Information on EC 1.14.13.102 - psoralen synthase

Word Map on EC 1.14.13.102
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.102
-
RECOMMENDED NAME
GeneOntology No.
psoralen synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-marmesin + NADPH + H+ + O2 = psoralen + NADP+ + acetone + 2 H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
linear furanocoumarin biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(+)-marmesin,NADPH:oxygen oxidoreductase
This microsomal cytochrome P-450-dependent enzyme is specific for (+)-marmesin, and to a much lesser extent 5-hydroxymarmesin, as substrate. Furanocoumarins protect plants from fungal invasion and herbivore attack. (+)-Columbianetin, the angular furanocoumarin analogue of the linear furanocoumarin (+)-marmesin, is not a substrate for the enzyme but it is a competitive inhibitor.
CAS REGISTRY NUMBER
COMMENTARY hide
106527-99-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + 2 H2O
show the reaction diagram
-
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
show the reaction diagram
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
show the reaction diagram
additional information
?
-
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
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + 2 H2O
show the reaction diagram
-
-
-
-
?
(+)-marmesin + NADPH + H+ + O2
psoralen + NADP+ + acetone + H2O
show the reaction diagram
5-hydroxymarmesin + NADPH + H+ + O2
bergaptol + acetone + NADP+ + H2O
show the reaction diagram
additional information
?
-
-
umbelliferone is a better precursor of psoralens than either demethylsuberosin or marmesin
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
the psoralen synthase is a cytochrome-P450-dependent monooxygenase
additional information
-
Mg2+ does not affect the enzyme activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-columbianetin
i.e. (+)-3,4,2',3'-D4-columbianetin, competitive inhibition, binds to the active site, analogy modeling and docking analysis, mechanism-based inactivation
Ancymidole
BAS 110
BAS 111
BAS 978
-
carbon monoxide
-
-
cytochrome c
-
72% inhibition at 0.5 nM
ketoconazole
NADP+
-
43% product inhibition at 1 mM
Tetcyclacis
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
-
NADH acts synergistically with NADPH, but cannot substitute for NADPH
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00054 - 0.0015
(+)-marmesin
0.019 - 0.054
5-hydroxymarmesin
0.052
NADPH
-
pH 7.0, 20°C, microsomes
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
340
(+)-marmesin
Ammi majus
Q6QNI4
pH 7.0, 27°C, recombinant enzyme in microsomes
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.49
sequence calculation
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55891
x * 55891, sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 55891, sequence calculation
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
95
-
short exposure leads to complete inactivation
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by preparation of microsomes
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli DH5alpha cells
-
expressed in yeast strain WAT 11
gene CYP71AJ1, DNA and amino acid sequence determination and analysis, phylogenetic analysis, functional expression of the wild-type enzyme in Escherichia coli and Saccharomyces cerevisiae strain WAT11 requiring swapping the N-terminal membrane anchor domain with that of CYP73A1, expression of the enzyme mutant in yeast cells
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
M120V
site-directed mutagenesis