Ligand phylloquinone

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Basic Ligand Information

Molecular Structure
Picture of phylloquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C31H46O2
phylloquinone
MBWXNTAXLNYFJB-NKFFZRIASA-N
Synonyms:
2-methyl-3-phytyl-1,4-naphthoquinone, 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione, vitamin K, vitamin K1

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phylloquinone + [reduced NADPH-hemoprotein reductase] + O2 = omega-hydroxyphylloquinone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O = 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
show the reaction diagram
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vitamin K + NAD(P)H = reduced vitamin K + NAD(P)+
show the reaction diagram
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peptidyl-L-glutamate + CO2 + O2 + phylloquinone = peptidyl-4-carboxy L-glutamate + 2,3-epoxyphylloquinone + H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol = 2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol
show the reaction diagram
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S-adenosyl-L-methionine + demethylphylloquinone = S-adenosyl-L-homocysteine + phylloquinone
show the reaction diagram
-
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peptidyl-4-carboxyglutamate + 2,3-epoxyphylloquinone + H2O = peptidyl-glutamate + CO2 + O2 + phylloquinone
show the reaction diagram
-
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Substrate in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-malate + vitamin K1 = oxaloacetate + reduced vitamin K1
show the reaction diagram
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phylloquinone + [reduced NADPH-hemoprotein reductase] + O2 = omega-hydroxyphylloquinone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol + H2O = 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
show the reaction diagram
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N6-(2-isopentenyl)adenine + vitamin K1 = adenine + 3-methylbut-2-enal + reduced vitamin K1
show the reaction diagram
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NADH + phylloquinone = NAD+ + phylloquinol
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol = 2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol
show the reaction diagram
-
S-adenosyl-L-methionine + demethylphylloquinone = S-adenosyl-L-homocysteine + phylloquinone
show the reaction diagram
-
-
peptidyl-4-carboxyglutamate + 2,3-epoxyphylloquinone + H2O = peptidyl-glutamate + CO2 + O2 + phylloquinone
show the reaction diagram
-
-

Enzyme Cofactor/Cosubstrate (173 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
dependent on
-

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
with phosphate, activates purified preparation
-
dependent on
-
dependent on
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dependent on
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.015 mM, 10% inhibition
-
induction of enzyme activity
-
carboxylation of FLEEL by bovine liver carboxylase is inhibited by high concentrations of vitamin KH2. vitamin K (up to 400 mM) and vitamin K epoxide (up to 1 mM) are not inhibitory. R234A/H235A mutant, R406A/H408A mutant, and R513A/K515A mutant are more susceptible to inhibition by vitamin KH2 than wild type enzyme. R234A/H235A mutant and R406A/H408A mutant exhibit maximal activity at 111 mM vitamin KH2 and R513A/K515A mutant at 56 mM vitamin KH2
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3D Structure of Enzyme-Ligand-Complex (PDB) (52 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2.3
-
pH 6.5, recombinant enzyme

KM Value (8 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.052
-
pH 7.0

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for phylloquinone

ChEBI
PubChem
ChEBI
PubChem