Ligand 4-hydroxyphenyl-alpha-D-glucopyranoside

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxyphenyl-alpha-D-glucopyranoside (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C12H16O7
4-hydroxyphenyl-alpha-D-glucopyranoside
BJRNKVDFDLYUGJ-ZIQFBCGOSA-N
Synonyms:
alpha-arbutin, hydroquinone-O-alpha-D-glucopyranoside

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
alpha-arbutin + O2 = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
sucrose + hydroquinone = D-fructose + 4-hydroxyphenyl-alpha-D-glucopyranoside
show the reaction diagram
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sucrose + hydroquinone = D-fructose + alpha-arbutin
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition of monophenolase activity, the inhibitory activity of beta-arbutin is higher compared to alpha-arbutin, molecular docking, overview. The hydroxyl group establishes hydrogen bonds with the peroxide ion and polar contacts with a copper ion as well as with residues H259 and H263. The aromatic ring position cannot be stabilized by Pi-Pi-interactions
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.43
-
pH 7.0, 25C

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
6.5
-
pH 7.0, 25C

References & Links

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

ChEBI
PubChem
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PubChem