Information on EC 3.2.1.118 - prunasin beta-glucosidase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY
3.2.1.118
-
RECOMMENDED NAME
GeneOntology No.
prunasin beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(R)-prunasin + H2O = D-glucose + mandelonitrile
show the reaction diagram
extracellular enzyme that shows amygdalin as well as prunasin hydrolase activity, prunasin hydrolysis is much slower than amygdalin hydrolysis; two isoforms found, PG I and PG II
-
(R)-prunasin + H2O = D-glucose + mandelonitrile
show the reaction diagram
extracellular enzyme that shows amygdalin as well as prunasin hydrolase activity, prunasin hydrolysis is much slower than amygdalin hydrolysis
-
(R)-prunasin + H2O = D-glucose + mandelonitrile
show the reaction diagram
five isoforms found, PH1-PH5, high sequence similarities with glucoside hydrolase family 1 enzymes
-
(R)-prunasin + H2O = D-glucose + mandelonitrile
show the reaction diagram
three isoforms found, PH I, PH IIa, PH IIb
-
(R)-prunasin + H2O = D-glucose + mandelonitrile
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
-
Biosynthesis of secondary metabolites
-
Cyanoamino acid metabolism
-
SYSTEMATIC NAME
IUBMB Comments
prunasin beta-D-glucohydrolase
Highly specific; does not act on amygdalin, linamarin or gentiobiose. (cf. EC 3.2.1.21 beta-glucosidase).
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
beta-glucosidase
-
-
hydrolase, prunasin
-
-
-
-
PH I
-
-
-
-
PH IIa
-
-
-
-
PH IIb
-
-
-
-
prunasin hydrolase
-
-
-
-
prunasin hydrolase
-
-
prunasin hydrolase isozyme I
-
-
-
-
prunasin hydrolase isozyme IIa
-
-
-
-
prunasin hydrolase isozyme IIb
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9023-41-0
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
plum, var. Stanley
-
-
Manually annotated by BRENDA team
; four different genotypes with different degrees of bitterness
-
-
Manually annotated by BRENDA team
cultivars S3067 and Ramillete
-
-
Manually annotated by BRENDA team
Ehrh., black cherry
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
metabolism
-
amygdalin is hydrolyzed to prunasin by the amygdalin hydrolase, EC 3.2.1.117, and further hydrolyzed by the prunasin hydrolase to mandelonitrile
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
slow reaction
-
?
(R)-prunasin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
in the sweet genotype Ramillete, amygdalin formation is prevented because the prunasin is degraded upon passage of the beta-glucosidase rich cell layer in the inner epidermis of the tegument
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(S)-sambunigrin + H2O
D-glucose + mandelonitrile
show the reaction diagram
-
i.e. epimer of (R)-prunasin, poor substrate
-
-
?
2-nitrophenyl beta-D-glucopyranoside + H2O
2-nitrophenol + D-glucose
show the reaction diagram
-
very effective substrate
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucose
show the reaction diagram
-
-
-
-
?
4-nitrophenyl-beta-D-galactopyranoside + H2O
4-nitrophenol + D-galactose
show the reaction diagram
-
poor substrate
-
-
?
6-bromo-2-naphthyl-beta-D-glucopyranoside + H2O
?
show the reaction diagram
-
-
-
-
?
prunasin + H2O
D-mandelonitrile + beta-D-glucose
show the reaction diagram
-
-
-
-
?
prunasin + H2O
D-mandelonitrile + beta-D-glucose
show the reaction diagram
-
prunasin is taken up in the small intestine and decomposed by beta-glucosidase into glucose and mandelonitrile, which is further hydrolyzed to benzaldehyde and hydrogen cyanide. Amygdalin, the precursor of prunasin, is a toxic component and can cause fatal cyanide poisonings, chronic toxicity, and death, substrate and product determination in the in vitro system by mass spectrometry, method, overview
-
-
?
salicin + H2O
D-glucose + salicyl alcohol
show the reaction diagram
-
very poor substrate
-
-
?
6-bromo-2-napthyl-beta-D-glucopyranoside + H2O
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
no substrates are (R)-amygdalin, linamarin, (neo)linustatin, 4-nitrophenyl-alpha-D-glucopyranoside, 4-nitrophenyl-beta-D-mannoside, 4-nitrophenyl-alpha-D-mannoside, 4-nitrophenyl-beta-D-xyloside and (S)-dhurrin
-
-
-
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)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
-
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
(R)-prunasin + H2O
mandelonitrile + D-glucose
show the reaction diagram
-
involved in cyanogenesis from (R)-amygdalin
-
?
prunasin + H2O
D-mandelonitrile + beta-D-glucose
show the reaction diagram
-
-
-
-
?
prunasin + H2O
D-mandelonitrile + beta-D-glucose
show the reaction diagram
-
prunasin is taken up in the small intestine and decomposed by beta-glucosidase into glucose and mandelonitrile, which is further hydrolyzed to benzaldehyde and hydrogen cyanide. Amygdalin, the precursor of prunasin, is a toxic component and can cause fatal cyanide poisonings, chronic toxicity, and death
-
-
?
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2-mercaptoethanol
-
weak inhibition
castanospermine
-
PH I and PH IIb, competitive
DTT
-
weak inhibition
iodoacetamide
-
weak inhibition
iodoacetic acid
-
weak inhibition
Mandelamide
-
weak inhibition
p-Chloromercuriphenylsulfonate
-
weak inhibition
p-hydroxymandelic acid
-
weak inhibition
Mandelic acid
-
weak inhibition
additional information
-
little or no inhibition by Cu2+, Mg2+, Zn2+, Pb2+, Fe2+, Fe3+, Ag2+, no inhibition by diethyldithiocarbamate, 1,10-phenanthroline, 2,2'-dipyridyl or EDTA
-
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.09
-
castanospermine
-
PH IIb, pH 5, 30C
0.19
-
castanospermine
-
PH I, pH 5, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.26
-
-
purified PG I, pH 6, 25C
1.11
-
-
purified PG II, pH 6, 25C
2.8
-
-
purified PH I
4.9
-
-
purified PH II
12.26
-
-
purified enzyme, pH 6, 25C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
-
-
all isoforms
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4
7
-
all isoforms, half maximum activity
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
-
high activity in the inner epidermis of the tegument of the sweet genotype Ramillete, whereas the bitter cultivar S3067 shows low activity in this cell layer; in the sweet genotype, the inner epidermis in the tegument facing the nucellus is rich in cytoplasmic and vacoular prunasin beta-glucosidase activity, whereas in the bitter cultivar, the beta-glucosidase activity in this cell layer is low. In the bitter genotype, prunasin synthesized in the tegument is transported into the cotyledon via the transfer cells and converted into amygdalin in the developing almond seed, whereas in the sweet genotype, amygdalin formation is prevented because the prunasin is degraded upon passage of the beta-glucosidase rich cell layer in the inner epidermis of the tegument
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
-
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
-
localization analysis by immunohistochemic method. 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
-
high activity in the inner epidermis in the tegument of the sweet genotype Ramillete; in the sweet genotype, the inner epidermis in the tegument facing the nucellus is rich in cytoplasmic and vacoular prunasin beta-glucosidase activity, whereas in the bitter cultivar, the beta-glucosidase activity in this cell layer is low
Manually annotated by BRENDA team
-
high activity in the inner epidermis in the tegument of the sweet genotype Ramillete; in the sweet genotype, the inner epidermis in the tegument facing the nucellus is rich in cytoplasmic and vacoular prunasin beta-glucosidase activity, whereas in the bitter cultivar, the beta-glucosidase activity in this cell layer is low
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
58800
-
-
PG I, SDS-PAGE
60000
-
-
SDS-PAGE
62080
-
-
calculated from known amino acid sequence
66400
-
-
PG II, SDS-PAGE
68000
-
-
PH IIb and PH I, native PAGE
68000
-
-
SDS-PAGE
68000
-
-
PH IIb and PH I, gel filtration, SDS-PAGE
69500
-
-
PH IIa, native PAGE
69500
-
-
PH IIa, SDS-PAGE
140000
-
-
PH IIa, native PAGE
140000
-
-
PH IIa, gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-
2 * 69500, SDS-PAGE
monomer
-
1 * 68000, SDS-PAGE, PH I and PH IIb
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
glycoprotein
-
-
glycoprotein
-
all isoforms
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C lyophylized powder
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
PH I and PH II can be completely resolved by hydroxyapatite chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
PH1-PH5 genes, PH2 expressed in Pichia pastoris
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
nutrition
-
in the sweet almond genotype, the inner epidermis in the tegument facing the nucellus is rich in cytoplasmic and vacuolar prunasin beta-glucosidase activity, whereas in the bitter cultivar, the beta-glucosidase activity in this cell layer is low. In the bitter genotype, prunasin synthesized in the tegument is transported into the cotyledon via the transfer cells and converted into amygdalin in the developing almond seed, whereas in the sweet genotype, amygdalin formation is prevented because the prunasin is degraded upon passage of the beta-glucosidase rich cell layer in the inner epidermis of the tegument
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
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
food industry
-
beta-glucosidase as a tool in marker-assisted selection against bitter almonds