxypodophyllotoxin,NADPH:oxygen oxidoreductase (4-hydroxylating)
This cytochrome P450 enzyme, characterized from the plant Sinopodophyllum hexandrum, produces the direct precursor to etoposide, a potent anticancer drug. It can also act on (-)-deoxypodophyllotoxin with lower efficiency.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
or Sinopodophyllum hexandrum, gene CYP82D61
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
the enzyme is involved in the biosynthesis of (-)-4'-demethylepipodophyllotoxin (the etoposide aglycone), a naturally occurring lignan that is the immediate precursor of etoposide and, unlike podophyllotoxin, a potent topoisomerase inhibitor. Biosynthetic pathway of (-)-podophyllotoxin, overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(-)-4'-demethyl-deoxypodophyllotoxin + NADPH + H+ + O2
(-)-4'-demethylepipodophyllotoxin + NADP+ + H2O
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene CYP82D61, expression analysis by qRT-PCR analysis, transcriptome mining to identify biosynthetic genes in the podophyllotoxin pathway, Agrobacterium-mediated functional transient expression in Nicotiana benthamiana
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
recombinant coexpression of the genes involved in the podophyllotoxin pathway permits to reconstitute the pathway to (-)-4'-demethylepipodophyllotoxin (the etoposide aglycone), a naturally occurring lignan that is the immediate precursor of etoposide and, unlike podophyllotoxin, a potent topoisomerase inhibitor, for production of the etoposide aglycone in tobacco and circumvent the need for cultivation of mayapple and semisynthetic epimerization and demethylation of podophyllotoxin