Ligand L-norleucine

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Basic Ligand Information

Molecular Structure
Picture of L-norleucine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H13NO2
L-norleucine
LRQKBLKVPFOOQJ-YFKPBYRVSA-N
Synonyms:
(2S)-2-aminohexanoate, (S)-norleucine, L-2-aminohexanoate, L-2-aminohexanoic acid, L-Nle, norleucine

Roles as Enzyme Ligand

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

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + norleucine = CoA + N-acetyl-D-norleucine
show the reaction diagram
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L-norleucine + 2-oxoglutarate = 2-oxohexanoate + L-glutamate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (42 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-norleucine + O2 = ? + NH3 + H2O2
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L-norleucine + 2-oxoglutarate + O2 = 4-hydroxy-L-norleucine + succinate + CO2
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L-norleucine + H2O + NADH + H+ = 2-oxohexanoate + NH3 + NAD+
show the reaction diagram
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L-norleucine + H2O + NAD+ = 2-oxocaproate + NADH + NH3
show the reaction diagram
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L-norleucine + H2O + 2 cytochrome b = 2-oxohexanoate + NH3 + 2 reduced cytochrome b
show the reaction diagram
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(S)-Norleucine + pyruvate + NADH = N-[1-(R)-(Carboxy)ethyl]-norleucine + NAD+
show the reaction diagram
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acetyl-CoA + norleucine = CoA + N-acetyl-D-norleucine
show the reaction diagram
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pyruvate + L-norleucine = L-alanine + 2-oxohexanoate
show the reaction diagram
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2-oxosuccinamic acid + L-norleucine = L-asparagine + 2-oxohexanoate
show the reaction diagram
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phenylpyruvate + L-norleucine = phenylalanine + 2-oxohexanoate
show the reaction diagram
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L-norleucine + 2-oxoglutarate = 2-oxohexanoate + L-glutamate
show the reaction diagram
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L-norleucine + 2-oxoglutarate = 2-oxohexanoate + L-glutamate
show the reaction diagram
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L-norleucine + phenylpyruvate = 2-oxohexanoate + L-phenylalanine
show the reaction diagram
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L-norleucine + 2-oxoglutarate = 2-oxohexanoate + L-glutamate
show the reaction diagram
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L-norleucine + 2-oxoglutarate = 2-oxohexanoate + L-glutamate
show the reaction diagram
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L-Norleucine = Pentylamine + CO2
show the reaction diagram
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2-Oxobutanoate + L-norleucine = ?
show the reaction diagram
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L-norleucine = ?
show the reaction diagram
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L-Norleucine = D-Norleucine
show the reaction diagram
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L-Norleucine = D-Norleucine
show the reaction diagram
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ATP + L-norleucine + tRNAMet = AMP + diphosphate + L-norleucyl-tRNAMet
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ATP + L-Glu + L-norleucine = ADP + phosphate + gamma-L-Glu-L-norleucine
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (34 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxohexanoate + NH3 + NADH + H+ = L-norleucine + H2O + NAD+
show the reaction diagram
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N-methyl-L-norleucine + O2 + H2O = L-norleucine + formaldehyde + H2O2
show the reaction diagram
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beta-alanine + 2-oxohexanoate = malonic semialdehyde + L-norleucine
show the reaction diagram
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histidine + 2-oxocaproate = imidazol-5-yl-pyruvate + L-norleucine
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L-tyrosine + 2-oxohexanoate = 3-(4-hydroxyphenyl)-2-oxopropanoate + (2S)-2-aminohexanoate
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L-glutamine + 2-oxocaproate = 2-oxoglutaramate + L-norleucine
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L-kynurenine + 2-oxohexanoate = kynurenic acid + L-norleucine + H2O
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norleucinamide + H2O = norleucine + NH3
show the reaction diagram
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Nle-Gly-Met-Phe + H2O = Gly-Met-Phe + norleucine
show the reaction diagram
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L-Nle-7-amido-4-carbamoylmethylcoumarin + H2O = L-Nle + 7-amino-4-carbamoylmethylcoumarin
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norleucyl-7-amido-4-methylcoumarin + H2O = norleucine + 7-amino-4-methylcoumarin
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L-Nle-Pro-7-amido-4-carbamoylmethylcoumarin + H2O = L-Nle + Pro-7-amido-4-carbamoylmethylcoumarin
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norleucyl-Ala + H2O = norleucine + Ala
show the reaction diagram
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DL-alpha-amino-n-capronitrile + H2O = L-norleucine + NH3
show the reaction diagram
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D-norleucine = L-norleucine
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, 2.05fold activation
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Inhibitor in Enzyme-catalyzed Reactions (15 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition 20% by 10 mM L-norleucine
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pH 7.6, 30°C
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30 mM, weak
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product inhibition
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inhibits PSA
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L-methionine analogue, competitive
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3D Structure of Enzyme-Ligand-Complex (PDB) (256 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (13 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
17.9
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pH 10.0, 21°C
17.9
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260
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half transamination reaction, pH 8.0, 90°C
61
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pH 6.6, 55°C
0.102
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pH 7.5, 37°C, recombinant enzyme
2.15
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ATP-diphosphate exchange reaction, pH 7.6

KM Value (35 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.83
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calculation from oxygen consumption due to oxidation and/or oxygenation
3.72
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pyruvate and NADH as cosubstrates
3.4
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with phenylpyruvate, pH 8.0, 30°C
1.8
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pH 7.8, 35°C, in the presence of 2-oxoglutarate
1.07
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pH 7.5, 37°C, recombinant enzyme

Ki Value (3 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.91
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pH 7.6, 30°C

References & Links

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Links to other databases for L-norleucine

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ChEBI
PubChem
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PubChem