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
LITERATURE
(R)-vicianin + H2O = mandelonitrile + vicianose
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of O-glycosyl bond
-
-
-
-
PATHWAY
BRENDA Link
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
COMMENTARY
LITERATURE
vicianin hydrolase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
91608-93-4
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
; Squirrel's foot fern, var. Blume
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
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
-
-
?
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
-
-
?
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
-
-
-
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
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
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
-
strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
Hg2+
-
strong, with p-nitrophenyl-beta-D-glucopyranoside as substrate
additional information
-
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
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3.2
(R)-Prunasin
-
30°C, pH 6
4.9
(R)-Vicianin
-
30°C, pH 6
3.39
p-nitrophenyl-beta-D-glucopyranoside
-
30°C, pH 6
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
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
ORGANISM
UNIPROT
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
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
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
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
73000
-
gel filtration
646668
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
A2SY66
1 * 56000, SDS-PAGE, 1 * 55616, sequence analysis
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
no glycoprotein
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by gel filtration, 9.39fold
A2SY66
Cloned/COMMENTARY
ORGANISM
UNIPROT
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