Information on EC 3.1.1.42 - chlorogenate hydrolase

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

EC NUMBER
COMMENTARY hide
3.1.1.42
-
RECOMMENDED NAME
GeneOntology No.
chlorogenate hydrolase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
chlorogenate + H2O = caffeate + quinate
show the reaction diagram
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-
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-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
transesterification
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chlorogenic acid degradation
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-
SYSTEMATIC NAME
IUBMB Comments
chlorogenate hydrolase
Also acts, more slowly, on isochlorogenate. No other substrates are known.
CAS REGISTRY NUMBER
COMMENTARY hide
74082-59-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene HcaG
SwissProt
Manually annotated by BRENDA team
Aspergillus sojae AKU 3312
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
isolated from human colonic microflora
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-
Manually annotated by BRENDA team
3 strains isolated from human colonic microflora
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-
Manually annotated by BRENDA team
2 strains isolated from human colonic microflora
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-
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
1-phenylethyl alcohol + 5-chlorogenic acid
(S)-1-phenylethyl caffeate + quinate
show the reaction diagram
-
-
transesterification reaction, about 50% molar conversion yield
-
?
2-phenylethyl alcohol + 5-chlorogenic acid
2-phenylethyl caffeate + quinate
show the reaction diagram
-
-
transesterification reaction, about 50% molar conversion yield
-
?
2-phenylethyl bromide + 5-chlorogenic acid
2-phenylethyl caffeate + 5-bromo-quinate
show the reaction diagram
-
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substitution reaction, about 2.3% molar conversion yield, no substrate: phenylethyl chloride, phenylethyl iodide
-
?
3,5-di-O-caffeylquinic acid + H2O
?
show the reaction diagram
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-
-
-
?
3-(3,4-dihydroxyphenyl)-propionic acid + 1-phenylethyl alcohol
?
show the reaction diagram
-
-
-
-
?
5-caffeoylquinic acid
methyl caffeate + quinate
show the reaction diagram
-
-
different structures of substrates for synthesis of methyl caffeate with chlorogenate hydrolase, overview
-
?
chlorogenate + H2O
caffeate + quinate
show the reaction diagram
chlorogenic acid + H2O
?
show the reaction diagram
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-
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-
chlorogenic acid + H2O
caffeate + quinate
show the reaction diagram
cinnamic acid ethylester + H2O
cinnamic acid + ethanol
show the reaction diagram
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-
-
-
?
isochlorogenate + H2O
?
show the reaction diagram
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-
?
p-coumaric acid + 2-phenylethyl bromide
2-phenylethyl p-coumarate + bromide
show the reaction diagram
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about 90% molar conversion yield
-
?
phenylpropyl bromide + 5-chlorogenic acid
(S)-1-phenylpropyl caffeate + 5-bromo-quinate
show the reaction diagram
-
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about 2.3% molar conversion yield
-
r
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
chlorogenate + H2O
caffeate + quinate
show the reaction diagram
chlorogenic acid + H2O
caffeate + quinate
show the reaction diagram
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
caffeate
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diisopropylphosphofluoridate
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-
additional information
-
no substrate inhibition
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
coffee powder, coffee pulp
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 6.5
chlorogenic acid
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
22
chlorogenic acid
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37░C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.09
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cell-free extract
0.34
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purification step DEAE-cellulose
0.36
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commercial preparation, pH 6.5, 40░C
0.67
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purification step CM-Sephadex C-50
4.55
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purification step hydroxyapatite
6.2
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37░C
24.11
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purification step Sephadex G-200
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
activity assay
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 8
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less than 50% of maximal activity above and below
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
activity assay
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 100
-
assay range, in 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55000
determined by gel filtration and alternatively by mass spectrometry with matrix assisted laser desorption and ionization time-of-flight mass spectrometers
60000
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4 * 60000, amino acid analysis
80000
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2 * 80000, SDS-PAGE
88000
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determined by SDS-PAGE, monomer
170000
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gel filtration
180000
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determined by gel filtration, homodimer
240000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
-
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tetramer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
side-chain modification
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glycoprotein
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3 - 9
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pH 3.0: 80% residual activity after 10 min, pH 9.0: 65% residual activity after 10 min
80932
3.8 - 7.8
stable for 90 min
671497
5.5 - 7
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stable within this range
665775
7
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highest stability
80932
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
stable up to
45
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10 min, 27% loss of activity
50
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10 min, 84% loss of activity
55
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stable up to
65
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85% inactivation after 10 min
75
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complete inactivation
80
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inactivation
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
chlorogenate hydrolase is purifried from mycelia of Aspergillus sojae using a DEAE-cellulose, a CM-Sephadex C-50, a hydroxyapatite and a Sephadex G-200 column
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene hcaG, organized in the chromosomal cluster dca-pca-qui-pob-hca, genomic organization and chromosomal location, DNA sequence determination and analysis
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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development of a convenient one-pot procedure for conversion of 5-caffeoylquinic acid, from coffee beans, to 3-cyclohexylpropyl caffeate, which exhibits an antiproliferative effect toward various human tumor cells. The procedure comprises of two consecutive reactions by chlorogenate hydrolase from Aspergillus japonicus and Candida antarctica lipase B, and is performed using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as the reaction solvent, method optimization, overview. The system provides 12.8 mM 3-cyclohexylpropyl caffeate from 15 mM 5-caffeoylquinic acid with conversion yield of 85.3%. The reaction scarcely proceeds in 1-butyl-3-methylimidazolium tetrafluoroborate, evaluation of several ionic liquids, overview