3.2.1.149: beta-primeverosidase
This is an abbreviated version!
For detailed information about beta-primeverosidase, go to the full flat file.
Word Map on EC 3.2.1.149
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3.2.1.149
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beta-d-galactosidase
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alpha-d-mannosidase
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beta-d-glucuronidase
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glycosidases
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alpha-d-glucosidase
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alpha-l-fucosidase
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beta-d-glucoside
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beta-d-fucosidase
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alpha-d-galactosidase
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3.2.1.21
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beta-d-xylosidase
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n-acetyl-beta-d-glucosaminidase
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almond
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p-nitrophenyl-beta-d-glucopyranoside
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alpha-l-arabinosidase
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gentiobiose
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beta-d-n-acetylglucosaminidase
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emulsin
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beta-d-xylopyranoside
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n-acetyl-beta-d-galactosaminidase
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nutrition
- 3.2.1.149
- beta-d-galactosidase
- alpha-d-mannosidase
- beta-d-glucuronidase
- glycosidases
- alpha-d-glucosidase
- alpha-l-fucosidase
- beta-d-glucoside
- beta-d-fucosidase
- alpha-d-galactosidase
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3.2.1.21
- beta-d-xylosidase
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n-acetyl-beta-d-glucosaminidase
- almond
- p-nitrophenyl-beta-d-glucopyranoside
- alpha-l-arabinosidase
- gentiobiose
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beta-d-n-acetylglucosaminidase
- emulsin
- beta-d-xylopyranoside
- n-acetyl-beta-d-galactosaminidase
- nutrition
Reaction
Synonyms
4-methylumbelliferyl-beta-D-glucopyranoside:beta-glucosidase, arbutinase, ary beta-glucosidase, beta-D-glucosidase, beta-D-glucoside glucohydrolase, beta-glucosidase, beta-glucoside hydrolase, beta-primeverosidase, diglycoside-specific beta-primeverosidase, p-nitrophenyl beta-glucosidase, primeverosidase, vicianase
ECTree
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Substrates Products
Substrates Products on EC 3.2.1.149 - beta-primeverosidase
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REACTION DIAGRAM
(R)-1-phenylethyl beta-D-glucopyranoside + H2O
(R)-1-phenylethanol + beta-D-glucopyranose
LC-MS analysis and quantitative GC-MS analysis of substrate and product
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-
?
(R)-1-phenylethyl beta-primeveroside + H2O
(R)-1-phenylethanol + beta-primeverose
LC-MS analysis and quantitative GC-MS analysis of substrate and product
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-
?
(R)-linalyl beta-vicianoside + H2O
linalol + 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside
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-
-
?
(S)-1-phenylethyl beta-D-glucopyranoside + H2O
(S)-1-phenylethanol + beta-D-glucopyranose
LC-MS analysis and quantitative GC-MS analysis of substrate and product
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-
?
(S)-1-phenylethyl beta-primeveroside + H2O
(S)-1-phenylethanol + beta-primeverose
LC-MS analysis and quantitative GC-MS analysis of substrate and product
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-
?
2-phenylethyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
2-phenylethyl 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside + H2O
2-phenylethyl 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranose + 2-phenylethanol
pH 6.0, 37°C, 0.05% activity
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-
?
2-phenylethyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside + H2O
beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose + 2-phenylethanol
pH 6.0, 37°C, 0.60% activity
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-
?
2-phenylethyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
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trivial name beta-primeveroside
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-
?
2-phenylethyl beta-acuminoside + H2O
2-phenylethanol + 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside
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i.e. 2-phenylethyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside
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?
2-phenylethyl beta-D-glucopyranoside + H2O
2-phenylethanol + beta-D-glucopyranose
low activity
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-
?
2-phenylethyl beta-D-glucopyranoside + H2O
2-phenylethanol + D-glucopyranose
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-
-
-
?
2-phenylethyl beta-gentiobioside + H2O
gentiobiose + 2-phenylethanol
pH 6.0, 37°C, 0.34% activity
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-
?
2-phenylethyl beta-primeveroside + H2O
2-phenylethanol + beta-primeverose
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-
-
?
2-phenylethyl beta-vicianoside + H2O
2-phenylethanol + 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside
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-
-
?
2-phenylethyl beta-vicianoside + H2O
vicianose + 2-phenylethanol
pH 6.0, 37°C, 2.97% activity
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-
?
2-phenylethyl-6-O-alpha-D-arabinosyl-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-alpha-D-arabinosyl-beta-D-glucopyranoside
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trivial name beta-vicianoside, 3% of activity with 2-phenyl-beta-primeveroside
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-
?
2-phenylethyl-6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside
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trivial name beta-vicianoside, 0.8% of activity with 2-phenyl-beta-primeveroside
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?
2-phenylethyl-6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
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trivial name beta-vicianoside, 0.25% of activity with 2-phenyl-beta-primeveroside
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?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
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-
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?
4-nitrophenyl beta-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
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pH 5.5, 40°C, 15% hydrolysis
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-
?
4-nitrophenyl beta-primeveroside + H2O
4-nitrophenol + primeverose
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i.e. 4-nitrophenyl-6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
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?
4-nitrophenyl-beta-primeveroside + H2O
4-nitrophenol + beta-primeverose
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-
-
?
6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside + H2O
alpha-L-arabinopyranose + beta-D-glucopyranose
hydrolyzed with lower activity
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-
?
6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside + H2O
beta-D-apiofuranose + beta-D-glucopyranose
hydrolyzed with lower activity
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-
?
6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
beta-D-xylopyranose + beta-D-glucopyranose
hydrolyzed with highest activity
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-
?
6-O-beta-L-arabinopyranosyl-beta-D-glucopyranoside + H2O
beta-D-arabinopyranose + beta-D-glucopyranose
hydrolyzed with lower activity
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-
?
a 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose + an alcohol
a beta-primeveroside + H2O
? + primeverose
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the enzyme shows broad substrate specificity with respect to the disaccharide glycon moiety (subsite-2), Thr271 and Thr415 play important roles in subsite-2 of the enzyme
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-
?
benzyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
benzyl alcohol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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i.e. 2-benzyl beta-D-primeveroside
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?
benzyl 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside + H2O
benzyl alcohol + 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside
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-
-
-
?
benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside + H2O
benzyl alcohol + beta-D-apiofuranosyl-(1->6)-D-glucose
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-
-
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?
geranyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
geraniol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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i.e. geranyl beta-D-primeveroside
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?
geranyl 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside + H2O
geraniol + 6-O-alpha-L-arabinofuranosyl-beta-D-glucopyranoside
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-
-
?
geranyl beta-primeveroside + H2O
geraniol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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-
?
linalyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
linalol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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-
-
?
linalyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
linalool + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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-
-
?
p-nitrophenol beta-D-glucopyranoside + H2O
D-glucose + p-nitrophenol
pH 6.0, 37°C, 0.23% activity
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?
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
p-nitrophenol + 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
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trivial name beta-primeveroside
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-
?
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
primeverose + p-nitrophenol
p-nitrophenyl beta-D-glucoside + H2O
p-nitrophenol + D-glucose
pH 6.0, 37°C, 0.5% activity (purified from tea), 0.3% activity (recombinant enzyme)
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?
p-nitrophenyl beta-gentiobioside + H2O
p-nitrophenol + D-gentiobiose
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pH 5.5, 40°C, 2.5% hydrolysis
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?
p-nitrophenyl beta-gentiobioside + H2O
p-nitrophenol + gentiobiose
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37°C, 41% hydrolysis
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?
p-nitrophenyl-beta-D-glucopyranoside + H2O
4-nitrophenol + beta-D-glucose
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?
p-nitrophenyl-beta-D-glucopyranoside + H2O
p-nitrophenol + beta-D-glucose
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-
-
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?
(Z)-3-hexenol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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?
(Z)-3-hexenyl beta-primeveroside + H2O
(Z)-3-hexenol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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?
2-phenylethanol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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i.e. 2-phenylethyl beta-D-primeveroside
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?
2-phenylethyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
2-phenylethanol + 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose
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i.e. 2-phenylethyl beta-D-primeveroside
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?
2-phenylethanol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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?
2-phenylethyl beta-primeveroside + H2O
2-phenylethanol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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?
primeverose + 2-phenylethanol
pH 6.0, 37°C
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-
?
2-phenylethyl beta-primeveroside + H2O
primeverose + 2-phenylethanol
pH 6.0, 37°C, 100% activity
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?
2-phenylethyl beta-primeveroside + H2O
primeverose + 2-phenylethanol
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pH 6.0, 37°C, 100% activity
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?
6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose + an alcohol
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?
a 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose + an alcohol
the enzyme hydrolyzes beta-primeveroside at the beta-glycosidic bond of primeverose to aglycone, and releases aromatic alcoholic volatiles of aglycones
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?
a 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside + H2O
6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranose + an alcohol
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-
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-
?
phenylmethanol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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-
?
benzyl beta-primeveroside + H2O
phenylmethanol + primeverose
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pH 5.5, 40°C, 0.1% hydrolysis
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-
?
eugenol + primeverose
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37°C, 1.8% hydrolysis
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?
eugenyl beta-primeveroside + H2O
eugenol + primeverose
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37°C, 1.8% hydrolysis
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-
?
eugenyl beta-primeveroside + H2O
eugenol + primeverose
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i.e. eugenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranose
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-
?
eugenyl beta-primeveroside + H2O
eugenol + primeverose
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pH 5.5, 40°C, 2.5% hydrolysis
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-
?
eugenyl beta-primeveroside + H2O
eugenol + primeverose
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pH 5.5, 40°C, 2.5% hydrolysis
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-
?
4-allyl-phenol + ?
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pH 5.5, 40°C, 1.0% hydrolysis
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-
?
furcatin + H2O
4-allyl-phenol + ?
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pH 5.5, 40°C, 1.0% hydrolysis
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-
?
primeverose + p-nitrophenol
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37°C, 100% hydrolysis
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?
p-nitrophenyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside + H2O
primeverose + p-nitrophenol
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37°C, 100% hydrolysis
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-
?
primeverose + p-nitrophenol
pH 6.0, 37°C
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-
?
p-nitrophenyl beta-primeveroside + H2O
primeverose + p-nitrophenol
pH 6.0, 37°C, 48% activity (purified from tea), 62% activity (recombinant enzyme)
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-
?
p-nitrophenyl beta-primeveroside + H2O
primeverose + p-nitrophenol
pH 6.0, 37°C, 54.4% activity
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-
?
p-nitrophenyl beta-primeveroside + H2O
primeverose + p-nitrophenol
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pH 5.5, 40°C, 100% hydrolysis
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?
?
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no activity with p-nitrophenol beta-D-xyloside and 2-phenylethyl beta-D-glucoside
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-
?
additional information
?
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no activity with p-nitrophenol beta-D-xyloside and 2-phenylethyl beta-D-glucoside
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?
additional information
?
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does not act on 2-phenylethyl beta-D-glucopyranoside
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?
additional information
?
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the enzyme only accepts primeverose as the glycone substrate, but broadly accepts various aglycones, including 2-phenylethanol, benzyl alcohol, linalool, and geraniol. Compared with aglycone-specific beta-glucosidases of the glycoside hydrolase family 1, beta-primeverosidase lacks the Trp crucial for aglycone recognition, and the resultant large cavity accepts aglycone and 6-O-beta-D-xylopyranosyl together. The enzyme barely hydrolyzes other beta-glycosides, in which the beta-1,6-Xyl group is absent or substituted by other sugars, such as monosaccharide glycosides (beta-D-glucopyranoside and beta-D-xylopyranoside, etc.) or other disaccharide glycosides, beta-vicianosides (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside), beta-gentiobiosides (6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside), and beta-acuminosides (6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside)
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?
additional information
?
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the diglycoside-specific enzyme beta-primeverosidase catalyses the hydrolysis of primeveroside into primeverose (a disaccharide of Xylbeta1-6Glc) and volatile aglycons
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?