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Information on EC 2.3.1.110 - tyramine N-feruloyltransferase
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EC Tree
2.3.1.110 tyramine N-feruloyltransferaseIUBMB Comments
Cinnamoyl-CoA, 4-coumaroyl-CoA and sinapoyl-CoA can also act as donors, and some aromatic amines can act as acceptors.
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Word Map
- 2.3.1.110
- amide
-
pepper
- potato
- octopamine
-
hydroxycinnamic
-
plant-specific
- noradrenaline
- l-tyrosine
- capsicum
- annuum
- dopamine
- serotonin
-
endosperm-specific
-
solanum
-
multigene
-
4.1.1.25
- syringae
- tuberosum
- tabacum
- elicitor
-
xanthi
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cell-suspension
- sinapoyl-coa
- l-phenylalanine
-
self-processing
-
prolamin
- foot-and-mouth
-
4-coumarate:coenzyme
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n-p-coumaroyl
-
caffeoyl
- nutrition
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
hydroxycinnamoyl-coa:tyramine n-(hydroxycinnamoyl)transferase, tyramine n-hydroxycinnamoyltransferase, tyramine-hydroxycinnamoyl transferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
feruloyl-CoA tyramine N-feruloyl-CoA transferase
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-
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HTH
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-
-
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hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase
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-
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synthase, feruloyltyramine
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-
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THT
tyramine feruloyltransferase
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-
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tyramine N-feruloyl-CoA transferase
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-
-
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tyramine N-hydroxycinnamoyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
feruloyl-CoA + tyramine = CoA + N-feruloyltyramine
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Acyl group transfer
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-
-
-
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SYSTEMATIC NAME
IUBMB Comments
feruloyl-CoA:tyramine N-(hydroxycinnamoyl)transferase
Cinnamoyl-CoA, 4-coumaroyl-CoA and sinapoyl-CoA can also act as donors, and some aromatic amines can act as acceptors.
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CAS REGISTRY NUMBER
COMMENTARY
128909-19-3
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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
4-coumaroyl-CoA + octopamine
CoA + N-(4-coumaroyl)octopamine
-
-
-
?
4-coumaroyl-CoA + phenethylamine
CoA + N-(4-coumaroyl)phenethylamine
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-
-
?
4-coumaroyl-CoA + tryptamine
CoA + N-(4-coumaroyl)tryptamine
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-
-
?
caffeoyl-CoA + tryptamine
CoA + N-caffeoyltryptamine
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tryptamine at 17% the rate of phenylethylamine
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-
?
feruloyl-4'-phosphopantetheine + tyramine
4'-phosphopantetheine + feruloyltyramine
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-
-
-
?
feruloyl-CoA + (4-hydroxyphenyl)propylamine
CoA + feruloyl-(4-hydroxyphenyl)propylamine
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-
-
-
?
feruloyl-CoA + 3'-methoxyoctopamine
CoA + feruloyl-3'-methoxyoctopamine
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-
-
?
feruloyl-CoA + 3-methoxytyramine
CoA + feruloyl-3-methoxytyramine
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-
-
-
?
feruloyl-CoA + beta-phenylethylamine
CoA + feruloyl-beta-phenylethylamine
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-
-
-
?
feruloyl-CoA + N-methyltyramine
CoA + N-feruloyl-N-methyltyramine
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-
-
-
?
4-coumaroyl-CoA + tyramine
CoA + N-(4-coumaroyl)tyramine
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tyramine at 19% the rate of phenylethylamine
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-
?
4-coumaroyl-CoA + tyramine
CoA + N-(4-coumaroyl)tyramine
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-
-
?
4-coumaroyl-CoA + tyramine
CoA + N-(4-coumaroyl)tyramine
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i.e. 4-hydroxycinnamoyltyramine
?
4-coumaroyl-CoA + tyramine
CoA + N-(4-coumaroyl)tyramine
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i.e. 4-hydroxycinnamoyltyramine
?
caffeoyl-CoA + serotonin
CoA + N-caffeoylserotonin
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serotonin at 22% the rate of phenylethylamine
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-
?
caffeoyl-CoA + tyramine
CoA + N-caffeoyltyramine
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caffeoyl-CoA at 89% the rate of 4-coumaroyl-CoA
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-
?
cinnamoyl-CoA + tyramine
CoA + cinnamoyltyramine
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cinnamoyl-CoA at 66% the rate of 4-coumaroyl-CoA
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-
?
feruloyl-CoA + dopamine
CoA + feruloyldopamine
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feruloyl-CoA at 20% the rate of 4-coumaroyl-CoA, dopamine at 27% the rate of phenylethylamine
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-
?
feruloyl-CoA + noradrenaline
CoA + feruloylnoradrenaline
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synonym: norepinephrine
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-
?
feruloyl-CoA + tyramine
CoA + feruloyltyramine
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mainly the trans-form is produced, only traces of the cis-form can be found
?
feruloyl-CoA + tyramine
CoA + feruloyltyramine
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low specificity for cinnamoyl-CoA derivates and hydroxyphenethylamines
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?
additional information
?
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wild-type enzyme shows no activity with serotonin, mutant enzyms F145Y and F145Y/Y147F show activity with serotonin
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-
?
additional information
?
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recombinant LaAAT1 exhibits a broad substrate tolerance accepting (hydroxy)cinnamoyl-CoAs as acyl donors and not only tyramine, tryptamine, phenylethylamine, and anthranilic acid but also shikimic acid and 4-hydroxyphenyllactic acid as acceptors, showing substrate promiscuity
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?
additional information
?
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substrate specificity of recombinant AAT1, overview. No or poor activity with anthranilic acid
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?
additional information
?
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enzyme has a wide specificity for phenylethylamines and cinnamoyl-CoA thioesters but differs in the affinity for the substrate, thus indicating different isoenzymes
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?
additional information
?
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enzyme has a wide specificity for phenylethylamines and cinnamoyl-CoA thioesters but differs in the affinity for the substrate, thus indicating different isoenzymes
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?
additional information
?
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enzyme exerts control over the flux of intermediates involved in hydroxycinnamic acid amide of tyramine under some conditions
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?
additional information
?
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tyraminehydroxycinnamoyl transferase is directly implicated in the formation of hydroxycinnamic acid amides
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-
?
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NATURAL SUBSTRATE
NATURAL 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
?
-
recombinant LaAAT1 exhibits a broad substrate tolerance accepting (hydroxy)cinnamoyl-CoAs as acyl donors and not only tyramine, tryptamine, phenylethylamine, and anthranilic acid but also shikimic acid and 4-hydroxyphenyllactic acid as acceptors, showing substrate promiscuity
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-
?
additional information
?
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enzyme exerts control over the flux of intermediates involved in hydroxycinnamic acid amide of tyramine under some conditions
-
-
?
additional information
?
-
tyraminehydroxycinnamoyl transferase is directly implicated in the formation of hydroxycinnamic acid amides
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2-hydroxyphenyl)amino sulfinyl acetic acid 1,1-dimethyl ester
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i.e. OH-PAS, rapid inhibition, feruloyl-CoA prevents partially
diethyldicarbonate
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90% loss of activity after 5 min at 0.5 mM, preincubation with feruloyl-CoA protects
L-tyrosine beta-naphthylamide
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competitive with respect to tyramine, reversible in the presence of high concentrations of tyramine
L-tyrosine beta-naphthylamide
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competitive with respect to tyramine, reversible in the presence of high concentrations of tyramine
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Foot-and-Mouth Disease
Endosperm-specific expression of tyramine N-hydroxycinnamoyltransferase and tyrosine decarboxylase from a single self-processing polypeptide produces high levels of tyramine derivatives in rice seeds
Foot-and-Mouth Disease
Endosperm-specific expression of tyramine N-hydroxycinnamoyltransferase and tyrosine decarboxylase from a single self-processing polypeptide produces high levels of tyramine derivatives in rice seeds.
Infections
Systemic Potato virus X infection induces defence gene expression and accumulation of ?-phenylethylamine-alkaloids in potato.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.057
4-coumaroyl-CoA
with tyramine, pH 7.5, 30°C, recombinant AAT1
0.157
4-coumaroyl-CoA
with tryptamine, pH 7.5, 30°C, recombinant AAT1
0.3
4-coumaroyl-CoA
with phenethylamine, pH 7.5, 30°C, recombinant AAT1
0.326
caffeoyl-CoA
with tyramine, pH 7.5, 30°C, recombinant AAT1
0.49
cinnamoyl-CoA
with tyramine, pH 7.5, 30°C, recombinant AAT1
0.192
feruloyl-CoA
with tyramine, pH 7.5, 30°C, recombinant AAT1
0.112
phenethylamine
with 4-coumaroyl-CoA, pH 7.5, 30°C, recombinant AAT1
0.005
tyramine
with caffeoyl-CoA, pH 7.5, 30°C, recombinant AAT1
0.018
tyramine
with cinnamoyl-CoA, pH 7.5, 30°C, recombinant AAT1
0.036
tyramine
with 4-coumaroyl-CoA, pH 7.5, 30°C, recombinant AAT1
0.045 - 0.07
tyramine
-
+ p-coumaroyl-CoA, depending on the enzyme fraction used
0.0588 - 0.071
tyramine
-
+ feruloyl-CoA, depending on the enzyme fraction used
0.243
tyramine
with feruloyl-CoA, pH 7.5, 30°C, recombinant AAT1
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE