Information on EC 2.1.1.241 - 2,4,7-trihydroxy-1,4-benzoxazin-3-one-glucoside 7-O-methyltransferase

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The expected taxonomic range for this enzyme is: Zea mays

EC NUMBER
COMMENTARY hide
2.1.1.241
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RECOMMENDED NAME
GeneOntology No.
2,4,7-trihydroxy-1,4-benzoxazin-3-one-glucoside 7-O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + (2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside = S-adenosyl-L-homocysteine + (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
DIMBOA-glucoside biosynthesis
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Benzoxazinoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:(2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside 7-O-methyltransferase
The enzyme is involved in the biosynthesis of the protective and allelophatic benzoxazinoid DIMBOA [(2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin] in some plants, most commonly from the family of Poaceae (grasses).
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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Bx7 catalyzes the last step in benzoxazinoid biosynthesis of maize
physiological function
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Bx7 is required for biosynthesis of the benzoxazinoid pesticide 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, i.e. DIMBOA, that is synthesized in seedlings and stored as glucoside in maize
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + (2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
S-adenosyl-L-homocysteine + (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
show the reaction diagram
additional information
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the only substance that serves as a substrate for the recombinant Bx7 is TRIBOA-Glc, neither the aglucone TRIBOA nor well-known substrates of plant O-methyltransferases are efficiently converted by the enzyme. In case of quercetin, a minor activity is detected. BX7 has no catalytic activity toward phenylpropanoids and flavonoids, e.g. apigenin is no substrate
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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
S-adenosyl-L-methionine + (2R)-4,7-dihydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
S-adenosyl-L-homocysteine + (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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Mg2+ is not required for catalysis
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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1 mM Mg2+, 1 mM EDTA, 5% ethanol, or 6% DMSO have no effect on BX7 activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
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steady-state kinetic constants of BX7
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Bx7 is highest expressed in seedling tissue
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 40000, native enzyme, SDS-PAGE
additional information
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peptide mapping by mass spectrometry
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, Bx7 maps to the cluster of Bx genes on the short arm of chromosome 4, Bx7 is located 9 cM distal to the marker adh2 at position 47, phylogenetic analysis, expression as His-tagged enzyme in Escherichia coli
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