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3'-phosphoadenylyl sulfate + 3-methylthiopropyl desulfoglucosinolate
adenosine 3',5'-bisphosphate + 3-methylthiopropyl glucosinolate
3'-phosphoadenylyl sulfate + desulfo-2-phenylethyl glucosinolate
adenosine 3',5'-bisphosphate + 2-phenylethyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-3-butenylglucosinolate
adenosine 3',5'-bisphosphate + 3-butenylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-3-methylthiopropyl glucosinolate
adenosine-3',5'-bisphosphate + 3-methylthiopropyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-3-methylthiopropylglucosinolate
adenosine 3',5'-bisphosphate + 3-methylthiopropylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-4-methylthiobutyl glucosinolate
adenosine-3',5'-bisphosphate + 4-methylthiobutyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-4-methylthiobutylglucosinolate
adenosine 3',5'-bisphosphate + 4-methylthiobutylglucosinolate
3'-phosphoadenylyl sulfate + desulfo-5-methylthiopentylglucosinolate
adenosine 3',5'-bisphosphate + 5-methylthiopentylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-6-methylthiohexylglucosinolate
adenosine 3',5'-bisphosphate + 6-methylthiohexylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-7-methylthioheptyl glucosinolate
adenosine-3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
3'-phosphoadenylyl sulfate + desulfo-7-methylthioheptylglucosinolate
adenosine 3',5'-bisphosphate + 7-methylthioheptylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-8-methylthiooctyl glucosinolate
adenosine-3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
3'-phosphoadenylyl sulfate + desulfo-8-methylthiooctylglucosinolate
adenosine 3',5'-bisphosphate + 8-methylthiooctylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-benzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-indol-3-yl-methyl glucosinolate
adenosine-3',5'-bisphosphate + indol-3-yl-methyl glucosinolate
3'-phosphoadenylyl sulfate + desulfo-indole-3-methylglucosinolate
adenosine 3',5'-bisphosphate + indole-3-methylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfobenzylglucosinolate
adenosine 3',5'-bisphosphate + benzylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfosinigrin
adenosine 3',5'-bisphosphate + sinigrin
adenosine 3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
3'-phosphoadenylyl sulfate + 7-methylthioheptyl desulfoglucosinolate
adenosine 3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
3'-phosphoadenylyl sulfate + 8-methylthiooctyl desulfoglucosinolate
adenosine 3',5'-bisphosphate + glucoerucin
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
adenosine 3',5'-bisphosphate + sinigrin
3'-phosphoadenylyl sulfate + desulfosinigrin
sinigrin binding is facilitated by hydrogen bonding with residues Arg51, Glu54, Thr96, Tyr130, His155 and Tyr306. The guanidinium group of Arg51 interacts with the 6'-hydroxyl group of the glucopyranose of the glucosinolate. The carboxyl group of Glu54 interacts with the 4'- and the 6'-hydroxyl groups. The hydroxyl of Tyr306 forms a hydrogen bond with the oxygen in the glucopyranose ring. The sulfate moiety is stabilized by hydrogen bonds with Thr96, Tyr130 and His155. In this positioning the sulfate and phosphate groups of sinigrin and PAP, respectively, are located within the hydrogen bond distance from each other. Analysis of the mechanism of PAPS binding
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-
?
additional information
?
-
3'-phosphoadenylyl sulfate + 3-methylthiopropyl desulfoglucosinolate
adenosine 3',5'-bisphosphate + 3-methylthiopropyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + 3-methylthiopropyl desulfoglucosinolate
adenosine 3',5'-bisphosphate + 3-methylthiopropyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-4-methylthiobutylglucosinolate
adenosine 3',5'-bisphosphate + 4-methylthiobutylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-4-methylthiobutylglucosinolate
adenosine 3',5'-bisphosphate + 4-methylthiobutylglucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-7-methylthioheptyl glucosinolate
adenosine-3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-7-methylthioheptyl glucosinolate
adenosine-3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
preferred substrate of isozyme SOT18 of ecotype C24
-
-
?
3'-phosphoadenylyl sulfate + desulfo-8-methylthiooctyl glucosinolate
adenosine-3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-8-methylthiooctyl glucosinolate
adenosine-3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
preferred substrate of isozyme SOT18 of ecotype C24
-
-
?
3'-phosphoadenylyl sulfate + desulfo-indol-3-yl-methyl glucosinolate
adenosine-3',5'-bisphosphate + indol-3-yl-methyl glucosinolate
-
-
-
?
3'-phosphoadenylyl sulfate + desulfo-indol-3-yl-methyl glucosinolate
adenosine-3',5'-bisphosphate + indol-3-yl-methyl glucosinolate
preferred substrate of isozyme SOT16 of ecotype C24
-
-
?
3'-phosphoadenylyl sulfate + desulfosinigrin
adenosine 3',5'-bisphosphate + sinigrin
-
-
-
?
3'-phosphoadenylyl sulfate + desulfosinigrin
adenosine 3',5'-bisphosphate + sinigrin
-
-
-
?
adenosine 3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
3'-phosphoadenylyl sulfate + 7-methylthioheptyl desulfoglucosinolate
-
-
-
?
adenosine 3',5'-bisphosphate + 7-methylthioheptyl glucosinolate
3'-phosphoadenylyl sulfate + 7-methylthioheptyl desulfoglucosinolate
-
-
-
?
adenosine 3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
3'-phosphoadenylyl sulfate + 8-methylthiooctyl desulfoglucosinolate
-
-
-
?
adenosine 3',5'-bisphosphate + 8-methylthiooctyl glucosinolate
3'-phosphoadenylyl sulfate + 8-methylthiooctyl desulfoglucosinolate
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoerucin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
adenosine 3',5'-bisphosphate + glucoiberverin
?
-
-
-
-
?
additional information
?
-
qualitative glucosinolate analysis in leaves of ecotype C24, overview
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-
?
additional information
?
-
qualitative glucosinolate analysis in leaves of ecotype C24, overview
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-
?
additional information
?
-
qualitative glucosinolate analysis in leaves of ecotype C24, overview
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-
?
additional information
?
-
-
qualitative glucosinolate analysis in leaves of ecotype C24, overview
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-
?
additional information
?
-
ecotype C24 isozyme SOT18 prefers the long-chain desulfoglucosinolates, 7-methylthioheptyl and 8-methylthiooctyl, derived from methionine. The substrate specificty of the isozyme SOT18 from ecotype Columbia-0 differs from the SOT18 from ecotype C24, detailed overview. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
ecotype C24 isozyme SOT18 prefers the long-chain desulfoglucosinolates, 7-methylthioheptyl and 8-methylthiooctyl, derived from methionine. The substrate specificty of the isozyme SOT18 from ecotype Columbia-0 differs from the SOT18 from ecotype C24, detailed overview. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
ecotype C24 isozyme SOT18 prefers the long-chain desulfoglucosinolates, 7-methylthioheptyl and 8-methylthiooctyl, derived from methionine. The substrate specificty of the isozyme SOT18 from ecotype Columbia-0 differs from the SOT18 from ecotype C24, detailed overview. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
-
ecotype C24 isozyme SOT18 prefers the long-chain desulfoglucosinolates, 7-methylthioheptyl and 8-methylthiooctyl, derived from methionine. The substrate specificty of the isozyme SOT18 from ecotype Columbia-0 differs from the SOT18 from ecotype C24, detailed overview. Substrate synthesis and optimization of the enzyme assay method, overview
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-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: isozyme SOT17 shows an increased specific activity with increasing chain length of desulfoglucosinolates derived from methionine. Substrate synthesis and optimization of the enzyme assay method, overview
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-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: isozyme SOT17 shows an increased specific activity with increasing chain length of desulfoglucosinolates derived from methionine. Substrate synthesis and optimization of the enzyme assay method, overview
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-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: isozyme SOT17 shows an increased specific activity with increasing chain length of desulfoglucosinolates derived from methionine. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
-
ecotype C24 isozyme substrate specificities: isozyme SOT17 shows an increased specific activity with increasing chain length of desulfoglucosinolates derived from methionine. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: preference of isozyme SOT16 for the indolic desulfoglucosinolate indol-3-yl-methylglucosinolate. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: preference of isozyme SOT16 for the indolic desulfoglucosinolate indol-3-yl-methylglucosinolate. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
ecotype C24 isozyme substrate specificities: preference of isozyme SOT16 for the indolic desulfoglucosinolate indol-3-yl-methylglucosinolate. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
-
ecotype C24 isozyme substrate specificities: preference of isozyme SOT16 for the indolic desulfoglucosinolate indol-3-yl-methylglucosinolate. Substrate synthesis and optimization of the enzyme assay method, overview
-
-
?
additional information
?
-
enzyme AtSOT18 prefers the long-chain ds-Gls 7-methylthioheptyl Gl and 8-methylthiooctyl Gl (8MTO), that are also derived from methionine
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-
additional information
?
-
-
enzyme AtSOT18 prefers the long-chain ds-Gls 7-methylthioheptyl Gl and 8-methylthiooctyl Gl (8MTO), that are also derived from methionine
-
-
-
additional information
?
-
usage of 3'-phosphoadenylyl-sulfate:aliphatic desulfoglucosinolate 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
?
-
usage of 3'-phosphoadenylyl-sulfate:aliphatic desulfoglucosinolate 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
?
-
enzyme AtSOT18 prefers the long-chain ds-Gls 7-methylthioheptyl Gl and 8-methylthiooctyl Gl (8MTO), that are also derived from methionine
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additional information
?
-
enzyme prefers long-chained methionine-derived desulfoglucosinolates desulfo4-methythiobutylglucosinolate and desulfo-5-methylthiopentylglucosinoate
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?
additional information
?
-
-
enzyme prefers long-chained methionine-derived desulfoglucosinolates desulfo4-methythiobutylglucosinolate and desulfo-5-methylthiopentylglucosinoate
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?
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0.06 - 0.25
3'-phosphoadenylyl sulfate
0.055 - 0.271
desulfo-3-methylthiopropylglucosinolate
0.043 - 0.13
desulfo-4-methylthiobutylglucosinolate
0.05 - 0.1
desulfobenzylglucosinolate
0.055 - 0.1
glucoiberverin
additional information
additional information
-
0.06
3'-phosphoadenylyl sulfate
pH 9.0, 30°C
0.25
3'-phosphoadenylyl sulfate
pH 9.0, 30°C
0.055
desulfo-3-methylthiopropylglucosinolate
pH 9.0, 37°C, isozyme SOT18, ecotype Columbia-0
0.07
desulfo-3-methylthiopropylglucosinolate
pH 9.0, 37°C, isozyme SOT16
0.088
desulfo-3-methylthiopropylglucosinolate
pH 9.0, 37°C, isozyme SOT17
0.1
desulfo-3-methylthiopropylglucosinolate
pH 9.0, 37°C, isozyme SOT18, ecotype C24
0.271
desulfo-3-methylthiopropylglucosinolate
pH 9.0, 37°C
0.043
desulfo-4-methylthiobutylglucosinolate
pH 9.0, 37°C, isozyme SOT18, ecotype Columbia-0
0.065
desulfo-4-methylthiobutylglucosinolate
pH 9.0, 37°C, isozyme SOT17
0.08
desulfo-4-methylthiobutylglucosinolate
pH 9.0, 37°C, isozyme SOT16
0.09
desulfo-4-methylthiobutylglucosinolate
pH 9.0, 37°C
0.13
desulfo-4-methylthiobutylglucosinolate
pH 9.0, 37°C, isozyme SOT18, ecotype C24
0.05
desulfobenzylglucosinolate
pH 9.0, 30°C
0.1
desulfobenzylglucosinolate
pH 9.0, 30°C
0.043
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.058
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.06
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.081
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.096
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.13
glucoerucin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.055
glucoiberverin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.06
glucoiberverin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.067
glucoiberverin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.09
glucoiberverin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
0.1
glucoiberverin
-
in 80 mM Tris/HCl, pH 9.0, 9.2 mM MgCl2, at 37°C
additional information
additional information
kinetics
-
additional information
additional information
-
kinetics
-
additional information
additional information
kinetics, overview
-
additional information
additional information
kinetics, overview
-
additional information
additional information
kinetics, overview
-
additional information
additional information
-
kinetics, overview
-
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G301D
exchange of amino acid from ecotype C24 to that of ecotype Col0. 25fold increase in specific activity with desulfobenzylglucosinolate
H155A
site-directed mutagenesis, inactive mutant
K93A
site-directed mutagenesis, inactive mutant
N339K
exchange of amino acid from ecotype C24 to that of ecotype Col0, residue glycine at position 301 may play a critical role in substrate recognition
P136A
site-directed mutagenesis, the mutant shows unaltered activity compared to wild-type enzyme
T96A
site-directed mutagenesis, mutant Thr96Ala shows residual activity with the preferred substrates 3-methylthiopropyl desulfoglucosinolate and 8-methylthiooctyl desulfoglucosinolate (12fold reduction and 3fold reduction, respectively), while with sinigrin no activity is detected
T97A
site-directed mutagenesis, inactive mutant
Y130A
site-directed mutagenesis, inactive mutant
H155A
-
site-directed mutagenesis, inactive mutant
-
K93A
-
site-directed mutagenesis, inactive mutant
-
T96A
-
site-directed mutagenesis, mutant Thr96Ala shows residual activity with the preferred substrates 3-methylthiopropyl desulfoglucosinolate and 8-methylthiooctyl desulfoglucosinolate (12fold reduction and 3fold reduction, respectively), while with sinigrin no activity is detected
-
T97A
-
site-directed mutagenesis, inactive mutant
-
Y130A
-
site-directed mutagenesis, inactive mutant
-
additional information
generation of two chimeric cytochrome P450 enzymes from CYP79A2 and CYP83B1 are constructed and functionally expressed in Escherichia coli. The Escherichia coli cystathionine beta-lyase is used to replace the plant-derived CS lyase whose active form cannot be expressed in Escherichia coli strain BL21(DE3). Reconstruction 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, 3'-phosphoadenylyl-sulfate:aliphatic desulfoglucosinolate sulfotransferase, and myrosinase are encoded by genes GSTF, GGP1, SUR1, UGT74B1, SOT18, and MYR, respectively, overview
additional information
-
generation of two chimeric cytochrome P450 enzymes from CYP79A2 and CYP83B1 are constructed and functionally expressed in Escherichia coli. The Escherichia coli cystathionine beta-lyase is used to replace the plant-derived CS lyase whose active form cannot be expressed in Escherichia coli strain BL21(DE3). Reconstruction 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, 3'-phosphoadenylyl-sulfate:aliphatic desulfoglucosinolate sulfotransferase, and myrosinase are encoded by genes GSTF, GGP1, SUR1, UGT74B1, SOT18, and MYR, respectively, overview
-
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Klein, M.; Papenbrock, J.
Kinetics and substrate specificities of desulfo-glucosinolate sulfotransferases in Arabidopsis thaliana
Physiol. Plant.
135
140-149
2009
Arabidopsis thaliana (Q9C9C9), Arabidopsis thaliana (Q9C9D0), Arabidopsis thaliana (Q9FZ80), Arabidopsis thaliana
brenda
Luczak, S.; Forlani, F.; Papenbrock, J.
Desulfo-glucosinolate sulfotransferases isolated from several Arabidopsis thaliana ecotypes differ in their sequence and enzyme kinetics
Plant Physiol. Biochem.
63
15-23
2013
Arabidopsis thaliana, Arabidopsis thaliana ecotype C24, Arabidopsis thaliana ecotype Cvi-0, Arabidopsis thaliana ecotype Col-0, Arabidopsis thaliana ecotype Ws, Arabidopsis thaliana ecotype Bla-10, Arabidopsis thaliana ecotype Ler-1
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 (Q9C9C9), Arabidopsis thaliana (Q9FZ80)
-
brenda
Piotrowski, M.; Schemenewitz, A.; Lopukhina, A.; Mller, A.; Janowitz, T.; Weiler, E.; 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 (Q9C9C9), Arabidopsis thaliana (Q9FZ80)
brenda
Hirschmann, F.; Papenbrock, J.
The fusion of genomes leads to more options A comparative investigation on the desulfo-glucosinolate sulfotransferases of Brassica napus and homologous proteins of Arabidopsis thaliana
Plant Physiol. Biochem.
91
10-19
2015
Brassica napus (A0A0K1H0V2), Brassica napus
brenda
Liu, F.; Yang, H.; Wang, L.; Yu, B.
Biosynthesis of the high-value plant secondary product benzyl isothiocyanate via functional expression of multiple heterologous enzymes in Escherichia coli
ACS Synth. Biol.
5
1557-1565
2016
Arabidopsis thaliana (Q9C9C9), Arabidopsis thaliana Col-0 (Q9C9C9)
brenda
Hirschmann, F.; Krause, F.; Baruch, P.; Chizhov, I.; Mueller, J.W.; Manstein, D.J.; Papenbrock, J.; Fedorov, R.
Structural and biochemical studies of sulphotransferase 18 from Arabidopsis thaliana explain its substrate specificity and reaction mechanism
Sci. Rep.
7
4160
2017
Arabidopsis thaliana (Q9C9C9), Arabidopsis thaliana, Arabidopsis thaliana Col-0 (Q9C9C9)
brenda