Information on EC 3.2.1.119 - vicianin beta-glucosidase

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The expected taxonomic range for this enzyme is: Euphyllophyta

EC NUMBER
COMMENTARY
3.2.1.119
-
RECOMMENDED NAME
GeneOntology No.
vicianin beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(R)-vicianin + H2O = mandelonitrile + vicianose
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hydrolysis of O-glycosyl bond
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
vicianin bioactivation
-
SYSTEMATIC NAME
IUBMB Comments
(R)-vicianin beta-D-glucohydrolase
Also hydrolyses, more slowly, (R)-amygdalin and (R)-prunasin, but not gentiobiose, linamarin or cellobiose.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
vicianin hydrolase
-
-
-
-
vicianin hydrolase
A2SY66
-
CAS REGISTRY NUMBER
COMMENTARY
91608-93-4
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
; Squirrel's foot fern, var. Blume
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-amygdalin + H2O
mandelonitrile + beta-gentiobiose
show the reaction diagram
-
reaction 16% of the rate of vicianine hydrolysis
-
-
?
(R)-amygdalin + H2O
mandelonitrile + beta-gentiobiose
show the reaction diagram
-
reaction 27% of the rate of vicianine hydrolysis
-
-
?
(R)-amygdalin + H2O
(R)-mandelonitrile + beta-gentiobiose
show the reaction diagram
-
-
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
reaction 12% of the rate of vicianine hydrolysis
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
reaction 14% of the rate of vicianine hydrolysis
-
-
?
(R)-vicianin + H2O
mandelonitrile + vicianose
show the reaction diagram
-
-
-
-
?
(R)-vicianin + H2O
mandelonitrile + vicianose
show the reaction diagram
-
i.e. beta-vicianoside of (R)-mandelonitrile, strict requirement for (R)-epimers, cyanogenic disaccharides preferred over monosaccharides, involved in catabolism of cyanogenic glycosides
-
-
?
2-phenylethyl beta-primeveroside + H2O
?
show the reaction diagram
A2SY66, -
-
-
-
?
o-nitrophenyl-beta-D-glucopyranoside + H2O
2-nitrophenol + beta-D-glucopyranose
show the reaction diagram
-
poor substrate
-
-
?
o-nitrophenyl-beta-D-xylopyranoside + H2O
2-nitrophenol + beta-D-xylopyranose
show the reaction diagram
-
poor substrate
-
-
?
p-nitrophenyl beta-primeveroside + H2O
?
show the reaction diagram
A2SY66, -
recombinant enzyme expressed in Escherichia coli does not hydrolyze p-nitrophenyl beta-primeveroside
-
-
?
p-nitrophenyl-beta-D-glucopyranoside + H2O
4-nitrophenol + beta-D-glucopyranose
show the reaction diagram
-
poor substrate
-
-
?
p-nitrophenyl-beta-D-xylopyranoside + H2O
4-nitrophenol + beta-D-xylopyranose
show the reaction diagram
-
poor substrate
-
-
?
prunasin + H2O
D-mandelonitrile + beta-D-glucose
show the reaction diagram
A2SY66, -
shows 34% of its vicianin hydrolase activity with prunasin
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-
?
vicianin + H2O
vicianose + D-mandelonitrile
show the reaction diagram
A2SY66, -
best substrate, recombinant protein shows the same pattern of substrate specificity as the native enzyme
-
-
?
furcatin + H2O
?
show the reaction diagram
A2SY66, -
recombinant enzyme expressed in Escherichia coli does not hydrolyze furcatin
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-
?
additional information
?
-
-
no substrates are lactose, o-nitrophenyl-beta-D-galactopyranoside, beta-methyl-D-glucoside, beta-gentiobiose, linamarin, cellobiose, p-nitrophenyl-alpha-D-glucopyranoside, salicin, phenyl-beta-D-glucoside, maltose and sucrose
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-
-
additional information
?
-
A2SY66, -
does not hydrolyze amygdalin, mandelonitrile-, 2-phenylethyl-, p-nitrophenyl beta-gentiobioside, p-nitrophenyl beta-D-xylopyranoside, p-nitrophenyl alpha-L-arabinopyranoside and p-nitrophenyl beta-D-galactopyranoside
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(R)-vicianin + H2O
mandelonitrile + vicianose
show the reaction diagram
-
involved in catabolism of cyanogenic glycosides
-
-
?
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Ag+
-
strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
castanospermine
-
indolizidine alkaloid, strong, with (R)-prunazin as substrate
Cu2+
-
strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
delta-gluconolactone
-
strong, with (R)-prunazin as substrate
diethyldithiocarbamate
-
weak, with p-nitrophenyl-beta-D-glucopyranoside as substrate
Fe2+
-
weak, with p-nitrophenyl-beta-D-glucopyranoside as substrate
-
p-Chloromercuriphenylsulfonate
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strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
Hg2+
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strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
additional information
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less than 10% inhibition by Ca2+, Zn2+, Fe3+, Co2+, Cd2+ and Pb2+, no inhibition by EDTA, 2,2'-dipyridyl, o-pheanthroline, 2-mercaptoethanol, dithiothreitol, iodacetic acid, iodoacetamide and N-methylmaleimide
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KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
3.2
-
(R)-Prunasin
-
30°C, pH 6
4.9
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(R)-Vicianin
-
30°C, pH 6
3.39
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p-nitrophenyl-beta-D-glucopyranoside
-
30°C, pH 6
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
1.05
-
A2SY66, -
crude extract
8.97
-
A2SY66, -
recombinant enzyme, activity against vicianin
9.86
-
A2SY66, -
native enzyme, purified, activity against vicianin
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
-
-
with p-nitrophenyl-beta-D-glucopyranoside as substrate
5.5
-
-
with (R)-vicianin as substrate
6
-
-
with (R)-prunazin as substrate
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
8.69
-
A2SY66, -
-
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
A2SY66, -
moderately present
Manually annotated by BRENDA team
A2SY66, -
slightly present
Manually annotated by BRENDA team
A2SY66, -
slightly present
Manually annotated by BRENDA team
A2SY66, -
abundantly present
Manually annotated by BRENDA team
A2SY66, -
slightly present
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
73000
-
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gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
A2SY66, -
1 * 56000, SDS-PAGE, 1 * 55616, sequence analysis
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
no glycoprotein
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
by gel filtration, 9.39fold
A2SY66, -
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli as a GST fusion protein, full-length cDNA subcloned into the pFastBac1 plasmid for expression in insect cells using a baculovirus expression system
A2SY66, -