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
3.2.1.117
-
RECOMMENDED NAME
GeneOntology No.
amygdalin beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
extracellular enzyme that shows amygdalin as well as prunasin hydrolase activity
-
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
four isoforms found, AH I, AH I', AH II, AH II'
-
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
extracellular enzyme that shows amygdalin as well as prunasin hydrolase activity; prunasin hydrolysis is much slower than amygdalin hydrolysis
-
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
high similarities with glycoside hydrolase family 1 enzymes
Q945G7
(R)-amygdalin + H2O = (R)-prunasin + D-glucose
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hydrolysis of O-glycosyl bond
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
amygdalin and prunasin degradation
-
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).
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
AH I'
-
-
-
-
AH II'
-
-
-
-
amygdalase
-
-
-
-
amygdalin glucosidase
-
-
-
-
amygdalin hydrolase
-
-
-
-
amygdalin hydrolase
-
-
amygdalin hydrolase isozyme I'
-
-
-
-
amygdalin hydrolase isozyme II'
-
-
-
-
amygdalinase
-
-
-
-
beta-glucosidase
-
-
beta-glucosidase
Dekkera bruxellensis LD72
-
-
-
beta-glucosidase
-
-
glucosidase
-
-
glycoside hydrolase
-
-
glycoside hydrolase
Dekkera bruxellensis LD72
-
-
-
glycoside hydrolase
-
-
CAS REGISTRY NUMBER
COMMENTARY
51683-43-3
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
strain LD72
-
-
Manually annotated by BRENDA team
Dekkera bruxellensis LD72
strain LD72
-
-
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
cultivars S3067 and Ramillete
-
-
Manually annotated by BRENDA team
var. sativa
-
-
Manually annotated by BRENDA team
Ehrh., black cherry
-
-
Manually annotated by BRENDA team
Saccharomycopsis fibuligera LU677
strain LU677
-
-
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
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
Q945G7
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
very broad specificity
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
Q945G7
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
amygdalin is decomposed by beta-glucosidase in the digestive fluid into glucose and prunasin, which is further hydrolyzed to mandelonitrile and then to benzaldehyde and hydrogen cyanide. Amygdalin, a toxic component, can cause fatal cyanide poisonings, chronic toxicity, and death, substrate and product determination in the in vitro system by mass spectrometry, method, overview
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
Saccharomycopsis fibuligera LU677
-
-, first step of cyanogenesis from amygdalin
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
-
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
very effective substrate, EC 3.2.1.118 activity
-
?
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
Dekkera bruxellensis, Dekkera bruxellensis LD72
-
is partially hydrolysed
-
-
?
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
Dekkera bruxellensis, Dekkera bruxellensis LD72
-
refermentation of a sour cherry juice supplemented beer
-
-
?
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 ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
Q945G7
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
first step of cyanogenesis from amygdalin
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
-
amygdalin is decomposed by beta-glucosidase in the digestive fluid into glucose and prunasin, which is further hydrolyzed to mandelonitrile and then to benzaldehyde and hydrogen cyanide. Amygdalin, a toxic component, can cause fatal cyanide poisonings, chronic toxicity, and death
-
-
?
(R)-amygdalin + H2O
(R)-prunasin + D-glucose
show the reaction diagram
Saccharomycopsis fibuligera LU677
-
first step of cyanogenesis from amygdalin
-
?
amygdalin + H2O
prunasin + D-glucose
show the reaction diagram
-
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
glucono-delta-lactone
-
complete inhibition at 1 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1.65
-
(R)-amygdalin
-
AH II'
1.88
-
(R)-amygdalin
-
AH II
2.01
-
(R)-amygdalin
-
AH I
2.2
-
(R)-amygdalin
-
AH I'
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.5
5.5
-
all isoforms
6
-
-
both isoforms
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
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
-
procambial cells
Manually annotated by BRENDA team
-
cotyledons
Manually annotated by BRENDA team
-
procambial cells
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 ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Saccharomycopsis fibuligera LU677
-
-
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
62000
-
-
SDS-PAGE
62000
-
-
AH I; SDS-PAGE
66400
-
-
PG II, SDS-PAGE
147000
-
-
PG II, gel filtration
247000
-
-
PG I, gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
monomer
-
1 * 60000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
glycoprotein
-
-
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
55
-
-
PG I, half life: 2 h
60
-
-
PG II, half life: 7 h
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
4°C, 10 mM histidine-HCl buffer, pH 6.0
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
four isoforms
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
AH I expressed in Pichia pastoris
Q945G7
AH I, two clones of near full length cDNA
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
G394D
Q945G7
enhanced activity
S216H
Q945G7
enhanced activity
S216H/G394D
Q945G7
decreased activity
S216H/Y220I
Q945G7
enhanced activity
S216H/Y220I/G394D
Q945G7
decreased activity
S220I/G394D
Q945G7
decreased activity, EC 3.2.1.118 activity detected
Y220I
Q945G7
enhanced activity
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
brewing
-
importance and role of certain Brettanomyces species in the production of fruit lambic beers such as Kriek
brewing
Dekkera bruxellensis LD72
-
importance and role of certain Brettanomyces species in the production of fruit lambic beers such as Kriek
-
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