Ligand methyl-alpha-D-glucoside

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Basic Ligand Information

Molecular Structure
Picture of methyl-alpha-D-glucoside (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H14O6
methyl-alpha-D-glucoside
HOVAGTYPODGVJG-ZFYZTMLRSA-N
Synonyms:
1-methyl-alpha-glucopyranoside, 1-O-methyl-alpha-D-glucopyranose, 1-O-methyl-alpha-D-glucose, 1-O-methyl-alpha-D-glucosylpyranoside, alpha-D-methyl-glucoside, alpha-D-methylglucopyranose, alpha-methyl-D-glucose, alpha-methyl-D-glucoside, alpha-methyl-glucoside, alpha-methylglucose, alpha-methyl glucoside, alpha-methylglucoside, methyl-alpha-D-glucopyranose, methyl-alpha-D-glucopyranoside, methyl-alpha-D-glucose, methyl-alpha-glucoside, methyl alpha-D-glucopyranoside, methyl alpha-D-glucose 6-phosphate[side 2], methyl alpha-D-glucoside, methyl alpha-D-glucoside[side 1], methyl alpha-glucopyranoside, methyl alpha-glucoside, methyl alpha-glucoside[side 1]

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[protein]-Npi-phospho-L-histidine + methyl alpha-D-glucoside[side 1] = [protein]-L-histidine + methyl alpha-D-glucose 6-phosphate[side 2]
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[protein]-Npi-phospho-L-histidine + methyl alpha-D-glucoside[side 1] = [protein]-L-histidine + methyl alpha-D-glucose 6-phosphate[side 2]
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
methyl alpha-D-glucoside + O2 = 2-dehydro-alpha-D-methylglucoside + H2O2
show the reaction diagram
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alpha-methyl-D-glucoside + O2 + H2O = ? + H2O2
show the reaction diagram
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1-O-methyl-alpha-D-glucosylpyranoside + O2 = 1-O-methyl-alpha-D-gluco-hexodialdose + H2O2
show the reaction diagram
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methyl-alpha-D-glucopyranoside + 2,6-dichlorophenolindophenol = ? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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acetyl-CoA + methyl alpha-D-glucopyranoside = CoA + methyl 6-O-acetyl-alpha-D-glucopyranoside
show the reaction diagram
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sucrose + methyl-alpha-D-glucoside = oligoalternan
show the reaction diagram
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methyl-alpha-D-glucoside + starch = methyl-alpha-isomaltoside + ?
show the reaction diagram
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alpha-D-glucose 1-phosphate + methyl alpha-D-glucoside = ? + phosphate
show the reaction diagram
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UDPgalactose + alpha-methyl-D-glucose = ?
show the reaction diagram
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starch + methyl-alpha-D-glucoside = ?
show the reaction diagram
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methyl alpha-D-glucoside + alpha-D-mannose 1-phosphate = methyl [4-O-beta-D-mannopyranosyl]-alpha-D-glucoside + phosphate
show the reaction diagram
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methyl alpha-D-glucoside + beta-D-glucose 1-phosphate = methyl 4-O-alpha-D-glucopyranosyl-alpha-D-glucopyranoside + phosphate
show the reaction diagram
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methyl alpha-D-glucopyranoside + vinyl acetate = ? + vinyl alcohol
show the reaction diagram
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methyl alpha-D-glucopyranoside + H2O = methanol + alpha-D-glucopyranose
show the reaction diagram
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methyl-alpha-D-glucoside + H2O = methanol + alpha-D-glucose
show the reaction diagram
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p-nitrophenyl 6-O-sulfo-N-acetyl-beta-D-glucosaminide + methyl alpha-D-glucopyranoside = methyl 4-O-[2-(acetylamino)-2-deoxy-6-O-sulfo-beta-D-glucopyranosyl]-alpha-D-glucopyranoside + 4-nitrophenol
show the reaction diagram
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alpha-Methyl-D-glucoside + alpha-D-glucose 1-phosphate = alpha-Methyl-D-glucoside 6-phosphate + D-glucose
show the reaction diagram
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methyl alpha-D-glucoside = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[protein]-Npi-phospho-L-histidine + methyl alpha-D-glucoside[side 1] = [protein]-L-histidine + methyl alpha-D-glucose 6-phosphate[side 2]
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50 mM, activates release of D-fructose, sucrase activity, inhibits synthesis of dextran, transferase activity
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Inhibitor in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
weak
-
E 192, 80% inhibition
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competitive inhibition
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23% inhibition at 10 mM
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50 mM, 20% inhibition
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with glycogen as substrate
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (10 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
6
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mutant N156D/N163D/T508I/E649G/N667A, pH 6.6, 37°C
8.3
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pH 7.0, 30°C, reverse phosphorolysis, donor beta-D-glucopyranose 1-phosphate
20.7
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apparent value, pH 6.5, 37°C, synthetic reaction, cosubstrate alpha-D-mannose 1-phosphate
0.957
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pH 8.0, 37°C

KM Value (20 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1009
-
mutant N156D/N163D/T508I/E649G/N667A, pH 6.6, 37°C
79
-
pH 7.0, 30°C, reverse phosphorolysis, donor beta-D-glucopyranose 1-phosphate
85.3
-
apparent value, pH 6.5, 37°C, synthetic reaction, cosubstrate alpha-D-mannose 1-phosphate
16.3
-
pH 8.0, 37°C
0.006
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at pH 7.5, temperature not specified in the publication

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.37
-
pH and temperature not specified in the publication
0.0349
-
solubilized isoform EIICBAGlc2, at pH 7.5 and 37°C
89
-
pH 6.0, 30°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0008
-
at pH 7.5 and 30°C

References & Links

Links to other databases for methyl-alpha-D-glucoside

ChEBI
PubChem
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PubChem