Information on EC 2.6.1.36 - L-lysine 6-transaminase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.6.1.36
-
RECOMMENDED NAME
GeneOntology No.
L-lysine 6-transaminase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-lysine + 2-oxoglutarate = (S)-2-amino-6-oxohexanoate + L-glutamate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
amino group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
L-lysine degradation VI
-
-
lysine metabolism
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
L-lysine:2-oxoglutarate 6-aminotransferase
A pyridoxal-phosphate protein. The product (L-allysine) is converted into the intramolecularly dehydrated form, (S)-2,3,4,5-tetrahydropyridine-2-carboxylate.
CAS REGISTRY NUMBER
COMMENTARY hide
9054-68-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
Flavobacterium fuscum
-
-
-
Manually annotated by BRENDA team
Flavobacterium lutescens
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5-N-acetyl-L-ornithine + 2-oxoglutarate
5-(N-acetylamino)-2-oxopentanoate + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
4.0% of the activity with L-lysine
-
-
?
6-N-acetyl-L-lysine + 2-oxoglutarate
6-(N-acetylamino)-2-oxohexanoate + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
5.7% of the activity with L-lysine
-
-
?
L-alanine + 2-oxoglutarate
pyruvate + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
very slow
-
-
?
L-lysine + 2-oxoadipate
2-aminoadipate 6-semialdehyde + L-homoglutarate
show the reaction diagram
-
7% of the activity with 2-oxoglutarate
-
-
?
L-lysine + 2-oxobutanoate
2-aminoadipate 6-semialdehyde + 2-aminobutanoate
show the reaction diagram
L-lysine + 2-oxoglutarate
2-aminoadipate 6-semialdehyde + 1-piperideine-6-carboxylic acid + L-glutamate
show the reaction diagram
-
product 2-aminoadipate 6-semialdehyde is further transformed to 1-piperideine-6-carboxylic acid, which may react with methylglyoxal to generate the acylated N-heterocyclic odorant 2-acetyltetrahydropyridine
-
?
L-lysine + 2-oxoglutarate
2-aminoadipate 6-semialdehyde + ?
show the reaction diagram
-
-
-
?
L-lysine + 2-oxoglutarate
2-aminoadipate 6-semialdehyde + L-glutamate
show the reaction diagram
L-lysine + 2-oxohexanoate
2-aminoadipate 6-semialdehyde + 2-aminohexanoate
show the reaction diagram
Flavobacterium lutescens
-
8.7% of the activity with 2-oxoglutarate
-
-
?
L-lysine + 2-oxopentanoate
2-aminoadipate 6-semialdehyde + 2-aminopentanoate
show the reaction diagram
L-lysine + oxaloacetate
2-aminoadipate 6-semialdehyde + L-aspartate
show the reaction diagram
L-lysine + pyruvate
2-aminoadipate 6-semialdehyde + L-alanine
show the reaction diagram
L-lysine hydroxamate + 2-oxoglutarate
? + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
5.1% of the activity with L-lysine
-
-
?
L-ornithine + 2-oxoglutarate
5-hydroxy-L-proline + glutamate
show the reaction diagram
L-ornithine + 2-oxoglutarate
? + L-glutamate
show the reaction diagram
L-thialysine + 2-oxoglutarate
? + L-glutamate
show the reaction diagram
-
13% of the activity with L-lysine
-
-
?
N-(2'-aminoethyl)-2,3-diaminopropionate + 2-oxoglutarate
2-aminoadipate 6-semialdehyde-hydroxamate + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
3.6% of the activity with L-lysine
-
-
?
N-alpha-benzyloxycarbonyl-L-ornithine + 2-oxoglutarate
N-benzyloxycarbonyl-5-hydroxy-L-proline + glutamate
show the reaction diagram
N-alpha-tert-butoxycarbonyl-L-ornithine + 2-oxoglutarate
N-tert-butoxycarbonyl-5-hydroxy-L-proline + glutamate
show the reaction diagram
S-(2-aminoethyl)-L-cysteine + 2-oxoglutarate
? + L-glutamate
show the reaction diagram
S-(2-N-acetylaminoethyl)-L-cysteine + 2-oxoglutarate
S-(2-N-acetylaminoethyl)-2-oxopropanoic acid + L-glutamate
show the reaction diagram
Flavobacterium lutescens
-
3.3% of the activity with L-lysine
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
L-lysine + 2-oxoglutarate
2-aminoadipate 6-semialdehyde + L-glutamate
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
pyridoxamine 5'-phosphate
Flavobacterium lutescens
-
can replace pyridoxal 5'-phosphate, Km: 0.00715 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-oxopentanedioic acid
binding energy 6.48 kcal per mol
2-[methyl[(1-methylpiperidin-2-yl)methyl]amino]-1-phenylethanol
binding energy 7.23 kcal per mol
5-Aminopentanoate
Flavobacterium lutescens
-
-
5-hydroxylysine
Flavobacterium lutescens
-
DL-
acetate
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
Br-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
Cl-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
F-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
formate
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
I-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
N-([2-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-dioxo-2,3,5,6,11,11a-hexahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indol-5-yl]methyl)-2-(4-methoxyphenyl)acetamide
binding energy 10.79 kcal per mol
O-(2-aminoethyl)-DL serine
Flavobacterium lutescens
-
-
Phenylglyoxal
Flavobacterium lutescens
-
loss of activity with lysine, no effect on activity with L-alanine
Propionate
Flavobacterium lutescens
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inhibits alanine transamination and lysine transamination
additional information
Flavobacterium lutescens
-
incubation of the enzyme with L-lysine in the presence of high concentrations of phosphate gives an inactive form of the enzyme (semiapoenzyme), reactivation with pyridoxal 5'-phosphate
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetate
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
Br-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
Cl-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
F-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
formate
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
I-
Flavobacterium lutescens
-
stimulates alanine transamination, inhibits lysine transamination
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.13 - 3.8
2-oxoglutarate
1.2 - 2.8
L-lysine
2
L-ornithine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.43
2-oxoglutarate
Mycobacterium tuberculosis
P9WQ77
-
0.917
L-lysine
Mycobacterium tuberculosis
P9WQ77
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.12
pH 7.2, 37C, wild-type enzyme
1.78
pH 7.2, 37C, recombinant enzyme
18.67
Flavobacterium lutescens
-
pH 8.0, 37C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
Flavobacterium lutescens
-
substrates L-ornithine + 2-oxoglutarate
8.3 - 8.5
Flavobacterium lutescens
-
substrates lysine + 2-oxoglutarate
9
Flavobacterium lutescens
-
substrate S-(2-aminoethyl)-L-cysteine
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9.5
Flavobacterium lutescens
-
about 40% of maximum activity at pH 6 and pH 9.5, substrates ornithine + 2-oxoglutarate
7 - 10
Flavobacterium lutescens
-
pH 7: about 50% of maximum activity, pH 10: about 30% of maximum activity
7.2 - 10.2
-
about 50% of maximum activity at pH 7.2 and pH 10.2
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
48810
-
lysine epsilon-aminotransferase is a 450 amino acid protein
49890
calculated from sequence of cDNA
51300
-
gel filtration
83000
-
gel filtration
110000
Flavobacterium lutescens
-
native PAGE
116000
Flavobacterium lutescens
-
sedimentation equilibrium method
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 49890, calculated, x * 48900, SDS-PAGE
tetramer
Flavobacterium lutescens
-
1 * 24000 (A) + 1 * 28000 (B1) + 1 * 28000 (B2) + 1 * 45000-46000 (C), SDS-disc gel electrophoresis, gel filtration in presence of 6 M guanidine-HCl, equilibrium centrifugation in presence of 6 M urea
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
docking experiments based on crystal structure PDB code 2CJH in order to identify enzyme inhibitors
hanging drop vapour diffusion method in 0.1 M trisodium citrate dihydrate solution containing 0.2 M ammonium acetate and 25% PEG 4000 in the pH range 5.4-6.0
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7.5
Flavobacterium lutescens
-
55C, 5 min, stable, partially purified enzyme
637017
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
Flavobacterium lutescens
-
pH 6.0-7.5, 5 min, stable, partially purified enzyme
65
Flavobacterium lutescens
-
5 min, activated by heat treatment
75
Flavobacterium lutescens
-
5 min, inactivation
additional information
Flavobacterium lutescens
-
pyridoxal 5'-phosphate, 0.1 mM, or 2-mercaptoethanol, 0.02%, protects against heat inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
pyridoxal 5'-phosphate, 0.1 mM, or 2-mercaptoethanol, 0.02%, protects against heat inactivation
Flavobacterium lutescens
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-5C, crystalline enzyme, 0.2 M potassium phosphate buffer, pH 7.2, 50% saturation of ammonium sulfate, 0.1 mM pyridoxal 5'-phosphate, 0.01% 2-mercaptoethanol, stable for several weeks
Flavobacterium lutescens
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
lysine epsilon-aminotransferase is partially purified from a high-producing strain of Streptomyces lactamdurans
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Ni2+-IDA column chromatography and Superdex S-200 gel filtration
-
partial
Sephacryl S-200 gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Flavobacterium lutescens
-
expressed in Escherichia coli BL21-DE3
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expressed in Escherichia coli strain JM109; expression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
fusion protein of enzyme to green fluorescent protein, study of temporal and spatial distribution of enzyme
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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production of beta-lactam antibiotics
nutrition
enzyme is involved in generation of mousy off-flavors in wine. Enzymic product 2-aminoadipate 6-semialdehyde is further transformed to 1-piperideine-6-carboxylic acid, which may react with methylglyoxal to generate the acylated N-heterocyclic odorant 2-acetyltetrahydropyridine
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