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EC Tree
IUBMB Comments This enzyme, characterized from cruciferous plants, catalyses the last step in the biosynthesis of tryptophan- and phenylalanine-derived glucosinolates. cf. EC 2.8.2.38, aliphatic desulfoglucosinolate sulfotransferase.
The enzyme appears in viruses and cellular organisms
Synonyms
sot16, 3'-phosphoadenosine-5'-phosphosulfate:desulfoglucosinolate sulfotransferase, desulfoglucosinolate:paps sulfotransferase,
more
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3'-phosphoadenosine-5'-phosphosulfate:desulfoglucosinolate sulfotransferase
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desulfoglucosinolate:PAPS sulfotransferase
PAPS-desulfoglucosinolate sulfotransferase
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sulfotransferase, desulfoglucosinolate
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desulfoglucosinolate:PAPS sulfotransferase
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desulfoglucosinolate:PAPS sulfotransferase
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SOT16
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3'-phosphoadenylyl sulfate + desulfoglucotropeolin = adenosine 3',5'-bisphosphate + glucotropeolin
3'-phosphoadenylyl sulfate + indolylmethyl-desulfoglucosinolate = adenosine 3',5'-bisphosphate + glucobrassicin
(2)
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3'-phosphoadenylyl sulfate + desulfoglucotropeolin = adenosine 3',5'-bisphosphate + glucotropeolin
mechanism
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3'-phosphoadenylyl sulfate + desulfoglucotropeolin = adenosine 3',5'-bisphosphate + glucotropeolin
(1)
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sulfate group transfer
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3'-phosphoadenylyl-sulfate:aromatic desulfoglucosinolate sulfotransferase
This enzyme, characterized from cruciferous plants, catalyses the last step in the biosynthesis of tryptophan- and phenylalanine-derived glucosinolates. cf. EC 2.8.2.38, aliphatic desulfoglucosinolate sulfotransferase.
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3'-phosphoadenosine-5'-phosphosulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-p-hydroxy-benzylglucosinolate
adenosine 3',5'-bisphosphate + p-hydroxy-benzylglucosinolate
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-
-
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?
3'-phosphoadenylyl sulfate + desulfoallylglucosinolate
adenosine 3',5'-bisphosphate + allylglucosinolate
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-
-
-
?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
additional information
?
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3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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i.e. 3'-phosphoadenosine 5'phosphosulfate, i.e. PAPS
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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absolute specificity for desulfoglucosinolate structure
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?
3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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?
3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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?
additional information
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analysis/evaluation of desulfoglucosinolate:PAPS sulfotransferase from Arabidopsis thaliana ecotype Col-0 and myrosinase from Brevicoryne brassicae for the biosynthesis of benzyl isothiocyanate by the combined expression of the optimized enzymes in vitro, product identity is confirmed by gas chromatography/mass spectrometry analysis. SOTs from different Arabidopsis ecotypes show different efficiencies
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additional information
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analysis/evaluation of desulfoglucosinolate:PAPS sulfotransferase from Arabidopsis thaliana ecotype Col-0 and myrosinase from Brevicoryne brassicae for the biosynthesis of benzyl isothiocyanate by the combined expression of the optimized enzymes in vitro, product identity is confirmed by gas chromatography/mass spectrometry analysis. SOTs from different Arabidopsis ecotypes show different efficiencies
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additional information
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no activity with adenosine-5'-phosphosulfate as donor
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?
additional information
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involved in the biosynthesis of glucosinolates
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?
additional information
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involved with EC 2.4.1.195 in final steps of thioglycoside biosynthesis in cruciferous plants
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?
additional information
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involved with EC 2.4.1.195 in final steps of thioglycoside biosynthesis in cruciferous plants
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?
additional information
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no acceptors are quercetin, rutin, kaempferol, p-coumaric acid, ferulic acid, caffeic acid, phenylacetaldoxime
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?
additional information
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involved in the biosynthesis of glucosinolates
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?
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3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
additional information
?
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3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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?
3'-phosphoadenylylsulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
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?
additional information
?
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involved in the biosynthesis of glucosinolates
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?
additional information
?
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involved with EC 2.4.1.195 in final steps of thioglycoside biosynthesis in cruciferous plants
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?
additional information
?
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involved with EC 2.4.1.195 in final steps of thioglycoside biosynthesis in cruciferous plants
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?
additional information
?
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involved in the biosynthesis of glucosinolates
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?
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Mg2+
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slight activation
Mg2+
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51% activation at 10 mM
Mn2+
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23% activation at 1 mM, 10 mM inhibits by 53%
Mn2+
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23% activation at 1 mM, 10 mM inhibits by 53%
additional information
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no absolute requirement for cations
additional information
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not affected by FeCl3, FeCl2, CaCl2, CoCl2
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2,2'-dipyridyl
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26% inhibition at 10 mM
3'-phosphoadenosine-5'-phosphate
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adenosine-3',5'-bisphosphate
Ag+
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13% inhibition at 1 mM
Co2+
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at low concentration
DTNB
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2-mercaptoethanol protects
EDTA
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15% inhibition at 10 mM
Mn2+
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inhibitory at 10 mM, stimulating at 1 mM
N-ethylmaleimide
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2-mercaptoethanol protects
Ni2+
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30% inhibition at 1 mM
o-phenanthroline
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34% inhibition at 10 mM
p-chloromercuriphenylsulfonic acid
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2-mercaptoethanol protects
Pb(NO3)2
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25% inhibition at 1 mM
adenosine-3',5'-bisphosphate
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competitive to 3'-phosphoadenylylsulfate, kinetics
adenosine-3',5'-bisphosphate
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product inhibition
Cu2+
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at low concentration
Cu2+
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14% inhibition at 1 mM
iodoacetamide
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iodoacetamide
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weak inhibition
iodoacetic acid
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weak inhibition
iodoacetic acid
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weak inhibition
Zn2+
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at low concentration
Zn2+
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46% inhibition at 1 mM
additional information
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no inhibition by 3'-AMP, 5'-AMP, 2',5'-AMP, 3',5'-cAMP, 5'-ADP, 5'-ATP, adenosine-5'-phosphosulfate, benzaldoxime, phenylacetohydroximate, phenylacetothiohydroximate, S-methylphenylacetothiohydroximate, benzylglucosinolate
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additional information
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no inhibition by FeCl3, FeCl2, CaCl2, CoCl2
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0.05 - 0.1
3'-phosphoadenosine-5'-phosphosulfate
0.00078 - 0.06
3'-phosphoadenylylsulfate
0.67
desulfo-p-hydroxy-benzylglucosinolate
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pH 9.0, 30°C
0.0065
desulfoallylglucosinolate
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pH 9.0, 30°C
0.0023 - 0.1
desulfobenzylglucosinolate
additional information
additional information
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0.05
3'-phosphoadenosine-5'-phosphosulfate
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isoenzyme AtSOT18 Co10, pH 9.0, 37°C
0.1
3'-phosphoadenosine-5'-phosphosulfate
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isoenzyme AtSOT16 C24, pH 9.0, 37°C
0.1
3'-phosphoadenosine-5'-phosphosulfate
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isoenzyme AtSOT17 C24, pH 9.0, 37°C
0.00078
3'-phosphoadenylylsulfate
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pH 8.5-9.0, 30°C
0.06
3'-phosphoadenylylsulfate
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pH 9.0, 30°C
0.0023
desulfobenzylglucosinolate
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pH 8.5-9.0, 30°C
0.025
desulfobenzylglucosinolate
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isoenzyme AtSOT17 C24, pH 9.0, 37°C
0.035
desulfobenzylglucosinolate
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isoenzyme AtSOT18 C24, pH 9.0, 37°C
0.06
desulfobenzylglucosinolate
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isoenzyme AtSOT18 Co10, pH 9.0, 37°C
0.082
desulfobenzylglucosinolate
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pH 9.0, 30°C
0.1
desulfobenzylglucosinolate
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isoenzyme AtSOT16 C24, pH 9.0, 37°C
additional information
additional information
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kinetic studies
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additional information
additional information
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not detectable: 3'-phosphoadenosine-5'-phosphosulfate, isoenzyme AtSOT18 C24, pH 9.0, 37°C
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0.0004
adenosine-3',5'-bisphosphate
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pH 8.5-9.0, 30°C
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0.0000329
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partially purified enzyme
additional information
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0.0016197 Vmax desulfobenzylglucosinolate, isoenzyme AtSOT18 C24, pH 9.0, 37°C
additional information
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0.007499 Vmax 3'-phosphoadenosine-5'-phosphosulfate, isoenzyme AtSOT17 C24, pH 9.0, 37°C
additional information
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0.008518 Vmax desulfobenzylglucosinolate, isoenzyme AtSOT17 C24, pH 9.0, 37°C
additional information
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0.01026 Vmax 3'-phosphoadenosine-5'-phosphosulfate, isoenzyme AtSOT18 C24, pH 9.0, 37°C
additional information
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0.0415 Vmax desulfobenzylglucosinolate, isoenzyme AtSOT16 C24, pH 9.0, 37°C
additional information
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0.05105 Vmax 3'-phosphoadenosine-5'-phosphosulfate, isoenzyme AtSOT18 Co10, pH 9.0, 37°C
additional information
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0.05159 Vmax desulfobenzylglucosinolate, isoenzyme AtSOT18 Co10, pH 9.0, 37°C
additional information
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0.06599 Vmax 3'-phosphoadenosine-5'-phosphosulfate, isoenzyme AtSOT16 C24, pH 9.0, 37°C
additional information
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isoenzyme AtSOT16 C24 best substrate: 2-phenylethyl-glucosinolate
additional information
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isoenzyme AtSOT17 C24 best substrate: benzylglucosinolate
additional information
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isoenzyme AtSOT18 C24 best substrate: 6-methylthiohexylglucosinolate
additional information
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isoenzyme AtSOT18 Co10 best substrate: benzylglucosinolate
additional information
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isoenzyme AtSOT18G301D best substrate: 4-methylthiobutylglucosinolate
additional information
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isoenzyme AtST5a: best substrate: indole-3-methyl-desulfoglucosinolate, other substrates: benzyl-desulfoglucosinolate, 4-methylthiobutyl-desulfoglucosinolate, 4-methoxyindole-3-methyl-desulfoglucosinolate, N-methoxyindole-3-methyl-desulfoglucosinolate. pH 7.0, 30°C
additional information
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isoenzyme AtST5b: best substrate: 7-methylthioheptyl-desulfoglucosinolate, other substrates: 8-methylthiooctyl-desulfoglucosinolate, 4-methylthiobutyl-desulfoglucosinolate, benzyl-desulfoglucosinolate, indole-3-methyl-desulfoglucosinolate, 8-methylsulfinyloctyl-desulfoglucosinolate, 3-butenyl-desulfoglucosinolate. pH 7.0, 30°C
additional information
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isoenzyme AtST5c: best substrate: 8-methylthiooctyl-desulfoglucosinolate, other substrates: 7-methylthioheptyl-desulfoglucosinolate, benzyl-desulfoglucosinolate, 3-butenyl-desulfoglucosinolate, 4-methylthiobutyl-desulfoglucosinolate, 8-methylsulfinyloctyl-desulfoglucosinolate, 4-methylsulfinylbutyl-desulfoglucosinolate. pH 7.0, 30°C
additional information
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additional information
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additional information
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additional information
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additional information
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8.5 - 9
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maximal activity in Tris-HCl buffer
9
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9
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maximal activity in Tris-HCl buffer
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7 - 9.5
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about 65% of maximal activity at pH 7.0 and pH 9.5
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25 - 40
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about 85% of maximal activity at 25°C and about half-maximal activity at 40°C
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UniProt
brenda
rapeseed, cv. Westar
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brenda
cv. 526
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brenda
savoy cabbage
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brenda
at least 12 paralogues of desulfoglucosinolate sulfotransferase
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brenda
no.5089, curled cress
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brenda
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brenda
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brenda
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brenda
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UniProt
brenda
ecotype C24, ecotype Co10
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brenda
ecotype C24, ecotype Col-0
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brenda
three paralogues of desulfoglucosinolate sulfotransferase
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brenda
cv. Cutlass
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brenda
cv. Domo
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brenda
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brenda
cv. R-500
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brenda
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derived from hypocotyls
brenda
additional information
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expression of the gene paralogues is not tissue-specific but varies greatly depending on the tissue type. The expression is also developmentally regulated for some paralogues but not for others
brenda
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etiolated
brenda
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brenda
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tissue distribution
brenda
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tissue distribution
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brenda
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brenda
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brenda
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brenda
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-
brenda
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etiolated
brenda
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etiolated
brenda
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etiolated
brenda
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etiolated
brenda
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-
brenda
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brenda
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subcellular distribution
brenda
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subcellular distribution
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brenda
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brenda
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brenda
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metabolism
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the enzyme is involved in the glucosinolate biosynthesis pathway, glucosinolates play important roles in plant defense against herbivores and microbes, as well as in human nutrition
metabolism
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the enzyme is involved in the glucosinolate biosynthesis pathway, glucosinolates play important roles in plant defense against herbivores and microbes, as well as in human nutrition
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SOT16_ARATH
338
0
39219
Swiss-Prot
other Location (Reliability: 2 )
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39200
-
ecotype Co10, isoenzyme AtSOT16, calculated
39900
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ecotype Co10, isoenzyme AtSOT17, calculated
40500
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ecotype Co10, isoenzyme AtSOT18, calculated
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monomer
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1 * 31000-55000, SDS-PAGE
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G301D
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isoenzyme AtSOT18 C24, 25times higher specific activity with desulfobenzylglucosinolate
N339K
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to date no purification of the protein under native conditions
additional information
generation of two chimeric cytochrome P450 enzymes from CYP79A2 and CYP83B1 are constructed and attempted to be functionally expressed in Escherichia coli strain BL21(DE3). The Escherichia coli cystathionine beta-lyase is used to replace the plant-derived CS lyase whose active form cannot be expressed in Escherichia coli. Recomstruction of the BITC biosynthesis pathway from plants in the bacteria, involving CYP79A2 and CYP83B1, and the glutathione S-transferase, gamma-glutamyl peptidase, C-S lyase, glucosyltransferase, desulfoglucosinolate:PAPS sulfotransferase, and myrosinase are encoded by genes GSTF, GGP1, SUR1, UGT74B1, SOT16, and MYR, respectively, overview. Expression of codon-optimized sulfotransferase gene SOT16 from Arabidopsis thaliana fails because of the formation of inclusion bodies, SOT16 is successfully replaced for SOT18 (EC 2.8.2.38)
additional information
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generation of two chimeric cytochrome P450 enzymes from CYP79A2 and CYP83B1 are constructed and attempted to be functionally expressed in Escherichia coli strain BL21(DE3). The Escherichia coli cystathionine beta-lyase is used to replace the plant-derived CS lyase whose active form cannot be expressed in Escherichia coli. Recomstruction of the BITC biosynthesis pathway from plants in the bacteria, involving CYP79A2 and CYP83B1, and the glutathione S-transferase, gamma-glutamyl peptidase, C-S lyase, glucosyltransferase, desulfoglucosinolate:PAPS sulfotransferase, and myrosinase are encoded by genes GSTF, GGP1, SUR1, UGT74B1, SOT16, and MYR, respectively, overview. Expression of codon-optimized sulfotransferase gene SOT16 from Arabidopsis thaliana fails because of the formation of inclusion bodies, SOT16 is successfully replaced for SOT18 (EC 2.8.2.38)
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10.5
-
t1/2: 1 h, 4°C
643823
6
-
t1/2: 1 h, 4°C
643823
additional information
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activity loss due to instability at pH values near the isoelectric point 5.2
643824
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45
-
t1/2: 1 h, 20 mM Tris-HCl buffer, pH 7.5, 14 mM 2-mercaptoethanol
40
-
up to, stable
40
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at least 1 h, inactivation above
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bovine serum albumin, required for stabilizing
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MgCl2, 2-mercaptoethanol, DTT and GSH do not stabilize
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-20°C, 0.25 M sucrose and bovine serum albumin, 6 months
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-20°C, 20 mM Tris buffer, pH 7.5, 14 mM 2-mercaptoethanol, 10% glycerol, at least 2 months
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4°C, 14 mM 2-mercaptoethanol, t1/2: about 2 weeks
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4°C, more than 50% loss of activity within 48 h
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nickel-nitrilotriacetic acid-agarose
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persistently co-purified with EC 2.4.1.195
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co-expression of the enzyme with myrosinase from Brevicoryne brassicae in Escherichia coli, expression of codon-optimized sulfotransferase gene SOT16 from Arabidopsis thaliana fails because of the formation of inclusion bodies
DNA and amino acid sequence determination and analysis, gene structure, phylogenetic tree, genomic study of genes involved in glucosinolate biosynthesis, comparison with Arabidopsis thaliana genome, overview
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DNA and amino acid sequence determination and analysis, gene structure, phylogenetic tree, genomic study of genes involved in glucosinolate biosynthesis, comparison with Brassica rapa genome, overview
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expression in Escherichia coli M15
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Jain, J.C.; Reed, D.W.; Groot Wassink, J.W.D.; Underhill, E.W.
A radioassay of enzymes catalyzing the glucosylation and sulfation steps of glucosinolate biosynthesis in Brassica species
Anal. Biochem.
178
137-140
1989
Brassica rapa subsp. oleifera, Brassica juncea, Brassica napus, Brassica nigra, Brassica oleracea
brenda
Jain, J.C.; Michayluk, M.R.; Groot Wassink, J.W.D.; Underhill, E.W.
Distribution of enzymes catalyzing the glycosylation and sulfation steps of glucosinolate biosynthesis in Brassica juncea seedlings and cultured cells
Plant Sci.
64
25-29
1989
Brassica juncea
-
brenda
Jain, J.C.; Groot Wassink, J.W.D.; Reed, D.W.; Underhill, E.W.
Persistent co-purification of enzymes catalyzing the sequential glucosylation and sulfation steps in glucosinolate biosynthesis
J. Plant Physiol.
136
356-361
1990
Brassica juncea
-
brenda
Glendening, T.M.; Poulton, J.E.
Partial purification and characterization of a 3'-phosphoadenosine 5'-phosphosulfate: desulfoglucosinolate sulfotransferase from cress (Lepidium sativum)
Plant Physiol.
94
811-816
1990
Arabidopsis thaliana, Brassica rapa subsp. oleifera, Lepidium sativum, Sinapis alba, Tropaeolum majus
brenda
Jain, J.C.; Groot Wassink, J.W.D.; Kolenovsky, A.D.; Underhill, E.W.
Purification and properties of 3'-phosphoadenosine 5'-phosphosulfate: desulphoglucosinolate sulphotransefrase from Brassica juncea cell cultures
Phytochemistry
29
1425-1428
1990
Brassica juncea
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brenda
Klein, M.; Reichelt, M.; Gershenzon, J.; Papenbrock, J.
The three desulfoglucosinolate sulfotransferase proteins in Arabidopsis have different substrate specificities and are differentially expressed
FEBS J.
273
122-136
2006
Arabidopsis thaliana
brenda
Piotrowski, M.; Schemenewitz, A.; Lopukhina, A.; Muller, A.; Janowitz, T.; Weiler, E.W.; Oecking, C.
Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure
J. Biol. Chem.
279
50717-50725
2004
Arabidopsis thaliana
brenda
Zang, Y.X.; Kim, H.U.; Kim, J.A.; Lim, M.H.; Jin, M.; Lee, S.C.; Kwon, S.J.; Lee, S.I.; Hong, J.K.; Park, T.H.; Mun, J.H.; Seol, Y.J.; Hong, S.B.; Park, B.S.
Genome-wide identification of glucosinolate synthesis genes in Brassica rapa
FEBS J.
276
3559-3574
2009
Arabidopsis thaliana, Brassica rapa
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Liu, F.; Yang, H.; Wang, L.; Yu, B.
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5
1557-1565
2016
Arabidopsis thaliana (Q9C9D0), Arabidopsis thaliana Col-0 (Q9C9D0)
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