Information on EC 3.1.1.35 - dihydrocoumarin hydrolase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.1.1.35
-
RECOMMENDED NAME
GeneOntology No.
dihydrocoumarin hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dihydrocoumarin + H2O = melilotate
show the reaction diagram
also hydrolyzes some other benzenoid 1,4-lactones
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-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
coumarin metabolism (to melilotic acid)
-
-
Polycyclic aromatic hydrocarbon degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
dihydrocoumarin lactonohydrolase
Also hydrolyses some other benzenoid 1,4-lactones.
CAS REGISTRY NUMBER
COMMENTARY hide
37278-47-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Buckl.
-
-
Manually annotated by BRENDA team
F101
-
-
Manually annotated by BRENDA team
F101
-
-
Manually annotated by BRENDA team
isolated as a 1-naphthol assimilating microorganism
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-
Manually annotated by BRENDA team
isolated as a 1-naphthol assimilating microorganism
-
-
Manually annotated by BRENDA team
L., alfalfa
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-
Manually annotated by BRENDA team
Desr., white sweet clover
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-
Manually annotated by BRENDA team
Lam., yellow sweet clover
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-
Manually annotated by BRENDA team
no activity in Hordeum vulgare
barley
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-
Manually annotated by BRENDA team
L., red clover
-
-
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
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + acetic acid + H2O2
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
show the reaction diagram
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
show the reaction diagram
2-coumaranone
?
show the reaction diagram
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
show the reaction diagram
3,4-dihydrocoumarin + H2O
?
show the reaction diagram
3,4-dihydrocoumarin + H2O
melilotate
show the reaction diagram
3H-benzofuran-2-one + H2O
2-hydroxyphenylacetic acid
show the reaction diagram
-
16% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
5-hydroxy-3H-benzofuran-2-one + H2O
homogentisic acid
show the reaction diagram
-
82% of the activity compared to 7-hydroxydihydrocoumarin
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-
?
6,7-dihydroxydihydrocoumarin + H2O
3-(2,3,6-trihydroxyphenyl)propionic acid
show the reaction diagram
7,8-dihydroxydihydrocoumarin + H2O
3-(3,4,6-trihydroxyphenyl)propionic acid
show the reaction diagram
-
8% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
7-hydroxy-6-methoxydihydrocoumarin + H2O
3-(2,3-dihydroxy-3-methoxyphenyl)propionic acid
show the reaction diagram
-
43% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
7-hydroxydihydrocoumarin + H2O
?
show the reaction diagram
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most rapidly hydrolyzed
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-
?
delta-D-gluconolactone + H2O
D-gluconate
show the reaction diagram
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0.8% of the activity compared to 7-hydroxydihydrocoumarin
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-
?
delta-valerolactone + H2O
5-hydroxypentanoate
show the reaction diagram
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0.3% of the activity compared to 7-hydroxydihydrocoumarin
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-
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
show the reaction diagram
dihydrocoumarin + H2O
melilotate
show the reaction diagram
dimethyl-(R)-methylsuccinate + H2O
(R)-methylsuccinate + methanol
show the reaction diagram
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
show the reaction diagram
DL-methyl-2-chloropropionate + H2O
2-chloropropionate + methanol
show the reaction diagram
gentisic acid gamma-lactone
?
show the reaction diagram
methyl cetraxate hydrochloride + H2O
cetraxate hydrochloride + methanol
show the reaction diagram
methyl-(R)-3-bromo-2-methylpropionate + H2O
(R)-3-bromomethylpropionate + methanol
show the reaction diagram
methyl-3(4-hydroxyphenyl)-propionate + H2O
3-(4-hydroxyphenyl)-propionate + methanol
show the reaction diagram
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18.5% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
methyl-DL-beta-acetylthioisobutyrate + H2O
D-beta-acetylthioisobutyrate + methanol
show the reaction diagram
peracetic acid
acetic acid + H2O
show the reaction diagram
additional information
?
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no hydrolysis with gamma-butyrolactone as substrate
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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
3,4-dihydrocoumarin + H2O
?
show the reaction diagram
3,4-dihydrocoumarin + H2O
melilotate
show the reaction diagram
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
show the reaction diagram
dihydrocoumarin + H2O
melilotate
show the reaction diagram
peracetic acid
acetic acid + H2O
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CaCl2
-
no effect at a concentration of 3.3 mM
CoCl2
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23% inhibition at a concentration of 1.6 mM
CuSO4
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100% inhibition at a concentration of 3.3 mM
delta-D-gluconolactone
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no effect at a concentration of 3.3 mM
diisopropyl fluorophosphate
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1 mM, complete inhibition
HgCl2
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1 mM, complete inhibition
iodoacetamide
-
no effect at a concentration of 3.3 mM
MgCl2
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no effect at a concentration of 3.3 mM
MnCl2
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no effect at a concentration of 3.3 mM
NaF
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20% inhibition at a concentration of 3.3 mM
NiCl2
-
54% inhibition at a concentration of 3.3 mM
phenylmethanesulfonyl fluoride
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1 mM, 54% inhibition
ZnCl2
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85% inhibition at a concentration of 3.3 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.81
2-coumaranone
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pH 7.0, 60°C
0.8 - 0.996
3,4-dihydrocoumarin
0.81
3,4-dihydroxycoumarin
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30°C, pH 7.0
0.24
dihydrocoumarin
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54.1
dimethyl-(R)-methylsuccinate
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pH 7.0
25.9
DL-beta-acetylthioisobutyrate methyl ester
0.66
gentisic acid gamma-lactone
-
pH 7.0, 60°C
6.88
methyl cetraxate hydrochloride
2.54
methyl-3-(4-hydroxyphenyl)-propionate
-
pH 7.0
25.9
methyl-DL-beta-acetylthioisobutyrate
-
pH 7.0
0.39
peracetic acid
30°C, pH 5.0
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1670
dihydrocoumarin
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
14.3
monochlordimedonbrominating activity, recombinant enzyme
15.8
-
purified enzyme, pH 7.0, 60°C
99.5
-
from fluorene-induced cells
116
3,4-dihydrocoumarin hydrolysis, recombinant enzyme
199
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bromination of 2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon
1500
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3,4-dihydrocoumarin hydrolysis
1636
-
dihydrocoumarin as substrate, after a 4-step purification
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.8 - 8.2
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 10.5
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approx. 50% of maximal activity at pH 5.0, approx. 40% of maximal activity at pH 10.0
5.5 - 9
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activity range, high activity at pH 6.0-8.0, profile overview
7 - 9
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pH 7: 70% of the maximal activity, pH 9: 40% of the maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 60
-
approx. 90% of maximal activity at 20°C, approx. 40% of maximal activity at 60°C
30 - 80
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activity range, high activity at 50-65°C, profile overview
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
22 micromole/min activity per g fresh weight
Manually annotated by BRENDA team
-
64 micromole/min activity per g fresh weight
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
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gel filtration
70000
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gel filtration
75000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8 - 9
-
no loss of activity after 2 h in buffers at 0°C
94343
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 80
-
no loss of activity after 30 min below 75°C, 31% loss of activity after 30 min at 80°C
55
-
stable to heating for 10 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10°C, acetone powder from seedlings, over 6 months, less than 10% loss of activity
-
-10°C, at pH 7, preparations containing more than 5 mg per ml of protein, 12 months, less than 10% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, DEAE-Sephacel, Phenyl-Superose, Superdex 200
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native enzyme from strain G27 186fold to homogeneity by ammonium sulfate fractionation, anion exchange chromatography, and gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is induced by growth on 1-naphthol, although not by growth on D-glucose, benzoic acid, or succinate