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Enzyme Nomenclature
Information on EC 1.14.13.104 - (+)-menthofuran synthase
Word Map on EC 1.14.13.104
- 1.14.13.104
- peppermint
-
+-menthofuran
-
mentha
- piperita
-
monoterpene
-
terpenoids
-
undesirable
- 1-deoxy-d-xylulose-5-phosphate
- menthone
-
cosuppression
-
reductoisomerase
- mint
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The expected taxonomic range for this enzyme is: Mentha
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EC NUMBER 
COMMENTARY 
1.14.13.104
-
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RECOMMENDED NAME
GeneOntology No.
(+)-menthofuran synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-pulegone + NADPH + H+ + O2 = (+)-menthofuran + NADP+ + H2O
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(+)-pulegone,NADPH:oxygen oxidoreductase (9-hydroxylating)
A heme-thiolate protein (P-450). The conversion of substrate into product involves the hydroxylation of the syn-methyl (C9), intramolecular cyclization to the hemiketal and dehydration to the furan [1]. This is the second cytochrome P-450-mediated step of monoterpene metabolism in peppermint, with the other step being catalysed by EC 1.14.13.47, (S)-limonene 3-monooxygenase [1].
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
regulation of pulegone metabolism involves menthofuran, the flux of (+)-pulegone through pulegone reductase correlates negatively with the essential oil content of menthofuran, such that menthofuran, and pulegone increase, or decrease, in concert, overview, although (+)-menthofuran does not inhibit (+)-pulegone reductase activity, stem feeding with menthofuran selectively decreases enzyme transcript levels in immature leaves, thereby accounting for decreased reductase activity and increased pulegone content, overview
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-
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(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
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hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
GC-MS product analysis
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
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-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
pathways for monoterpene biosynthesis in peppermint, overview
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-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
hydroxylation of the syn-methyl group of (+)-pulegone, spontaneous intramolecular cyclization to the hemiketal, and dehydration to the furan
-
-
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
regulation of pulegone metabolism involves menthofuran, the flux of (+)-pulegone through pulegone reductase correlates negatively with the essential oil content of menthofuran, such that menthofuran, and pulegone increase, or decrease, in concert, overview, although (+)-menthofuran does not inhibit (+)-pulegone reductase activity, stem feeding with menthofuran selectively decreases enzyme transcript levels in immature leaves, thereby accounting for decreased reductase activity and increased pulegone content, overview
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-
-
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
Q947B7
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-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
pathways for monoterpene biosynthesis in peppermint, overview
-
-
?
(+)-pulegone + NADPH + H+ + O2
(+)-menthofuran + NADP+ + H2O
-
the principal pathway for monoterpene biosynthesis in peppermint, overview
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determinationand analysis, functional expression in Saccharomyces cerevisiae strains WAT11U and WAT21U, which constitutively express two different isoforms of the Arabidposis thaliana NADPH-cytochrome P450 reductase, and in Escherichia coli strain JM109
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expression of a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter, in Mentha x piperita plants using Agrobacterium tumefaciens strain EHA105 transfection method
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gene mfs, expression under control of the CaMV 35S promoter in transformed peppermint plants
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
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expression of a homologous antisense version of the menthofuran synthase cDNA, both driven by the CaMV 35S promoter, in Mentha x piperita plants leads to altered essential oil composition very similar in composition to the DXR46 plant transformed with the sense version of the reductoisomerase, overview
additional information
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overexpression and cosuppression of mfs results in the respective increase or decrease in the production of menthofuran
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.104)
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