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Information on EC 2.4.1.195 - N-hydroxythioamide S-beta-glucosyltransferase
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2.4.1.195 N-hydroxythioamide S-beta-glucosyltransferaseIUBMB Comments
The enzyme specifically glucosylates the thiohydroximate functional group. It is involved in the biosynthesis of glucosinolates in cruciferous plants, and acts on aliphatic, aromatic, and indolic substrates.
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
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Synonyms
uridine diphosphoglucose (udpglucose):thiohydroximate glucosyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
desulfoglucosinolate-uridine diphosphate glucosyltransferase
-
-
-
-
thiohydroximate beta-D-glucosyltransferase
-
-
-
-
uridine diphosphoglucose-thiohydroximate glucosyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + (E)-2-(1H-indol-3-yl)-1-thioacetohydroximate = UDP + desulfoglucobrassicin
(3)
-
-
-
UDP-alpha-D-glucose + (Z)-2-phenyl-1-thioacetohydroximate = UDP + desulfoglucotropeolin
(1)
-
-
-
UDP-alpha-D-glucose + an (E)-omega-(methylsulfanyl)alkyl-thiohydroximate = UDP + an aliphatic desulfoglucosinolate
(2)
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-alpha-D-glucose:N-hydroxy-2-phenylethanethioamide S-beta-D-glucosyltransferase
The enzyme specifically glucosylates the thiohydroximate functional group. It is involved in the biosynthesis of glucosinolates in cruciferous plants, and acts on aliphatic, aromatic, and indolic substrates.
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CAS REGISTRY NUMBER
COMMENTARY
9068-14-8
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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
UDP-glucose + 2-(3-indolyl)acetothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-2-(3-indoyl)acetothiohydroximate
-
-
-
-
?
UDP-glucose + 3-phenylpropanothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-3-phenylpropanothiohydroximate
-
-
-
-
?
UDP-glucose + 4-methylthiobutyrothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-4-methylthiobutyrothiohydroximate
-
relative reaction rate 77%
-
-
?
UDP-glucose + benzothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-benzothiohydroximate
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relative reaction rate 10%
-
-
?
UDP-glucose + isobutyrothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-isobutyrothiohydroximate
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relative reaction rate 41%
-
-
?
UDPglucose + butyrothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-butyrothiohydroximate
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relative reaction rate 70%
-
-
?
UDPglucose + propiothiohydroximate
UDP + S-(alpha-D-glucopyranosyl)-propiothiohydroximate
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relative reaction rate 50%
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
catalyses the penultimate reaction in glucosinolate biosynthesis
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
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biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
second to last step in glucosinolate biosynthesis
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
integral step in the biosynthesis of benzylglucosinolate
-
-
?
additional information
?
-
-
the oxygen analog phenylacetohydroximate and the hydroxylated phenolic substances quercetin and caffeic acid are not glucosylated
-
-
?
additional information
?
-
-
acetothiohydroximate, phenylacetohydroximic acid, ethanol, 2-mercaptoethanol and cysteine hydrochloride are no substrates
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
catalyses the penultimate reaction in glucosinolate biosynthesis
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
second to last step in glucosinolate biosynthesis
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
biosynthetic pathway for glucosinolates
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
-
-
-
?
UDPglucose + phenylacetothiohydroximate
UDP + desulfoglucotropeolin
-
integral step in the biosynthesis of benzylglucosinolate
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
purified enzyme lacks an absolute requirement for metal ions
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
iodoacetic acid and 5,5'-dithio-bis-(2-nitrobenzoic acid) are less inhibitory
-
additional information
-
no inhibition by KCN or iodoacetic acid, only moderately inhibited by N-ethylmaleimide
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-mercaptoethanol
-
1.0 mM, relative activity 250%, 10 mM, relative activity 260%, in absence enzyme solutions will lose up to 35% activity in 1 week, activity is not recoverable by addition of 2-mercaptoethanol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7.5
-
greater activity in phosphate and Tris-HCl buffers than in Tris-maleate
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
cauliflower, ssp. botrytis cv Snowball, self-blanching type white and open type brown
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-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
located outside the plastids and mitochondria, not excluded association with endoplasmic reticulum and or vacuoles
brenda
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located outside the plastids and mitochondria, not excluded association with endoplasmic reticulum and or vacuoles
-
brenda
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). U74B1_ARATH
460
0
51002
Swiss-Prot
other Location (Reliability: 3)
A0A5B6YSN5_DAVIN
178
0
20018
TrEMBL
other Location (Reliability: 4)
A0A151QQB5_CAJCA
213
0
24637
TrEMBL
Mitochondrion (Reliability: 4)
A0A2P6R459_ROSCH
465
0
51253
TrEMBL
other Location (Reliability: 4)
A0A5B6Z7Q6_DAVIN
357
0
39478
TrEMBL
other Location (Reliability: 4)
A0A2P6S709_ROSCH
170
0
18810
TrEMBL
other Location (Reliability: 3)
A0A7C8ZTG2_OPUST
368
0
40642
TrEMBL
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
55500
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 40
-
stable up to 30°C for at least 1 h, activity is lost quickly at 40°C or greater
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-15°C, freeze-dried protein, specific activity remains unchanged for more than 3 months
-
0°C, storage at temperatures below with or without glycerol results in substantial loss of activity
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
nutrition
agriculture
-
glucosinolates have antinutritional properties and causes acute and chronic diseases, particularly monogastrics, in domestic animals, great nutritional and therefore economic concern, since the meal fraction is directed to animal feed markets as a protein source, presence of glucosinolates in the meal precludes its use as a feed for nonruminants, this results in a worldwide effort to breed low glucosinolate varieties of rapeseed, beside traditional plant breeding there are molecular genetic studies and modification of these pathways
agriculture
-
glucosinolates have antinutritional properties and causes acute and chronic diseases, particularly monogastrics, in domestic animals, great nutritional and therefore economic concern, since the meal fraction is directed to animal feed markets as a protein source, presence of glucosinolates in the meal precludes its use as a feed for nonruminants, this results in a worldwide effort to breed low glucosinolate varieties of rapeseed, beside traditional plant breeding there are molecular genetic studies and modification of these pathways
nutrition
-
glucosinolates have antinutritional properties and causes acute and chronic diseases, particularly monogastrics, in domestic animals, great nutritional and therefore economic concern, since the meal fraction is directed to animal feed markets as a protein source, presence of glucosinolates in the meal precludes its use as a feed for nonruminants, this results in a worldwide effort to breed low glucosinolate varieties of rapeseed, beside traditional plant breeding there are molecular genetic studies and modification of these pathways
nutrition
-
glucosinolates have antinutritional properties and causes acute and chronic diseases, particularly monogastrics, in domestic animals, great nutritional and therefore economic concern, since the meal fraction is directed to animal feed markets as a protein source, presence of glucosinolates in the meal precludes its use as a feed for nonruminants, this results in a worldwide effort to breed low glucosinolate varieties of rapeseed, beside traditional plant breeding there are molecular genetic studies and modification of these pathways
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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, Brassica juncea Coss
-
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
Matsuo, M.; Underhill, E.W.
Purification and properties of a UDP glucose:thiohydroximate glucosyltransferase from higher plants
Phytochemistry
10
2279-2288
1971
Armoracia rusticana, Nasturtium officinale, Sinapis alba, Tropaeolum majus, Nasturtium officinale R.Br.
-
brenda
Reed, D.W.; Davin, L.; Jain, J.C.; Deluca, V.; Nelson, L.; Underhill, E.W.
Purification and properties of UDP-glucose: thiohydroximate glucosyltransferase from Brassica napus L. seedlings
Arch. Biochem. Biophys.
305
526-532
1993
Brassica napus
brenda
Groot Wassink, J.W.D.; Reed, D.W.; Kolenovsky, A.D.
Immunopurification and immunocharacterization of the glucosinolate biosynthetic enzyme thiohydroximate S-glucosyltransferase
Plant Physiol.
105
425-433
1994
Brassica rapa subsp. oleifera, Brassica carinata, Brassica juncea, Brassica napus, Brassica nigra, Brassica oleracea
brenda
Guo, L.; Poulton, E.
Partial purification and characterization of Arabidopsis thaliana UDPG:thiohydroximate glucosyltransferase
Phytochemistry
36
1133-1138
1994
Arabidopsis thaliana
-
brenda
Marillia, E.F.; MacPherson, J.M.; Tsang, E.W.T.; Van Audenhove, K.; Keller, W.A.; Groot Wassink, J.W.D.
Molecular cloning of a Brassica napus thiohydroximate S-glucosyltransferase gene and its expression in Escherichia coli
Physiol. Plant.
113
176
2001
Brassica napus
brenda
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