Ligand phenylacetonitrile

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Basic Ligand Information

Molecular Structure
Picture of phenylacetonitrile (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H7N
phenylacetonitrile
SUSQOBVLVYHIEX-UHFFFAOYSA-N
Synonyms:
(Z)-phenylacetnitrile, 2-phenylacetonitrile, arylacetonitrile, benzene acetonitrile, benzeneacetonitrile, benzylcyanide, benzyl cyanide, phenyl acetonitrile

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
phenylacetonitrile + 2 H2O = phenylacetate + NH3
show the reaction diagram
-
phenylacetonitrile + 2 H2O = phenylacetic acid + NH3
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O
show the reaction diagram
-
-
(Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzyl cyanide + NADH + H+ + O2 = cis-1,2-dihydroxy-3,5-cyclohexadienyl acetonitrile + NAD+
show the reaction diagram
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phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-hydroxy-2-phenylethanimine + [reduced NADPH-hemoprotein reductase] + O2 = phenylacetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
(Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O
show the reaction diagram
-
-
(Z)-phenylacetaldoxime = phenylacetonitrile + H2O
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
absolutely required as growth nitrogen source substrate for induction of the enzyme, cannot be substituted by ammonia or epsilon-caprolactam
-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
reversible inhibitor
-
50% inhibition at 10 mM
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.4
-
pH 7.6, 30°C
3.07
-
pH 6.0, 20°C

KM Value (15 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0185
-
pH 7.6, 30°C
0.0092
-
pH 6.0, 20°C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
10
-
-

References & Links

Links to other databases for phenylacetonitrile

ChEBI
PubChem
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PubChem