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Information on EC 3.2.1.147 - thioglucosidase
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EC Tree
3.2.1.147 thioglucosidaseIUBMB Comments
Has a wide specificity for thioglycosides.
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Word Map
- 3.2.1.147
- glucosinolates
- isothiocyanate
- brassica
- broccoli
- brassicaceae
- sulforaphane
-
cruciferous
-
nitril
- glucoraphanin
- mustard
- sprout
- oleracea
-
herbivore
- napus
-
cook
-
chemopreventive
- sinapis
- cabbage
- radish
- juncea
-
crucifer
-
epithiospecifier
-
anticarcinogenic
- italica
- brassicales
-
3.2.3.1
- glucotropaeolin
-
generalist
-
armoraciae
- rusticana
- watercress
-
bomb
- floret
- idioblasts
-
cyclocondensation
- kale
- abyssinica
- glucobrassicin
-
4-hydroxybenzyl
- raphanus
- analysis
- pharmacology
-
tuscan
- gluconasturtiin
- erucin
-
mercapturic
-
brussels
- nutrition
- agriculture
- moringa
- lepidium
-
pungen
- crambe
-
blanch
- biotechnology
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
myrosinase, myrosin, thioglucosidase, myrosinase a, thioglucoside glucohydrolase, cptgg1, myr ii, myr1.bn1, myrii, atypical myrosinase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AtBGLU37
AtBGLU38
atypical myrosinase
beta-glucosidase 26, peroxisomal
beta-glucosidase 37
beta-glucosidase 38
beta-thioglucosidase
beta-thioglucosidase glucohydrolase
beta-thioglucoside glucohydrolase
BGLU26
EC 3.2.3.1
glucosidase, thio-
-
-
-
-
glucosinolase
-
-
-
-
MYR
myrosin
-
-
-
-
myrosinase
PEN2
sinigrase
-
-
-
-
sinigrinase
sinigrinase 1
sinigrinase 2
TGG1
TGG2
Thioglucosidase
-
-
-
-
thioglucoside glucohydrolase
thioglycosidase
beta-thioglucosidase
-
-
-
-
beta-thioglucoside glucohydrolase
-
-
-
-
EC 3.2.3.1
-
-
formerly
-
myrosinase
-
-
-
-
myrosinase
-
-
sinigrinase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a thioglucoside + H2O = a sugar + a thiol
the mechanism involves a first step acid-base catalyzed reaction with the formation of the glycosyl enzyme intermediate and the benzyl isothiocyanate obtained by the enzyme-independent Lossen rearrangement of the transient thiohydroximate-O-sulfonate, a sulfate anion and a proton are also released
-
a thioglucoside + H2O = a sugar + a thiol
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of O-beta-glucosyl bond
-
-
-
-
hydrolysis of O-glycosyl bond
-
-
-
-
hydrolysis of S-glycosyl bond
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
thioglucoside glucohydrolase
Has a wide specificity for thioglycosides.
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CAS REGISTRY NUMBER
COMMENTARY
9025-38-1
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-2-hydroxy-3-butenyl glucosinolate + H2O
D-glucose +
-
i.e. epi-progoitrin
presence of endogenous epithiospecifier protein directs the reaction toward formation of an epithionitrile
-
?
(R)-4-methylsulfinylbutyl glucosinolate + H2O
?
-
i.e. glucoraphanin or GRP
-
-
?
1-methoxyindol-3-ylmethyl-glucosinolate + H2O
1-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
2-(4-hydroxyphenyl)ethylglucosinolate + H2O
D-glucose + 4-(2-carboxy-1-hydroxyethyl)phenyl sulfate
-
-
-
-
?
2-(4-methoxyphenyl)ethylglucosinolate + H2O
D-glucose + 4-(2-cyano-1-hydroxyethyl)phenyl sulfate + 4-(2-cyanoethyl)phenyl sulfate
-
-
-
-
?
2-hydroxy-3-butenylglucosinolate + H2O
5-vinyl-2-oxazolidine thione + D-glucose
-
-
-
-
?
2-nitrophenyl beta-D-glucopyranoside + H2O
2-nitrophenol + D-glucopyranose
-
-
-
?
2-phenylethylglucosinolate + H2O
2-phenylethyl-isothiocyanate + D-glucose
-
-
-
-
?
2-propenylglucosinolate + H2O
2-propenyl-isothiocyanate + D-glucose
-
epithiospecifier protein and nitrile-specifier protein can switch myrosinase-catalyzed degradation of 2-propenylglucosinolate from isothiocyanate to nitrile, only epithiospecifier protein generates the corresponding epithionitrile
-
-
?
3-benzyloxypropylglucosinolate + H2O
3-benzyloxypropyl-isothiocyanate + D-glucose
-
-
-
-
?
3-butenylglucosinolate + H2O
3-butenyl-isothiocyanate + D-glucose
-
-
-
-
?
3-methylthiopropylglucosinolate + H2O
3-methylthiopropyl-isothiocyanate + D-glucose
-
-
-
-
?
4-(methylsulfinyl)butyl glucosinolate + H2O
D-glucose + ?
-
i.e. glucoraphanin
presence of endogenous epithiospecifier protein directs the reaction toward formation of sulforaphane nitrile in place of the anticancerogenic sulforaphane
-
?
4-benzyloxybutylglucosinolate + H2O
4-benzyloxybutyl-isothiocyanate + D-glucose
-
-
-
-
?
4-hydroxybenzyl glucosinolate + H2O
4-hydroxybenzyl isothiocyanate + D-glucose
-
-
-
-
?
4-hydroxybenzylglucosinolate + H2O
D-glucose + 4-hydroxyphenylacetamide sulfate + ?
-
-
-
-
?
4-hydroxybenzylglucosinolate + H2O
D-glucose + 4-hydroxyphenylacetonitrile sulfate + ?
-
-
-
-
?
4-methoxyindol-3-ylmethyl-glucosinolate + H2O
4-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
4-methylsulfinylbutyl glucosinolate + H2O
4-methylsulfinylbutyl isothiocyanate + D-glucose
-
isolated from seeds of Sinapis alba
-
-
?
4-methylsulfinylbutylglucosinolate + H2O
4-methylsulfinylbutyl-isothiocyanate + D-glucose
-
-
-
-
?
4-methylthiobutylglucosinolate + H2O
4-methylthiobutyl-isothiocyanate + D-glucose
-
-
-
-
?
4-methylumbelliferyl-beta-D-glucoside + H2O
4-methylumbelliferone + D-glucose
-
-
-
-
?
4-nitrophenyl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranoside + H2O
4-nitrobenzenethiol + N-acetyl-D-glucosamine
4-pentenylglucosinolate + H2O
4-pentenyl-isothiocyanate + D-glucose
-
-
-
-
?
5-methylthiopentylglucosinolate + H2O
5-methylthiopentyl-isothiocyanate + D-glucose
-
-
-
-
?
6-methylthiohexylglucosinolate + H2O
6-methylthiohexyl-isothiocyanate + D-glucose
-
-
-
-
?
7-methylthioheptylglucosinolate + H2O
7-methylthioheptyl-isothiocyanate + D-glucose
-
-
-
-
?
8-methylthiooctylglucosinolate + H2O
8-methylthiooctyl-isothiocyanate + D-glucose
-
-
-
-
?
allylglucosinolate + H2O
?
-
-
in presence of epithionitrile from Arabidopsis thaliana, formation of epithionitrile and nitrile. In presence of nitrile specifier protein from Pieris rapa, formation of nitrile
-
?
benzylglucosinolate + H2O
benzylisothiocyanate + D-glucose + ?
-
nitrile-specifier proteins, especially nitrile-specifier protein 2, NSP2, in conjunction with myrosinase enable the enzyme to generate nitriles, overview
-
-
?
glucoraphenin + H2O
?
-
3.8% of the activity with epi-progoitrin
-
-
?
glucosinolate + H2O
isothiocyanate + thiocyanate + nitrile + epithionitrile + ?
-
-
-
-
?
indol-3-ylmethyl glucosinolate + H2O
indo-3-ylmethyl isothiocyanate + D-glucose
-
high activity
-
-
?
indolyl-3-methylglucosinolate + H2O
indolyl-3-methyl-isothiocyanate + D-glucose
-
-
-
-
?
p-nitrophenyl beta-D-glucopyranoside + H2O
p-nitrophenol + D-glucose
-
-
-
-
?
progoitrin + H2O
(1E,3S)-3-hydroxy-n-(sulfooxy)pent-4-enimidothioic acid + D-glucose
-
-
-
-
?
(2R)-2-hydroxy-2-phenylethylglucosinolate + H2O
D-glucose + ?
-
i.e. glucosibarin
-
-
?
(2R)-2-hydroxy-2-phenylethylglucosinolate + H2O
D-glucose + ?
-
i.e. glucosibarin
-
-
?
1-methoxyindol-3-ylmethyl-glucosinolate + H2O
1-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
-
-
-
?
1-methoxyindol-3-ylmethyl-glucosinolate + H2O
1-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
-
-
-
?
4-methoxyindol-3-ylmethyl-glucosinolate + H2O
4-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
-
-
-
?
4-methoxyindol-3-ylmethyl-glucosinolate + H2O
4-methoxyindol-3-ylmethyl isothiocyanate + D-glucose
-
-
-
?
4-methylsulfinylbutylglucosinolate + H2O
?
-
-
in presence of epithionitrile from Arabidopsis thaliana, formation of epithionitrile and nitrile. In presence of nitrile specifier protein from Pieris rapa, formation of nitrile
-
?
4-methylthiobutylglucosinolate + H2O
?
-
-
in presence of epithionitrile from Arabidopsis thaliana, formation of epithionitrile and nitrile. In presence of nitrile specifier protein from Pieris rapa, formation of nitrile
-
?
4-nitrophenyl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranoside + H2O
4-nitrobenzenethiol + N-acetyl-D-glucosamine
-
-
-
-
?
4-nitrophenyl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranoside + H2O
4-nitrobenzenethiol + N-acetyl-D-glucosamine
-
-
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + beta-D-glucopyranose
-
-
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + beta-D-glucopyranose
-
-
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
-
-
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
a poor substrate for ArMy2
-
-
?
4-nitrophenyl beta-D-glucopyranoside + H2O
4-nitrophenol + D-glucopyranose
-
-
-
?
a thioglucos