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Information on EC 4.1.1.102 - phenacrylate decarboxylase
for references in articles please use BRENDA:EC4.1.1.102
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IUBMB Comments
The enzyme, found in fungi, catalyses the decarboxylation of phenacrylic acids present in plant cell walls. It requires a prenylated flavin cofactor that is produced by EC 2.5.1.129, flavin prenyltransferase.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 4.1.1.102
-
p-coumaric
- styrene
- 4-vinylguaiacol
- decarboxylases
- 4-vinylphenol
-
4-vinyl
-
prfmn
-
phenylacrylic
-
1,3-dipolar
- synthesis
- pentosaceus
- 4-ethylphenol
-
vanillyl
- degradation
- brewing
Reaction Schemes
showSynonyms
phenolic acid decarboxylase, ferulic acid decarboxylase, fadase, phenacrylate decarboxylase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FADase
FDC1
ferulic acid decarboxylase
-
-
-
-
PAD
PAD1
phenolic acid decarboxylase
FDC1
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-coumarate = 4-vinylphenol + CO2
(1)
-
-
-
ferulate = 4-vinylguaiacol + CO2
(3)
-
-
-
trans-cinnamate = styrene + CO2
(2)
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
3-phenylprop-2-enoate carboxy-lyase
The enzyme, found in fungi, catalyses the decarboxylation of phenacrylic acids present in plant cell walls. It requires a prenylated flavin cofactor that is produced by EC 2.5.1.129, flavin prenyltransferase.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-methoxycinnamic acid
3-methoxystyrene + CO2
Substrates: -
Products: -
Products: -
?
3-nitrocinnamic acid
3-nitrostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-aminocinnamic acid
4-aminostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-bromocinnamic acid
4-bromostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-chlorocinnamic acid
4-chlorostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-cyanocinnamic acid
4-cyanostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-fluorocinnamic acid
4-fluorostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-formylcinnamic acid
4-formylstyrene + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamic acid
4-hydroxystyrene + CO2
Substrates: -
Products: -
Products: -
?
4-methoxycinnamic acid
4-methoxystyrene + CO2
Substrates: -
Products: -
Products: -
?
4-methylcinnamic acid
4-methylstyrene + CO2
Substrates: -
Products: -
Products: -
?
4-nitrocinnamic acid
4-nitrostyrene + CO2
Substrates: -
Products: -
Products: -
?
4-coumarate
4-vinylphenol + CO2
Substrates: 104% of the activity with ferulate
Products: -
Products: -
?
4-coumarate
4-vinylphenol + CO2
Substrates: -
Products: -
Products: -
?
4-coumarate
4-vinylphenol + CO2
Substrates: 104% of the activity with ferulate
Products: -
Products: -
?
4-coumarate
4-vinylphenol + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamate
4-hydroxystyrene + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamate
4-hydroxystyrene + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamate
4-hydroxystyrene + CO2
Substrates: 66% of the rate with ferulate
Products: -
Products: -
?
4-hydroxycinnamic acid
4-vinylphenol + CO2
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamic acid
4-vinylphenol + CO2
-
Substrates: -
Products: -
Products: -
?
4-hydroxycinnamic acid
4-vinylphenol + CO2
Substrates: -
Products: -
Products: -
?
caffeate
3,4-dihydroxystyrene + CO2
Substrates: -
Products: 14% of the activity with ferulate
Products: 14% of the activity with ferulate
?
caffeate
3,4-dihydroxystyrene + CO2
Substrates: -
Products: 14% of the activity with ferulate
Products: 14% of the activity with ferulate
?
ferulate
4-vinylguaiacol + CO2
Substrates: -
Products: -
Products: -
?
ferulate
4-vinylguaiacol + CO2
Substrates: -
Products: -
Products: -
?
ferulate
4-vinylguaiacol + CO2
Substrates: -
Products: -
Products: -
?
ferulate
4-vinylguaiacol + CO2
Substrates: -
Products: -
Products: -
?
trans-cinnamate
styrene + CO2
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: no substrates: 2- or 3-hydroxycinnamate
Products: -
Products: -
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additional information
?
-
-
Substrates: no substrates: 2- or 3-hydroxycinnamate
Products: -
Products: -
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additional information
?
-
Substrates: CO2 release must occur after protonation of the product. For a range of para- and meta-substituted phenylacrylic acids, the log(kcat/KM) value for the reaction correlates well with the Hammett delta- parameter with rho = 0.39 and r2 = 0.93 consistent with the rate-determining step being the formation of styrene from the prenylated flavin-product adduct through a cycloelimination reaction
Products: -
Products: -
?
additional information
?
-
-
Substrates: CO2 release must occur after protonation of the product. For a range of para- and meta-substituted phenylacrylic acids, the log(kcat/KM) value for the reaction correlates well with the Hammett delta- parameter with rho = 0.39 and r2 = 0.93 consistent with the rate-determining step being the formation of styrene from the prenylated flavin-product adduct through a cycloelimination reaction
Products: -
Products: -
?
additional information
?
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Substrates: proposed mechanism involves the formation of a putative pentacyclic intermediate formed by a 1,3 dipolar cyclo-addition of cofactor prenylated FMN with the alpha-beta double bond of the substrate, which serves to activate the substrate toward decarboxylation. Prenylated FMN is able to function as a dipole in a 1,3 dipolar cyclo-addition reaction as the initial step
Products: -
Products: -
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-coumarate
4-vinylphenol + CO2
Substrates: -
Products: -
Products: -
?
ferulate
4-vinylguaiacol + CO2
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(Z)-2-fluoro-2-nitro-vinylbenzene
potent irreversible inhibitor. At 0.05 mM, enzyme is inactive within 10 min
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
dithiothreitol
0.2-1 mM, slightly enhances decarboxylation of ferulic acid without affecteing decarboxylation of 4-coumarate
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Tuberculosis
Structural and functional characterization of the transcriptional regulator Rv3488 of Mycobacterium tuberculosis H37Rv.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 6
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4 - 7
5 - 7
-
pH 5.0-6.0: maximal activity, pH 7.0: about 45% of maximal activity
4 - 7
pH 4.0: about 30% of maximal activity, pH 7.0: about 60% of maximal activity
4 - 7
pH 4.0: maximal activity, pH 7.0: about 65% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
10 - 30
-
10Ā°C: about 39% of maximal activity, 30Ā°C: maximal activity, 40Ā°C: no activity
10 - 50
10Ā°C: about 70% of maximal activity, 50Ā°C: about 40% of maximal activity
20 - 50
20Ā°C: about 70% of maximal activity, 50Ā°C: about 30% of maximal activity
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
an endogenous amino thiol-like compound with a molecular weight greater than 1400 Da activates
physiological function
-
gene expression in Streptomyces lividans leads to expression of FDC1 and conversion of trans-cinnamic acid to styrene
physiological function
protein PAD1 catalyzes the formation of a diffusible cofactor required by FDC for decarboxylase activity. Escherichia coli protein UbiX can also activate FDC
physiological function
-
an endogenous amino thiol-like compound with a molecular weight greater than 1400 Da activates
-
physiological function
-
gene expression in Streptomyces lividans leads to expression of FDC1 and conversion of trans-cinnamic acid to styrene
-
Show AA Sequence and Transmembrane Helices (738 entries)
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PDB
SCOP
CATH
UNIPROT
ORGANISM