Information on EC 3.2.1.117 - amygdalin beta-glucosidase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
3.2.1.117
-
RECOMMENDED NAME
GeneOntology No.
amygdalin beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of O-glycosyl bond
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
amygdalin and prunasin degradation
-
-
Biosynthesis of secondary metabolites
-
-
Cyanoamino acid metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
amygdalin beta-D-glucohydrolase
Highly specific; does not act on prunasin, linamarin, gentiobiose or cellobiose (cf. EC 3.2.1.21 beta-glucosidase).
CAS REGISTRY NUMBER
COMMENTARY hide
51683-43-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
strain LD72
-
-
Manually annotated by BRENDA team
strain LD72
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Saccharomyces cerevisiae
strains LD25 and LD40
-
-
Manually annotated by BRENDA team
several strains, highest activity during stationary growth phase
-
-
Manually annotated by BRENDA team
plum, var. Stanley
-
-
Manually annotated by BRENDA team
strain LU677
-
-
Manually annotated by BRENDA team
strain LU677
-
-
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
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
6-bromo-2-naphthyl-beta-D-glucopyranoside + H2O
6-bromo-2-naphthol + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
?
amygdalin + H2O
?
show the reaction diagram
amygdalin + H2O
prunasin + D-glucose
show the reaction diagram
-
-
-
-
?
cardiospermin 5-sulfate + H2O
D-glucose + sulfuric acid mono-(3-cyano-3-hydroxy-2-methylenepropyl) ester
show the reaction diagram
-
poor substrate
-
-
?
dhurrin + H2O
D-glucose + 4-hydroxymandelonitrile
show the reaction diagram
-
-
-
-
?
epivolkenin + H2O
D-glucose + 1,4-dihydroxycyclopent-2-enecabonitrile
show the reaction diagram
-
poor substrate
-
-
?
gynocardin + H2O
D-glucose + 1,4,5-hydroxycyclopent-2-enecarbonitrile
show the reaction diagram
-
-
-
-
?
linamarin + H2O
D-glucose + acetone cyanohydrin
show the reaction diagram
-
poor substrate
-
-
?
lucumin + H2O
?
show the reaction diagram
-
poor substrate
-
-
?
passibiflorin + H2O
D-glucose + 1,4-dihydroxycyclopent-2-enecabonitrile
show the reaction diagram
-
poor substrate
-
-
?
sambunigrin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
very effective substrate
-
-
?
sour cherry glycoside + H2O
benzaldehyde + eugenol + trans-isoeugenol + cis-isoeugenol + geraniol + ?
show the reaction diagram
sour cherry glycoside + H2O
benzaldehyde + linalool + eugenol + ?
show the reaction diagram
taxiphyllin + H2O
D-glucose + 4-hydroxymandelonitrile
show the reaction diagram
-
-
-
-
?
tetraphyllin B + H2O
D-glucose + 1,4-dihydroxycyclopent-2-enecabonitrile
show the reaction diagram
-
very effective substrate
-
-
?
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
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
amygdalin + H2O
prunasin + D-glucose
show the reaction diagram
-
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
glucono-delta-lactone
-
complete inhibition at 1 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.65 - 2.2
(R)-amygdalin
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.45
-
purified AH II'
0.48
-
purified AH I' and AH II
0.58
-
purified AH I
6.5
-
cotyledon extract
9.9
-
embryonic axes
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 5.5
-
all isoforms
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
TC7 clone
Manually annotated by BRENDA team
-
around the vascular tissue in the root/stem axis of the embryo
Manually annotated by BRENDA team
-
amygdalin contents in different genotypes, i.e. cultivars Ramillete, Marcona, Garrigues, and S3067, the content is high in bitter variants such as S3067, and low in sweet variants such as Ramillete, overview
Manually annotated by BRENDA team
-
in the new developing cambial cells in the primordial leaves
Manually annotated by BRENDA team
-
use of a simulated in vitro salivary-gastric-small intestinal digestion model system
Manually annotated by BRENDA team
additional information
-
the staining method using 6-bromo-2-naphthyl-beta-D-glucopyranoside does not distinguish between beta-glycosidases with different substrate specificity, like prunasin and amygdalin hydrolase
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000
-
all isoforms, gel filtration
58800
-
PG I, SDS-PAGE
60000
-
all isoforms, SDS-PAGE
60300
-
AH I, calculated from known amino acid sequence
66400
-
PG II, SDS-PAGE
147000
-
PG II, gel filtration
247000
-
PG I, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 60000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
-
PG I, half life: 2 h
60
-
PG II, half life: 7 h
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 10 mM histidine-HCl buffer, pH 6.0
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
four isoforms
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AH I expressed in Pichia pastoris
AH I, two clones of near full length cDNA
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G394D
enhanced activity
S216H
enhanced activity
S216H/G394D
decreased activity
S216H/Y220I
enhanced activity
S216H/Y220I/G394D
decreased activity
S220I/G394D
decreased activity, EC 3.2.1.118 activity detected
Y220I
enhanced activity
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
brewing
diagnostics
-
evaluating intestinal absorption of amygdalin or prunasin, by estimating its transfer across the mucosal border as well as its uptake into the intestinal tissue, for judgement of toxication rusks, overview. Use of the enzyme in an in vitro digestion model with the Caco-2 cell to estimate the human oral bioavailability of cyanogenic compounds from food or plants, overview
medicine
-
chemotherapy, conjugate with antibody