Information on EC 1.14.13.213 - bursehernin 5'-monooxygenase

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The expected taxonomic range for this enzyme is: Sinopodophyllum hexandrum

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EC NUMBER
COMMENTARY hide
1.14.13.213
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RECOMMENDED NAME
GeneOntology No.
bursehernin 5'-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(-)-bursehernin + NADPH + H+ + O2 = (-)-5'-demethylyatein + NADP+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
yatein biosynthesis I
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SYSTEMATIC NAME
IUBMB Comments
(-)-bursehernin,NADPH:oxygen oxidoreductase (5'-hydroxylating)
This cytochrome P450 enzyme, characterized from the plant Sinopodophyllum hexandrum, is involved in the biosynthetic pathway of podophyllotoxin, a non-alkaloid toxin lignan whose derivatives are important anticancer drugs.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
or Sinopodophyllum hexandrum, gene Phex524 or CYP71CU1
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
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(-)-5'-demethoxyyatein + NADPH + H+ + O2
(-)-5'-demethylyatein + NADP+ + H2O
show the reaction diagram
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(-)-5'-demethoxyyatein + NADPH + H+ + O2
(-)-5'-demethylyatein + NADP+ + H2O
show the reaction diagram
A0A0N9HTU1
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene Phex524 or CYP71CU1, 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
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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.213)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)