Information on EC 3.2.1.161 - beta-apiosyl-beta-glucosidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.2.1.161
-
RECOMMENDED NAME
GeneOntology No.
beta-apiosyl-beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
7-[beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranosyloxy]isoflavonoid + H2O = a 7-hydroxyisoflavonoid + beta-D-apiofuranosyl-(1->6)-D-glucose
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis
-
beta-glycosidic bond between glycogen and aglycone of disaccharide glycosides, no hydrolysis of bond of two saccharides, barely active on monosaccharide glycosides
hydrolysis of O-glycosyl bond
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
dalpatein and dalnigrein biosynthesis
-
-
furcatin degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
7-[beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranosyloxy]isoflavonoid beta-D-apiofuranosyl-(1->6)-D-glucohydrolase
The enzyme from the tropical tree Dalbergia nigrescens Kurz belongs in glycosyl hydrolase family 1. The enzyme removes disaccharides from the natural substrates dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside and 7-hydroxy-2',4',5',6-tetramethoxy-7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside (dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside) although it can also remove a single glucose residue from isoflavonoid 7-O-glucosides [2]. Daidzin and genistin are also substrates.
CAS REGISTRY NUMBER
COMMENTARY hide
1000598-83-3
-
39346-29-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Blume
SwissProt
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
2-methyl-4'-nitro-isoflavone 7-O-beta-D-glucopyranoside + H2O
2-methyl-4'-nitro-isoflavone + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
2-nitrophenyl beta-D-glucopyranoside + H2O
2-nitrophenol + D-glucopyranose
show the reaction diagram
-
-
-
-
ir
2-phenylethyl beta-primeveroside + H2O
2-phenylethanol + 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
show the reaction diagram
4-allylphenyl beta-D-glucoside + H2O
4-allylphenol + beta-D-glucose
show the reaction diagram
-
pAP beta-glucoside, 2 mM substrate, 37°C, 20 mM sodium citrate buffer, pH 5.0
-
-
?
4-methylumbelliferyl beta-D-glucoside + H2O
4-methylumbelliferol + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
4-nitrophenyl beta-D-fucoside + H2O
4-nitrophenol + beta-D-fucose
show the reaction diagram
-
-
-
-
ir
4-nitrophenyl beta-D-galactopyranoside + H2O
4-nitrophenol + beta-D-galactopyranose
show the reaction diagram
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
show the reaction diagram
4-nitrophenyl beta-D-mannopyranoside + H2O
4-nitrophenol + beta-D-mannopyranose
show the reaction diagram
-
-
-
-
ir
4-nitrophenyl beta-D-thioglucopyranoside + H2O
4-nitrophenol + beta-D-thioglucopyranose
show the reaction diagram
-
-
-
-
ir
4-nitrophenyl beta-D-xylopyranoside + H2O
4-nitrophenol + beta-D-xylopyranose
show the reaction diagram
-
-
-
-
ir
4-nitrophenyl-alpha-L-arabinopyranoside + H2O
4-nitrophenol + alpha-L-arabinopyranose
show the reaction diagram
-
-
-
-
ir
apigenin 7-O-beta-D-glucopyranoside + H2O
apigenin + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
beta-allylphenyl-beta-D-glucopyranoside + H2O
4-allylphenol + beta-D-glucopyranose
show the reaction diagram
biochanin A 7-O-beta-D-glucopyranoside + H2O
biochanin A + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
biochanin A 7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
biochanin A + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
daidzin + H2O
daidzein + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalcochinin-8'-O-beta-D-glucopyranoside + H2O
dalcochinin + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside + H2O
dalnigrein + beta-D-apiofuranosyl-(1->6)-D-glucose + H+
show the reaction diagram
-
-
-
?
dalpaniculin-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
dalpaniculin + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside + H2O
dalpatein + beta-D-apiofuranosyl-(1->6)-D-glucose + H+
show the reaction diagram
-
-
-
?
dalpatein-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
dalpatein + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
formononetin 7-O-beta-D-glucopyranoside + H2O
formononetin + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
?
furcatin + H2O
4-allylphenol + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
genistin + H2O
genistein + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
p-allylphenyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside + H2O
p-allylphenol + 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside
show the reaction diagram
-
pAP furcatin, 2 mM substrate, 37°C, 20 mM sodium citrate buffer, pH 5.0
aglycon product acts as insect deterrent
-
?
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
p-nitrophenol + 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
show the reaction diagram
-
pNP beta-primeveroside, 2 mM substrate, 37°C, 20 mM sodium citrate buffer, pH 5.0, measurement of kinetic parameters
-
-
?
p-nitrophenyl beta-D-glucoside + H2O
p-nitrophenol + D-glucose
show the reaction diagram
-
2 mM substrate, 37°C, 20 mM sodium citrate buffer, pH 5.0
-
-
?
p-nitrophenyl beta-gentiobioside + H2O
4-nitrophenol + beta-gentiobiose
show the reaction diagram
p-nitrophenyl beta-primeveroside + H2O
4-nitrophenol + 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
show the reaction diagram
87.3% of the activity with furcatin
-
-
?
vicianin + H2O
mandelonitrile + 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranose
show the reaction diagram
4.99% of the activity with furcatin
-
-
?
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
biochanin A 7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
biochanin A + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
daidzin + H2O
daidzein + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalcochinin-8'-O-beta-D-glucopyranoside + H2O
dalcochinin + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside + H2O
dalnigrein + beta-D-apiofuranosyl-(1->6)-D-glucose + H+
show the reaction diagram
A3RF67
-
-
-
?
dalpaniculin-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
dalpaniculin + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside + H2O
dalpatein + beta-D-apiofuranosyl-(1->6)-D-glucose + H+
show the reaction diagram
A3RF67
-
-
-
?
dalpatein-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O
dalpatein + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
genistin + H2O
genistein + beta-D-glucopyranose
show the reaction diagram
-
-
-
-
ir
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
FeSO4, CaCl2, HgCl2, MnCl2, ZnSO4 have no effect on the activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-nitrophenol
-
1 mM, 25% inhibition
Ag+
-
1 mM, 80% inhibition
D-glucono-1,5-lactone
-
1 mM, 50% inhibition
ethyleneglycol monomethyl ether
-
weak
glycerol
-
weak
Hg2+
-
strong
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.07
2-methyl-4'-nitro-isoflavone 7-O-beta-D-glucopyranoside
-
isoenzyme R3
0.7 - 1
2-Nitrophenyl-beta-D-glucopyranoside
0.17 - 0.2
4-methylumbelliferyl beta-D-glucoside
1.8
4-nitrophenyl-beta-D-fucoside
-
-
2 - 3
4-nitrophenyl-beta-D-galactopyranoside
1.5 - 14.7
4-nitrophenyl-beta-D-glucopyranoside
0.05
apigenin 7-O-beta-D-glucopyranoside
-
isoenzyme R3, isoenzyme L1
0.02
biochanin A 7-O-beta-D-glucopyranoside
-
-
0.15 - 0.2
biochanin A 7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]
0.11
daidzin
-
-
4
dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
pH 5.5, 30°C, recombinant Dnbglu2
0.7
dalpaniculin-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]
-
-
3.8
dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
pH 5.5, 30°C, recombinant Dnbglu2
0.5
dalpatein-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]
-
-
2.2
furcatin
pH 6.0, 37°C
0.09
genistin
-
-
1.7 - 7.5
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
5.1
p-nitrophenyl beta-primeveroside
pH 6.0, 37°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7
4-nitrophenyl-beta-D-fucoside
Dalbergia nigrescens
-
-
10.4
4-nitrophenyl-beta-D-glucopyranoside
Dalbergia nigrescens
-
-
480
daidzin
Dalbergia nigrescens
-
-
229
dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
Dalbergia nigrescens
A3RF67
pH 5.5, 30°C, recombinant Dnbglu2
334
dalpaniculin-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]
Dalbergia nigrescens
-
-
20
dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
Dalbergia nigrescens
A3RF67
pH 5.5, 30°C, recombinant Dnbglu2
465
dalpatein-7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]
Dalbergia nigrescens
-
-
500
genistin
Dalbergia nigrescens
-
-
0.005 - 0.098
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
58.6
dalnigrein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
Dalbergia nigrescens
A3RF67
pH 5.5, 30°C, recombinant Dnbglu2
42469
5.32
dalpatein 7-O-beta-D-apiofuranosyl-(1->6)-beta-D-glucopyranoside
Dalbergia nigrescens
A3RF67
pH 5.5, 30°C, recombinant Dnbglu2
42468
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.27
-
wild-type enzyme with substrate furcatin, release of p-allylphenol
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 5
-
and a second optimum at pH 7-7.5
7 - 7.5
-
and a second optimum at pH 4.5-5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3.5 - 6.5
-
less than half-maximal activity above and below
4 - 10
recombinant enzyme is active over the range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60510
monomer, calculated from protein sequence
68000
-
2 * 68000, SDS-PAGE
88000
-
SDS-PAGE of eluted fractions
125000 - 135000
-
gel filtration, sucrose density gradient centrifugation
240000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 68000, SDS-PAGE
tetramer
-
4 * 62000-63000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
stable below
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE anion exchange chromatograpy, gel filtration
-
purification of supernatant with glutathion-Sepharose column after centrifugation of cell lysate
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Escherichia coli BL21 transformed with expression plasmid pGEX
-
expressed in Pichia pastoris
expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A419V
-
furcatin: 40%, pNP beta-primeveroside: 78% and kcat/Km (min-1 * mM-1) = 1.3, pAP beta-glucoside: 56%, pNP beta-glucoside: 127% activity compared to wild-type
A419W
-
furcatin: 26%, pNP beta-primeveroside: 24% and kcat/Km (min-1 * mM-1) = 0.59, pAP beta-glucoside: 43%, pNP beta-glucoside: 39% activity compared to wild-type
E501A
-
furcatin: 0.1% activity compared to wild-type
E501D
-
furcatin: 0.2% activity compared to wild-type
E501L
-
furcatin: 0.1% activity compared to wild-type
E501Q
-
furcatin: 0.1% activity compared to wild-type
S504A
-
furcatin: 113%, pNP beta-primeveroside: 62% and kcat/Km (min-1 * mM-1) = 0.75, pAP beta-glucoside: 87%, pNP beta-glucoside: 87% activity compared to wild-type
S504W
-
furcatin: 1.4%, pNP beta-primeveroside: 1.3% and kcat/Km (min-1 * mM-1) = 0.013, pAP beta-glucoside: 20%, pNP beta-glucoside: 28% activity compared to wild-type