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Information on EC 2.5.1.139 - umbelliferone 6-dimethylallyltransferase and Organism(s) Petroselinum crispum and UniProt Accession W0SKS3

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IUBMB Comments
The enzyme from parsley (Petroselinum crispum) is specific for umbelliferone and prenyl diphosphate. A minor product is osthenol, which is produced by transfer of the prenyl group to C-8 of umbelliferone.
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This record set is specific for:
Petroselinum crispum
UNIPROT: W0SKS3
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The taxonomic range for the selected organisms is: Petroselinum crispum
The enzyme appears in selected viruses and cellular organisms
Synonyms
PcPT, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PcPT
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:umbelliferone 6-dimethylallyltransferase
The enzyme from parsley (Petroselinum crispum) is specific for umbelliferone and prenyl diphosphate. A minor product is osthenol, which is produced by transfer of the prenyl group to C-8 of umbelliferone.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + umbelliferone
diphosphate + demethylsuberosin
show the reaction diagram
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-
-
?
dimethylallyl diphosphate + umbelliferone
diphosphate + osthenol
show the reaction diagram
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minor product besides demethylsuberosin, about 5% of the amount of demethylsuberosin
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?
additional information
?
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enzyme has strict substrate specificity towards umbelliferone and dimethylallyl diphosphate, and a strong preference for the C6 position of the prenylated product (demethylsuberosin), leading to linear furanocoumarins. The C8-prenylated derivative (osthenol) is also formed, but to a much lesser extent
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?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045 - 0.079
dimethylallyl diphosphate
0.021 - 0.025
umbelliferone
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
expression in the coumarin-producing plant Ruta graveolens shows increased consumption of endogenous umbelliferone. Expression of the prenyltransferase and a 4–coumaroyl CoA 2'–hydroxylase gene in Nicotiana benthamiana, which does not produce furanocoumarins, results in formation of demethylsuberosin
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
U6DT_PETCR
400
8
44221
Swiss-Prot
Chloroplast (Reliability: 4)
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression in various parsley tissues is increased by UV irradiation, with a concomitant increase in furanocoumarin production
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Karamat, F.; Olry, A.; Munakata, R.; Koeduka, T.; Sugiyama, A.; Paris, C.; Hehn, A.; Bourgaud, F.; Yazaki, K.
A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley
Plant J.
77
627-638
2014
Petroselinum crispum (W0SKS3)
Manually annotated by BRENDA team