Information on EC 3.2.1.126 - coniferin beta-glucosidase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY
3.2.1.126
-
RECOMMENDED NAME
GeneOntology No.
coniferin beta-glucosidase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
coniferin + H2O = D-glucose + coniferol
show the reaction diagram
-
-
-
-
coniferin + H2O = D-glucose + coniferol
show the reaction diagram
mechanism
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of O-glycosyl bond
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
coniferin metabolism
-
-
Phenylpropanoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
coniferin beta-D-glucosidase
Also hydrolyses syringin, 4-cinnamyl alcohol beta-glucoside and, more slowly, some other aryl beta-glycosides. A plant cell-wall enzyme involved in the biosynthesis of lignin.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
beta-glucosidase
-
-
coniferin-hydrolyzing beta-glucosidase
-
-
-
-
glucosidase, coniferin beta-
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
83869-30-1
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ecotype Columbia
-
-
Manually annotated by BRENDA team
chickpea
-
-
Manually annotated by BRENDA team
spruce
-
-
Manually annotated by BRENDA team
var. latifolia Engelm, 10-15 years old
-
-
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
?
show the reaction diagram
-
-
-
-
?
2-nitrophenyl beta-D-galactoside + H2O
2-nitrophenol + D-galactose
show the reaction diagram
-
-
-
-
-
2-nitrophenyl beta-D-galactoside + H2O
2-nitrophenol + D-galactose
show the reaction diagram
-
reaction at 16% (isozyme I) or 13% (isozyme II) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
2-nitrophenyl beta-D-glucoside + H2O
2-nitrophenol + D-glucose
show the reaction diagram
-
-
-
-
-
2-nitrophenyl beta-D-glucoside + H2O
2-nitrophenol + D-glucose
show the reaction diagram
-
best substrate
-
-
-
2-nitrophenyl beta-D-glucoside + H2O
2-nitrophenol + beta-D-glucose
show the reaction diagram
-
57% of the activity with coniferin
-
?
2-nitrophenyl beta-D-xyloside + H2O
2-nitrophenol + D-xylose
show the reaction diagram
-
poor substrate
-
-
-
4-coumaryl beta-D-glucoside + H2O
coumaric acid + D-glucose
show the reaction diagram
-
reaction at 25% (isozyme II) or 4% (isozyme I) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
4-methylumbelliferyl beta-D-glucosaminide + H2O
4-methylumbelliferone + D-glucosamine
show the reaction diagram
-
poor substrate
-
-
-
4-methylumbelliferyl beta-D-glucoside + H2O
4-methylumbelliferone + D-glucose
show the reaction diagram
-
-
-
-
-
4-methylumbelliferyl beta-D-glucoside + H2O
4-methylumbelliferone + D-glucose
show the reaction diagram
-
reaction at 79% (isozyme II) or 51% (isozyme I) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
4-methylumbelliferyl beta-D-glucoside + H2O
4-methylumbelliferone + beta-D-glucose
show the reaction diagram
-
16% of the activity with coniferin
-
?
4-methylumbelliferyl-beta-D-glucoside
4-methylumbelliferol + beta-D-glucose
show the reaction diagram
-
9% activity with BGLU46
-
-
?
4-nitrophenyl beta-D-galactoside + H2O
4-nitrophenol + D-galactose
show the reaction diagram
-
-
-
-
-
4-nitrophenyl beta-D-galactoside + H2O
4-nitrophenol + D-galactose
show the reaction diagram
-
poor substrate, not
-
-
-
4-nitrophenyl beta-D-glucoside + H2O
4-nitrophenol + D-glucose
show the reaction diagram
-
-
-
-
-
4-nitrophenyl beta-D-glucoside + H2O
4-nitrophenol + D-glucose
show the reaction diagram
-
reaction at 56% (isozyme II) or 8% (isozyme I) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
4-nitrophenyl beta-D-glucoside + H2O
4-nitrophenol + beta-D-glucose
show the reaction diagram
-
26% of the activity with coniferin
-
?
5-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenylmethylene]-2-thioxothiazolidin-4-one-3-ethanoic acid + H2O
?
show the reaction diagram
-
synthetic coniferin analog, 45% of the activity with coniferin
-
?
arbutin
benzene-1,4-diol + beta-D-glucose
show the reaction diagram
-
6% activity with BGLU46
-
-
?
arbutin + H2O
?
show the reaction diagram
-
-
-
?
coniferin
beta-D-glucose + coniferyl aldehyde
show the reaction diagram
-
87% activity with BGLU45 and 8% activity with BGLU46
-
-
?
coniferin + H2O
coniferol + D-glucose
show the reaction diagram
-
-
-
-
-
coniferin + H2O
coniferol + D-glucose
show the reaction diagram
-
-
-
-
coniferin + H2O
coniferol + D-glucose
show the reaction diagram
-
reaction at 52% (isozyme I) or 38% (isozyme II) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
coniferin + H2O
coniferol + D-glucose
show the reaction diagram
-
i.e. coniferyl alcohol beta-D-glucoside, (E)-coniferin
i.e. trans-coniferyl alcohol
-
coniferin + H2O
D-glucose + coniferol
show the reaction diagram
-
natural substrate, 20000fold preference for the natural substrate coniferin over cellobiose
-
?
coniferin + H2O
D-glucose + coniferol
show the reaction diagram
-
the native substrate is efficiently hydrolyzed, preferred substrates, native substrate, may play a crucial role in stem lignification
-
?
coniferin + H2O
?
show the reaction diagram
-
plant cell wall enzyme, involved in lignin biosynthesis
-
-
-
ferulic acid p-beta-glucoside + H2O
ferulic acid + D-glucose
show the reaction diagram
-
-
-
-
-
o-nitrophenyl beta-D-glucopyranoside + H2O
beta-D-glucose + o-nitrophenol
show the reaction diagram
-
-
-
?
o-nitrophenyl-beta-D-glucopyranoside
o-nitrophenol + beta-D-glucose
show the reaction diagram
-
most rapidly hydrolysed by BGLU45 and BGLU46 with relative rates of 619% and 449%, respectively, of the rate of p-nitrophenyl-beta-D-glucoside degradation
-
-
-
p-coumaryl beta-D-glucoside
p-coumaric acid + beta-D-glucose
show the reaction diagram
-
6.9% activity with BGLU45 and 71% activity with BGLU46
-
-
?
p-nitrophenyl alpha-L-arabinofuranoside + H2O
p-nitrophenol + alpha-L-arabinofuranose
show the reaction diagram
-
with moderate efficiency
-
?
p-nitrophenyl beta-cellobioside + H2O
?
show the reaction diagram
-
releases only terminal glucose from the substrate
-
?
p-nitrophenyl beta-D-fucopyranoside + H2O
beta-D-fucose + p-nitrophenol
show the reaction diagram
-
with moderate efficiency
-
?
p-nitrophenyl beta-D-galactopyranoside + H2O
beta-D-galactose + p-nitrophenol
show the reaction diagram
-
with low efficiency
-
?
p-nitrophenyl beta-D-glucopyranoside + H2O
beta-D-glucose + p-nitrophenol
show the reaction diagram
-
-
-
?
p-nitrophenyl beta-D-xylopyranoside + H2O
beta-D-xylose + p-nitrophenol
show the reaction diagram
-
73% of the efficiency with p-nitrophenyl beta-D-glucopyranoside
-
?
p-nitrophenyl-beta-D-galactopyranoside
p-nitrophenol + beta-D-galactose
show the reaction diagram
-
0.4% activity with BGLU45 and 21% activity with BGLU46
-
-
-
p-nitrophenyl-beta-D-glucopyranoside
p-nitrophenol + beta-D-glucose
show the reaction diagram
-
100% activity with BGLU45 and BGLU46
-
-
-
phenyl-beta-D-glucoside
phenol + beta-D-glucose
show the reaction diagram
-
62% activity with BGLU46
-
-
?
picein + H2O
?
show the reaction diagram
-
-
-
-
-
picein + H2O
?
show the reaction diagram
-
reaction at 50% (isozyme II) or 12% (isozyme I) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
salicin
beta-D-glucose + salicyl alcohol
show the reaction diagram
-
100% activity with BGLU46
-
-
?
salicin + H2O
?
show the reaction diagram
-
-
-
?
salicin + H2O
?
show the reaction diagram
-
poor substrate
-
-
-
salicin + H2O
?
show the reaction diagram
-
reaction at 25% (isozyme II) or 2% (isozyme I) the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
syringin
beta-D-glucose + sinapyl alcohol
show the reaction diagram
-
100% activity with BGLU45 and 6% activity with BGLU46
-
-
?
syringin + H2O
?
show the reaction diagram
-
poor substrate
-
-
-
syringin + H2O
?
show the reaction diagram
-
reaction at about 30% the rate of 2-nitrophenyl beta-D-glucoside hydrolysis
-
-
-
syringin + H2O
?
show the reaction diagram
-
51% of the activity with coniferin
-
?
feruloyl glucoside + H2O
ferulic acid + glucose
show the reaction diagram
-
poor substrate
-
-
-
additional information
?
-
-
very poor substrates are arbutin or indican, no substrates are alpha-glucosides, 4-methylumbelliferyl beta-cellobioside, 4-methylumbelliferyl beta-glucuronide, quercetin 3-rhamnosyl glucoside, quercetin 3-rhamnoside or cellobiose
-
-
-
additional information
?
-
-
enzyme has a high transglycosylation activity in the presence of alcohols, transglycosylation mechanism
-
?
additional information
?
-
-
not: disaccharide-containing glycoside, 4-nitrophenyl beta-cellobioside, 4-methylumbelliferyl alpha-glucoside
-
?
additional information
?
-
-
no activity with sinigrin, methyl-beta-D-glucoside, D(+)cellobiose, beta-gentiobiose, D(+)maltose, sucrose, p-nitrophenyl-1-thio-beta-D-glucopyranoside, p-nitrophenyl-alpha-D-glucopyranoside, p-nitrophenyl-N-acetyl-beta-D-glucosaminide, p-nitrophenyl-beta-D-mannopyranoside, p-nitrophenyl-beta-D-xylopyranoside, p-nitrophenyl-beta-L-fucopyranoside and p-nitrophenyl-beta-L-arabinopyranoside
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
coniferin + H2O
D-glucose + coniferol
show the reaction diagram
-
natural substrate
-
?
coniferin + H2O
D-glucose + coniferol
show the reaction diagram
-
native substrate, may play a crucial role in stem lignification
-
?
coniferin + H2O
?
show the reaction diagram
-
plant cell wall enzyme, involved in lignin biosynthesis
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
D-glucose
-
competitive inhibitor, p-nitrophenyl beta-D-glucopyranoside as substrate
deoxynojirimycin
-
strong, competitive inhibitor, p-nitrophenyl beta-D-glucopyranoside as substrate
glucono-1,5-lactone
-
-
glucuronolactone
-
strong, competitive inhibitor, p-nitrophenyl beta-D-glucopyranoside as substrate
isopropyl 1-thio-beta-D-glucopyranoside
-
competitive inhibitor, p-nitrophenyl beta-D-glucopyranoside as substrate
additional information
-
not inhibited by 24 mM xylose
-
additional information
-
not inhibited by bromoconduritol or conduritol B epoxide
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-butanol
-
20 mM, activates due to transglycosylation activity with over 80% of p-nitrophenyl beta-D-glucopyranoside being converted to 1-butyl beta-D-glucopyranoside in the presence of Cbg1 and 100 mM 1-butanol
1-Heptanol
-
20 mM, activates
1-Hexanol
-
20 mM, activates
1-Octanol
-
20 mM, activates
1-Pentanol
-
20 mM, activates
1-propanol
-
20 mM, activates, highest rate of consumption of p-nitrophenyl beta-D-glucopyranoside in the presence of 0.6 M 1-propanol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
3
2-nitrophenyl beta-D-galactoside
-
-
0.9
4-Methylumbelliferyl beta-D-glucosaminide
-
-
0.4
4-methylumbelliferyl beta-D-glucoside
-
ferulic acid p-beta-glucoside, 4-nitrophenyl beta-D-glucoside
1
4-methylumbelliferyl beta-D-glucoside
-
hypocotyls
2.3
4-methylumbelliferyl beta-D-glucoside
-
pH 5.5, 30C
0.7
4-nitrophenyl beta-D-glucoside
-
hypocotyls
1.9
4-nitrophenyl beta-D-glucoside
-
pH 5.5, 30C
0.021
Arbutin
-
pH 6.5, 30C
0.023
coniferin
-
pH 6.5, 30C
0.18
coniferin
-
pH 5.5, 30C
0.38
coniferin
-
roots
0.8
coniferin
-
-
1.3
coniferin
-
hypocotyls
7
coniferin
-
BGLU45
0.06
o-nitrophenyl beta-D-glucopyranoside
-
pH 6.5, 30C
2.2
p-coumaryl beta-D-glucoside
-
BGLU46
0.27
p-nitrophenyl alpha-L-arabinofuranoside
-
pH 6.5, 30C
0.08
p-nitrophenyl beta-D-fucopyranoside
-
pH 6.5, 30C
4
p-nitrophenyl beta-D-galactopyranoside
-
pH 6.5, 30C
0.012
p-nitrophenyl beta-D-glucopyranoside
-
pH 6.5, 30C
0.005
p-nitrophenyl beta-D-xylopyranoside
-
pH 6.5, 30C
0.6
Picein
-
-
0.6
Picein
-
2-nitrophenyl beta-D-glucoside, 2-nitrophenyl beta-D-galactoside, hypocotyls
6.3
Picein
-
hypocotyls
0.045
Salicin
-
pH 6.5, 30C
0.29
syringin
-
pH 5.5, 30C
1.8
syringin
-
hypocotyls
5
syringin
-
4-nitrophenyl beta-D-glucoside
5.1
syringin
-
BGLU45
0.3
formononetin 7-beta-glucoside
-
2-nitrophenyl beta-glucoside
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
155
o-nitrophenyl beta-D-glucopyranoside
-
pH 6.5, 30C
118
p-nitrophenyl alpha-L-arabinofuranoside
-
pH 6.5, 30C
22.1
p-nitrophenyl beta-D-fucopyranoside
-
pH 6.5, 30C
46.6
p-nitrophenyl beta-D-galactopyranoside
-
pH 6.5, 30C
3.2
p-nitrophenyl beta-D-glucopyranoside
-
pH 6.5, 30C
95.4
p-nitrophenyl beta-D-glucopyranoside
-
pH 6.5, 30C
28.9
p-nitrophenyl beta-D-xylopyranoside
-
pH 6.5, 30C
3.15
Salicin
-
pH 6.5, 30C
86.7
Salicin
-
pH 6.5, 30C
106
coniferin
-
pH 6.5, 30C
additional information
additional information
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2.9
D-glucose
-
pH 6.5, 30C
0.00078
deoxynojirimycin
-
pH 6.5, 30C
0.0039
glucuronolactone
-
pH 6.5, 30C
5.6
isopropyl 1-thio-beta-D-glucopyranoside
-
pH 6.5, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.1
-
BGLU45, crude extract
4.5
-
hypocotyls
6.6
-
pH 5.5, 30C
35.9
-
BGLU45, purified enzyme
39 - 41
-
pH 6.5, 30C
43.8
-
BGLU46, crude extract
599
-
BGLU46, purified enzyme
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5 - 5.5
-
hypocotyls
5.4 - 5.9
-
optimum in the range at 30C
additional information
-
pI: 10 (isozyme I), pI: 10.3 (isozyme II)
additional information
-
pI: 3.8
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3.5 - 6.5
-
about half-maximal activity at pH 3.5 and 6.5, hypocotyls
4 - 7.5
-
about 20% of maximal activity at pH 4 and 7.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
assay at
30
-
assay at
30
-
assay at
30
-
assay at
40 - 45
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5
-
isoelectric focusing, pH gradient 4-7
4.5
-
chromatofocussing, pH gradient of 5.5 to 4
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
tissue distribution
Manually annotated by BRENDA team
-
BGLU45 and BGLU46 display increasing levels of expression from apex to base, matching the known increase in lignification
Manually annotated by BRENDA team
-
lignifying
Manually annotated by BRENDA team
-
exclusive presence in the differentiating xylem
Manually annotated by BRENDA team
additional information
-
BGLU45 and BGLU46 absent from rosette leaves or flowers
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
58570
-
Picea abies, sedimentation equilibrium method
26043
60000
-
gel filtration, native PAGE
653495
90000
-
Pinus banksiana, 2 isozymes, MW 90000 and 110000
26044
110000
-
Cicer arietinum, gel filtration
26041
110000
-
Pinus banksiana, 2 isozymes, MW 90000 and 110000
26044
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 98000, about, SDS-PAGE, x * 88289, sequence calculation
dimer
-
2 * 28000, SDS-PAGE
dimer
-
1 * 43000 + 1 * 63000, Cicer arietinum, SDS-PAGE
monomer
-
1 * 57000, Picea abies, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
-
-
glycoprotein
-
-
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
0.5 M NaCl stabilizes, removal inactivates
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, in the presence of 0.5 M NaCl, several months
-
-20C, crude cell wall preparation, frozen with liquid nitrogen, at least 3 months
-
4C, in 0.025 M McIlvaine buffer, pH 5, 0.1 M NaCl, 0.02% NaN3, less than 10% loss of activity within 15 days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant Cbg1
-
to apparent homogeneity by ammonium sulfate fractionation and hydrophobic interaction chromatography, BGLU45 8.8fold and BGLU46 13.7fold purified
-
to near homogeneity
-
hypocotyls
-
2 isozymes
-
2760fold
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
-
cDNAs encoding BGLU45 and BGLU46 expressed in Pichia pastoris
-