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

for references in articles please use BRENDA:EC1.14.13.214
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The expected taxonomic range for this enzyme is: Sinopodophyllum hexandrum

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EC NUMBER
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1.14.13.214
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RECOMMENDED NAME
GeneOntology No.
(-)-4'-demethyl-deoxypodophyllotoxin 4-hydroxylase
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REACTION
REACTION DIAGRAM
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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 P-450 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.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
or Sinopodophyllum hexandrum, gene CYP82D61
UniProt
Manually annotated by BRENDA team
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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
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
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LITERATURE
(Substrate)
COMMENTARY
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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
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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
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APPLICATION
ORGANISM
UNIPROT
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.214)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)