Information on EC 2.4.1.128 - scopoletin glucosyltransferase

Substrates: transgenic plants over-expressing the salicylate- and pathogen-inducible glucosyltransferase. Activity of TOGT and the subsequent accumulation of glucosylated coumarins represent an important step in the cascade of events resulting in confinement of viral pathogens
Products: -

UDP-glucose + scopoletin

UDP + scopolin

660198, 660144

Substrates: -
Products: -

additional information

Substrates: the enzyme shows activity towards a number of coumarins including umbelliferone, scopoletin, isoscopoletin and esculetin, and flavonoids including a flavone, a flavanone and chalcones. No activity is detected with compounds characterized by a single aromatic ring, i.e. simple and acidic phenols
Products: -

additional information

Substrates: UGT73A25 appears to promote the formation of flavonoid rutinosides and a kaempferol diglucoside, while UGT73A24 does not
Products: -

additional information

Substrates: broad substrate specificity of NbUGT73A25, detailed overview. Enzymes UGT73A24 and UGT73A25 show the highest activity towards kaempferol
Products: -

show all columns Go to Natural Substrate Search

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

UDP-glucose + kaempferol

UDP + ?

Substrates: best substrate
Products: -

UDP-glucose + kaempferol

UDP + kaempferol 3,7-diglucoside

Substrates: -
Products: -

UDP-glucose + N-trans-feruloyl tyramine

UDP + ?

Substrates: -
Products: -

UDP-glucose + scopoletin

UDP + scopolin

4 entries

additional information

Substrates: UGT73A25 appears to promote the formation of flavonoid rutinosides and a kaempferol diglucoside, while UGT73A24 does not
Products: -

UDP-glucose + scopoletin

UDP + scopolin

Substrates: -
Products: -

UDP-glucose + scopoletin

UDP + scopolin

Substrates: -
Products: -

UDP-glucose + scopoletin

UDP + scopolin

660198

Substrates: pathogen-inducible enzyme. Over-expression leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance
Products: -

UDP-glucose + scopoletin

UDP + scopolin

show all columns Go to Metals and Ions Search

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METALS and IONS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

Na+

the addition of Na+ to buffered standard assays at concentration 1 and 10 mM has a stimulating effect on the glucosylation of scopoletin to 110% and 128%, respectively

additional information

not affected by Mg2+ and Ca2+

show all columns Go to Inhibitor Search

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

Cu2+

51.5% residual activity at 1 mM, 12% residual activity at 10 mM

Mn2+

40.9% residual activity at 1 mM, complete inhibition at 10 mM

Zn2+

27.1% residual activity at 1 mM, complete inhibition at 10 mM

show all columns Go to Activating Compound Search

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ACTIVATING COMPOUND

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

2,4-Dichlorophenoxyacetic acid

0.005 mM, 10fold activation

Go to Disease Search

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DISEASE

TITLE OF PUBLICATION

LINK TO PUBMED

Infections

Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y.

15509841

show all columns Go to KM Value Search

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.8818 - 1.2721

carvacrol

0.0022 - 0.0187

kaempferol

0.1103 - 0.2826

N-4-trans-coumaroyl tyramine

0.1505 - 0.1592

N-caffeoyl-O-methyl tyramine

1.4732 - 3.0307

N-trans-feruloyl tyramine

0.0035 - 0.0043

quercetin

0.0152 - 0.9123

scopoletin

8 entries

0.2772 - 1.065

UDP-glucose

5 entries

additional information

Michaelis-Menten kinetics

0.8818

carvacrol

recombinant enzyme, pH 7.5, 30°C

1.2721

carvacrol

recombinant enzyme, pH 7.5, 30°C

0.0022

kaempferol

recombinant enzyme, pH 7.5, 30°C

0.0187

kaempferol

recombinant enzyme, pH 7.5, 30°C

0.1103

N-4-trans-coumaroyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.2826

N-4-trans-coumaroyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.1505

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.1592

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

1.4732

N-trans-feruloyl tyramine

recombinant enzyme, pH 7.5, 30°C

3.0307

N-trans-feruloyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.0035

quercetin

recombinant enzyme, pH 7.5, 30°C

0.0043

quercetin

recombinant enzyme, pH 7.5, 30°C

0.0152

scopoletin

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.03897

scopoletin

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.04955

scopoletin

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.05183

scopoletin

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.06045

scopoletin

71C1 double mutant, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.112

scopoletin

at 37°C, pH not specified in the publication

0.3245

scopoletin

recombinant enzyme, pH 7.5, 30°C

0.9123

scopoletin

recombinant enzyme, pH 7.5, 30°C

0.2772

UDP-glucose

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.2826

UDP-glucose

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.8363

UDP-glucose

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

UDP-glucose

at 37°C, pH not specified in the publication

1.065

UDP-glucose

71C1 double mutant, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

show all columns Go to Turnover Number Search

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.811 - 0.967

carvacrol

0.341 - 0.589

kaempferol

0.01

N-4-trans-coumaroyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.06 - 0.07

N-caffeoyl-O-methyl tyramine

0.06

N-trans-feruloyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.264 - 0.65

quercetin

0.06 - 10.92

scopoletin

6 entries

0.811

carvacrol

recombinant enzyme, pH 7.5, 30°C

0.967

carvacrol

recombinant enzyme, pH 7.5, 30°C

0.341

kaempferol

recombinant enzyme, pH 7.5, 30°C

0.589

kaempferol

recombinant enzyme, pH 7.5, 30°C

0.06

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.07

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.264

quercetin

recombinant enzyme, pH 7.5, 30°C

0.65

quercetin

recombinant enzyme, pH 7.5, 30°C

0.06

scopoletin

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.766

scopoletin

recombinant enzyme, pH 7.5, 30°C

0.916

scopoletin

recombinant enzyme, pH 7.5, 30°C

1.11

scopoletin

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

10.07

scopoletin

71C1 double mutant, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

10.92

scopoletin

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

show all columns Go to kcat/KM Value Search

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kcat/KM VALUE [1/mMs^-1]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.76 - 0.92

carvacrol

31.5 - 155

kaempferol

0.035 - 0.09

N-4-trans-coumaroyl tyramine

0.4 - 0.44

N-caffeoyl-O-methyl tyramine

0.02 - 0.041

N-trans-feruloyl tyramine

61.4 - 185.71

quercetin

0.84 - 210.7

scopoletin

7 entries

0.21 - 13.05

UDP-glucose

5 entries

0.76

carvacrol

recombinant enzyme, pH 7.5, 30°C

0.92

carvacrol

recombinant enzyme, pH 7.5, 30°C

31.5

kaempferol

recombinant enzyme, pH 7.5, 30°C

155

kaempferol

recombinant enzyme, pH 7.5, 30°C

0.035

N-4-trans-coumaroyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.09

N-4-trans-coumaroyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.4

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.44

N-caffeoyl-O-methyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.02

N-trans-feruloyl tyramine

recombinant enzyme, pH 7.5, 30°C

0.041

N-trans-feruloyl tyramine

recombinant enzyme, pH 7.5, 30°C

61.4

quercetin

recombinant enzyme, pH 7.5, 30°C

185.71

quercetin

recombinant enzyme, pH 7.5, 30°C

0.84

scopoletin

recombinant enzyme, pH 7.5, 30°C

1.21

scopoletin

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

2.82

scopoletin

recombinant enzyme, pH 7.5, 30°C

28.48

scopoletin

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476)

28.48

scopoletin

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

166.6

scopoletin

71C1 double mutant

210.7

scopoletin

wild type

0.21

UDP-glucose

wild type, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

3.92

UDP-glucose

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476)

3.92

UDP-glucose

71C1/71C3 chimera including N-terminus of 71C1 (position 1-261) and C-terminus of 71C3 (position 256-476), 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

9.45

UDP-glucose

71C1 double mutant

show all columns Go to Specific Activity Search

13.05

UDP-glucose

wild type

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.00084

Duboisia myoporoides

activity in crude extracts

0.0116

0.03

71C3, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

0.114

cells cultured in the presence of 0.005 mM 2,4-dichlorophenoxyacetic acid

1.356

71C1, 50 mM Tris-HCl, pH 7.0, 14 mM 2-mercaptoethanol, 30°C

show all columns Go to pH Optimum Search

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.5

3 entries

7.5

in Tris buffer

7.5

show all columns Go to Temperature Optimum Search

assay at

7.5

assay at

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

show all columns Go to Organism Search

assay at

assay at

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks include all textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks + FRENDAco-occurrence of enzyme names and organism names (less precise)

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

UniProt

brenda

brenda

brenda

show all columns Go to Source Tissue Search

brenda

brenda

Bright Yellow

brenda

cv. Samsun NN

brenda

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

callus

3 entries

cell suspension culture

brenda

brenda

brenda

cell culture

brenda

brenda

brenda

show all columns Go to Localization Search

brenda

brenda

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

cytosol

absent from isolated vacuoles, most probably located in the cytosol

5829

488530

brenda

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Highest Expressing Human Cell Lines

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Cell Line Links

Gene Links

show all columns Go to General Information Search

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

evolution

Nicotiana benthamiana enzymes UGT73A24 and UGT73A25 show 95% sequence identity

metabolism

while in Nicotiana tabacum, TOGT (tobacco UGT) glucosylates scopoletin after treatment with salicylate, fungal elicitors and the tobacco mosaic virus, enzymes NbUGT73A24 and NbUGT73A25 produce glucosides of phytoalexin N-feruloyl tyramine, which may strengthen cell walls to prevent the intrusion of pathogens, and flavonols after agroinfiltration of the corresponding genes in Nicotiana benthamiana

physiological function

4 entries

physiological function

glycosyltransferases of family 1 are capable of transferring sugar moieties from activated sugar donors to a wide range of small lipophilic acceptors leading to an increase in water solubility, improved chemical stability and altered biological activity of the sugar conjugates, in plants, family 1 glycosyltransferases play an important role in metabolic homeostasis, regulation of phytohormone activities and detoxification of xenobiotics such as herbicides and pesticides

physiological function

glycosyltransferases of family 1 are capable of transferring sugar moieties from activated sugar donors to a wide range of small lipophilic acceptors leading to an increase in water solubility, improved chemical stability and altered biological activity of the sugar conjugates, in plants, family l glycosyltransferases play an important role in metabolic homeostasis, regulation of phytohormone activities and detoxification of xenobiotics such as herbicides and pesticides

physiological function

NbUGT73A24 produces glucosides of phytoalexin N-feruloyl tyramine, which may strengthen cell walls to prevent the intrusion of pathogens, and flavonols after agroinfiltration of the corresponding genes in Nicotiana benthamiana

physiological function

NbUGT73A25 produces glucosides of phytoalexin N-feruloyl tyramine, which may strengthen cell walls to prevent the intrusion of pathogens, and flavonols after agroinfiltration of the corresponding genes in Nicotiana benthamiana

Go to AA Sequence and Transmembrane Helices SearchGo to Localization Prediction

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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).

Q9AT54 pBLAST

SCGT_TOBAC

476

53648

Swiss-Prot

Show Sequence

O82381 pBLAST

U71C1_ARATH

481

53875

Swiss-Prot

Show Sequence

Q9LML7 pBLAST

U71C3_ARATH

476

52901

Swiss-Prot

Show Sequence

other Location (Reliability: 2)

show all columns Go to Molecular Weight Search

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

45000

native PAGE

51000

x * 51000, SDS-PAGE

80000

by SDS-PAGE, approximate molecular weight of wild-type enzyme and mutants

show all columns Go to Subunit Search

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

x * 51000, SDS-PAGE

show all columns Go to Protein Variants Search

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PROTEIN VARIANTS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

D257E/S260L

by site-directed mutagenesis

D262E/N265Q

by site-directed mutagenesis

additional information

overexpression of UGT73A24 and UGT73A25 leads to a significant reduction in the level of the pathogen-responsive metabolites, including phenylalanine and tryptophan although the latter are not substrates of the encoded enzymes

Go to Purification (commentary) Search

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PURIFICATION (Commentary)

ORGANISM

UNIPROT

LITERATURE

ammonium sulfate precipitation, phenyl-Sepharose column chromatographyand DEAE Sepharose column chromatography

ammonium sulfate, Sephadex G-100, DEAE-cellulose, hydroxyapatite

Go to Cloned (commentary) Search

recombinant proteins are purified by affinity chromatography using GST-Sepharose 4B

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

DNA and amino acid sequence determination and analysis, recombinant overexpression of UGT73A24 in Nicotiana benthamiana leaves by agroinfiltration to identify the natural substrates

DNA and amino acid sequence determination and analysis, recombinant overexpression of UGT73A25 in Nicotiana benthamiana leaves by agroinfiltration to identify the natural substrates

expression in Escherichia coli, transgenic plants over-expressing the enzyme in leaves and in roots

generation of plants overexpressing the enzyme. Over-expression leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance

660198

recombinant and mutant glycosyltransferase 71C1 is expressed as fusion protein tagged with a 26 kDa GST protein at the N-terminus in Escherichia coli BL21, production of a chimeric mutant derived from 2 Arabidopsis glucosyltransferases, 71C1 and 71C3, the chimera contains the N-terminal domain of 71C1 and the C-terminal domain of 71C3

recombinant and mutant glycosyltransferase 71C3 is expressed as fusion protein tagged with a 26 kDa GST protein at the N-terminus in Escherichia coli BL21, production of a chimeric mutant derived from 2 Arabidopsis glucosyltransferases, 71C1 and 71C3, the chimera contains the N-terminal domain of 71C1 and the C-terminal domain of 71C3

top print hide References Search

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

Hino, F.; Okazaki, M.; Miura, Y.

Effect of 2,4-dichlorophenoxyacetic acid on glucosylation of scopoletin to scopolin in tobacco tissue culture

Plant Physiol.

810-813

1982

Nicotiana tabacum

16662301

brenda

488529

Betry, P.; Fliniaux, M.A.; Mackova, M.; Gillet, F.; Macek, T.; Jacquin-Dubreuil, A.

Scopoletin-glucosyltransferase activity from Duboisia myoporoides; improvement of cultivation conditions and crude extract preparation procedure

J. Plant Physiol.

146

503-507

1995

Duboisia myoporoides

brenda

488530

Taguchi, G.; Fujikawa, S.; Yazawa, T.; Kodaira, R.; Hayashida, N.; Shimosaka, M.; Okazaki, M.

Scopoletin uptake from culture medium and accumulation in the vacuoles after conversion to scopolin in 2,4-D-treated tobacco cells

Plant Sci.

151

153-161

2000

Nicotiana tabacum

10808071

brenda

Matros, A.; Mock, H.P.

Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y

Plant Cell Physiol.

1185-1193

2004

Nicotiana tabacum

15509841

brenda

660198

Gachon, C.; Baltz, R.; Saindrenan, P.

Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance

Plant Mol. Biol.

137-146

2004

Nicotiana tabacum

15159640

brenda

Weis, M.; Lim, E.K.; Bruce, N.C.; Bowles, D.J.

Engineering and kinetic characterisation of two glucosyltransferases from Arabidopsis thaliana

Biochimie

830-834

2008

Arabidopsis thaliana (O82381), Arabidopsis thaliana (Q9LML7)

18295607

brenda

Piovan, A.; Cozza, G.; Caniato, R.; Moro, S.; Filippini, R.

A novel glucosyltransferase from Catharanthus roseus cell suspensions

Process Biochem.

655-659

2010

Catharanthus roseus

brenda