Ligand 4-nitrophenyl alpha-D-glucopyranoside

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Basic Ligand Information

Molecular Structure
Picture of 4-nitrophenyl alpha-D-glucopyranoside (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C12H15NO8
4-nitrophenyl alpha-D-glucopyranoside
IFBHRQDFSNCLOZ-ZIQFBCGOSA-N
Synonyms:
4-nitophenyl-alpha-D-glucopyranoside, 4-nitrophenyl-alpha-D-glucopyranoside, 4-nitrophenyl-alpha-D-glucoside, 4-nitrophenyl 1-O-alpha-D-glucopyranoside, 4-nitrophenyl alpha-D-glucoside, 4-nitrophenyl alpha-glucopyranoside, 4-nitrophenyl D-alpha-glucopyranoside, p-nitropenyl-D-alpha-glucopyranoside, p-nitrophenyl-alpha-D-glucopyranoside, p-nitrophenyl-alpha-D-glucose, p-nitrophenyl-alpha-D-glucoside, p-Nitrophenyl-alpha-glucoside, p-nitrophenyl alpha-D-glucopyranoside, p-nitrophenyl alpha-D-glucoside, p-nitrophenyl alpha-glucoside

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (73 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-nitrophenyl alpha-D-glucoside + acceptor = p-nitrophenyl-3-dehydro-alpha-D-glucoside + reduced acceptor
show the reaction diagram
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acetyl-CoA + 4-nitrophenyl alpha-D-glucopyranoside = CoA + 4-nitrophenyl 6-O-acetyl-alpha-D-glucopyranoside
show the reaction diagram
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4-nitrophenyl-alpha-D-glucopyranoside + H2O = 4-nitrophenol + alpha-D-glucopyranose
show the reaction diagram
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4-nitrophenyl D-alpha-glucopyranoside + H2O = 4-nitrophenol + D-glucose
show the reaction diagram
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H2O + p-nitrophenyl-alpha-D-glucoside = alpha-D-glucose + p-nitrophenol
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4-nitrophenyl alpha-D-glucoside + H2O = 4-nitrophenol + alpha-D-glucose
show the reaction diagram
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4-nitrophenyl alpha-D-glucopyranoside + H2O = 4-nitrophenol + beta-D-glucose
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p-nitrophenyl alpha-D-glucopyranoside + H2O = p-nitrophenol + D-glucose
show the reaction diagram
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4-nitrophenyl alpha-D-glucoside + H2O = 4-nitrophenol + D-glucose
show the reaction diagram
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4-nitrophenyl alpha-D-glucopyranoside + H2O = 4-nitrophenol + alpha-D-glucopyranose
show the reaction diagram
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4-nitrophenyl-alpha-D-glucopyranoside + 4-nitrophenyl 6-O-sulfo-N-acetyl-beta-D-glucosaminide = 4-nitrophenyl-[6-O-sulfo-beta-D-glucopyranosyl]-2-alpha-D-glucopyranoside + 4-nitrophenol
show the reaction diagram
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4-nitrophenyl alpha-D-glucopyranoside + H2O = 4-nitrophenol + D-glucose
show the reaction diagram
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4-nitrophenyl alpha-D-glucoside + H2O = 4-nitrophenol + alpha-D-glucose
show the reaction diagram
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4-nitrophenyl alpha-D-glucopyranoside + H2O = 4-nitrophenol + D-glucose
show the reaction diagram
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transferrin + 4-nitrophenyl-alpha-D-glucoside = ?
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maltoheptaose + p-nitrophenyl alpha-glucoside = p-nitrophenyl alpha-maltoheptaoside + D-glucose
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4-nitrophenyl alpha-D-glucopyranoside = ?
show the reaction diagram
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4-nitrophenyl alpha-D-glucoside = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-nitrophenyl alpha-maltoside + H2O = 4-nitrophenyl alpha-D-glucoside + D-glucose
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
E 192, 55% inhibition
-
inhibitor of isoform EIICBAGlc2
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48.6% inhibition at 15 mM
competitive inhibitor, inhibits both sucrase and isomaltase
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (46 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.046
-
pH 7.0, 37°C
0.25
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wild-type enzyme

KM Value (116 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
7.7
-
pH 7.0, 37°C
0.29
-
at pH 4.6 and 50°C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0321
-
solubilized isoform EIICBAGlc2, at pH 7.5 and 37°C

References & Links

Links to other databases for 4-nitrophenyl alpha-D-glucopyranoside

ChEBI
PubChem
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PubChem