Information on EC 2.4.1.202 - 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucosyltransferase

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The expected taxonomic range for this enzyme is: Zea mays

EC NUMBER
COMMENTARY hide
2.4.1.202
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RECOMMENDED NAME
GeneOntology No.
2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one = UDP + (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
show the reaction diagram
(2)
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UDP-alpha-D-glucose + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one = UDP + (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
show the reaction diagram
(1)
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Benzoxazinoid biosynthesis
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DIBOA-glucoside biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucosyltransferase
The enzyme is involved in the detoxification of the benzoxazinoids DIBOA (2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one) and DIMBOA (2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one) which are stored as the respective non-toxic glucosides in the vacuoles in some plants, most commonly from the family of Poaceae (grasses). Benzoxazinoids are known to exhibit antimicrobial, antifeedant, and antiinsecticidal effects and are involved in the interaction of plants with other plants, insects, or microorganisms.
CAS REGISTRY NUMBER
COMMENTARY hide
122544-56-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
two different enzymes with different substrate specificities, genes Bx8 and Bx9
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-glucose + 2,4-dihydroxy-1,4-benzoxazin-3-one
UDP + 2,4-dihydroxy-2H-1,4-benzoxazin-3-one 2-D-glucoside
show the reaction diagram
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peak 1 glucosyltransferase has 3.6% of activity compared to activity towards 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, peak 2 glucosyltransferase has 57% of activity compared to activity towards 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
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?
UDP-glucose + 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one
UDP + 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside
show the reaction diagram
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-
?
UDP-glucose + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
UDP + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside
show the reaction diagram
UDP-glucose + 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one
UDP + 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside
show the reaction diagram
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low glucosylation efficiency
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?
UDP-glucose + 2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
UDP + 2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside
show the reaction diagram
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?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-glucose + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
UDP + 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-D-glucoside
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
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at 5 mM, stimulation of 42%
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CaCl2
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5 mM, stimulation
MgCl2
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5 mM, stimulation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Cu2+
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5 mM, 3% remaining activity
EDTA
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16% decrease of activity
Fe2+
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5 mM, 5% remaining activity
N-ethylmaleimide
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at 1 mM, 96% decrease of activity, after addition of dithioerythritol, full activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
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5 mM, stimulation of 79%
ascorbate
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at 5 mM, stimulation of 42%
dithioerythritol
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5 mM, stimulation of 96%
glutathione
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5 mM, stimulation of 92%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.638
2,4-dihydroxy-1,4-benzoxazin-3-one
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enzyme in peak 2
0.061 - 1.3
2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one
0.071 - 0.217
2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
0.081 - 0.096
UDP-glucose
0.28 - 0.286
UDPglucose
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.5
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2-hydroxy-2H-1,4-benzoxazin-3(4H)-one, BX8-gene encoded protein; 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one, BX9-gene encoded protein
1.218
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enzyme in peak 1 and peak 2
1.4
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2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, BX8-gene encoded protein
2.6
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2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one as substrate, BX9-gene encoded protein
6
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2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, BX9-gene encoded protein
13
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2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one as substrate, BX9-gene encoded protein
13.4
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2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one as substrate, BX8-gene encoded protein
24
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2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one as substrate, BX8-gene encoded protein
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 10
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10% of maximal activity at pH 6.5 and 30% of maximal activity at pH 10.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
45
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 55
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88% of maximal activity at 55°C, 60% of maximal activity at 25°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
48000
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gel filtration
50000
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gel filtration, both peaks
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial, activity elutes from Q-Sepharose column in two peaks, named peak 1 and peak 2, exhibiting different activities towards substrates
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli; transfected into Arabidopsis
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