Information on EC 2.3.1.140 - rosmarinate synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.140
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RECOMMENDED NAME
GeneOntology No.
rosmarinate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
caffeoyl-CoA + (R)-3-(3,4-dihydroxyphenyl)lactate = CoA + rosmarinate
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
rosmarinic acid biosynthesis II
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Tyrosine metabolism
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SYSTEMATIC NAME
IUBMB Comments
caffeoyl-CoA:(R)-3-(3,4-dihydroxyphenyl)lactate 2'-O-caffeoyl-transferase
Involved, with EC 1.1.1.237 (hydroxyphenylpyruvate reductase) in the biosynthesis of rosmarinic acid. Characterized from the plant Melissa officinalis L. (lemon balm).
CAS REGISTRY NUMBER
COMMENTARY hide
117590-80-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
slightly induced by yeast extract or methyl jasmonate
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Manually annotated by BRENDA team
RAS gene
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Manually annotated by BRENDA team
strain Benth
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
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the enzyme catalyzes a step in the rosmarinic acid biosynthesis, pathway overview
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-coumaroyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + 2-O-(4-coumaroyl)-3-(3,4-dihydroxyphenyl)lactate
show the reaction diagram
4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate
show the reaction diagram
4-coumaroyl-CoA + D-phenyllactate
CoA + (R)-2-O-(4-coumaroyl)-3-phenyllactate
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + D-tyrosine
CoA + N-(4-coumaroyl)-D-tyrosine
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + shikimate
CoA + 5-O-(4-coumaroyl)shikimate
show the reaction diagram
-
-
-
?
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + rosmarinate
show the reaction diagram
caffeoyl-CoA + 3-(3-methoxy-4-hydroxyphenyl)lactate
CoA + 2-O-caffeoyl-3-(3-methoxy-4-hydroxyphenyl)lactate
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-caffeoyl-3-(3,4-dihydroxyphenyl)lactate
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-caffeoyl-3-(4-hydroxyphenyl)lactate
show the reaction diagram
caffeoyl-CoA + D-phenyllactate
CoA + (R)-2-O-caffeoyl-3-phenyllactate
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + D-tyrosine
CoA + N-caffeoyl-D-tyrosine
show the reaction diagram
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-
-
-
?
cinnamoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + 2-O-cinnamoyl-3-(3,4-dihydroxyphenyl)lactate
show the reaction diagram
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-
-
-
?
cinnamoyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-cinnamoyl-3-(4-hydroxyphenyl)lactate
show the reaction diagram
cinnamoyl-CoA + D-phenyllactate
CoA + (R)-2-O-cinnamoyl-3-phenyllactate
show the reaction diagram
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-
-
-
?
feruloyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + 2-O-feruloyl-3-(3,4-dihydroxyphenyl)lactate
show the reaction diagram
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-
-
-
?
feruloyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-feruloyl-3-(4-hydroxyphenyl)lactate
show the reaction diagram
sinapoyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-sinapoyl-3-(4-hydroxyphenyl)lactate
show the reaction diagram
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-
-
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?
additional information
?
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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
4-coumaroyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + 2-O-(4-coumaroyl)-3-(3,4-dihydroxyphenyl)lactate
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactate
show the reaction diagram
-
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the precursor for rosmarinic acid synthesis via further hydroxylations, overview
-
?
caffeoyl-CoA + 3-(3,4-dihydroxyphenyl)lactate
CoA + rosmarinate
show the reaction diagram
caffeoyl-CoA + 3-(4-hydroxyphenyl)lactate
CoA + 2-O-caffeoyl-3-(4-hydroxyphenyl)lactate
show the reaction diagram
-
-
-
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?
additional information
?
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,4-Dihydroxyphenylpyruvate
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4-Coumaroyl-CoA
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severe substrate inhibition of 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate as acceptor and less with 3-(3,4-dihydroxyphenyl)lactate
4-hydroxymercuribenzoate
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complete inhibition at concentrations higher than 0.5 mM
4-hydroxyphenylpyruvate
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CoA
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non-competitive inhibitor
rosmarinic acid
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strong inhibitor, at concentration higher than 0.2 mM, non-competitive
S(-)-3,4-dihydroxyphenyllactate
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additional information
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cinnamic acids are not inhibitory
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
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at 0.5 mM, 50% activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.37
3,4-Dihydroxyphenyllactate
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0.035 - 1.3
3-(3,4-Dihydroxyphenyl)lactate
0.0169 - 1.425
3-(4-hydroxyphenyl)lactate
0.0013 - 0.083
4-Coumaroyl-CoA
0.17
4-hydroxyphenyllactate
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0.0021 - 0.0945
caffeoyl-CoA
0.0158 - 0.0529
cinnamoyl-CoA
0.31
CoA
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reverse reaction
0.49 - 17.82
D-phenyllactate
0.0191 - 0.0364
Feruloyl-CoA
0.015
rosmarinic acid
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reverse reaction
additional information
additional information
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kinetics, overview
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.7
CoA
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non-competitive inhibitor
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.044
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pH 7.0, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3
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recombinant enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8.5
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half-maximal activity at pH 6.5 and pH 8.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
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4-coumaroyl-CoA as substrate
45
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recombinant enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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RAS activity decreases through the cell cultivation period, it is highest after 3-4 days and completely declined after 11 days, overview. The RAS expression level declines also durring cell cultivation and is almost undetectable after 6-9 days, and absent after 10 days
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
47932
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x * 47932, calculated
50600
1 * 50600, about, LAAT1, sequence determination
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 47932, calculated
monomer
1 * 50600, about, LAAT1, sequence determination
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
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486321
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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5 h, no loss of activity
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
O2-sensitive, 10 mM DTT enhances enzyme activity 600%, 0.5 mM ascorbate enhances activity 200%
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486319, 486321
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-18°C, several weeks in desalted state
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4°C, purified recombinant GST-tagged AAT1, in 50 mM Tris-Cl, pH 8.0, and 10 mM reduced glutathione, 4 weeks, stable
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant GST-tagged AAT1 from Escherichia coli by cell disruption through freeze-thaw cycles, and glutathione affinity chromatography
recombinant His-tagged RAS from Escherichia coli strain BL21(DE3)pLysS by nickel affinity chromatography, dialysis, and cleavage of the tag by thrombin followed by His affinity chromatography to eliminate the tag
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AAT1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree of BAHD acyltransferases, expression of GST-tagged AAT1 in Escherichia coli strain Rosetta(DE3)pLysS
gene cbras, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression of His-tagged RAS in Escherichia coli strain BL21(DE3)pLysS
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RAS gene, intron-free and single-copy gene, DNA and amino acid sequence determination and analysis, heterologous expression of N-terminally His6-tagged RAS in Escherichia coli strain BL21(DE3)pLysS
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