Information on EC 6.3.2.11 - carnosine synthase

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The expected taxonomic range for this enzyme is: Tetrapoda

EC NUMBER
COMMENTARY hide
6.3.2.11
-
RECOMMENDED NAME
GeneOntology No.
carnosine synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + L-histidine + beta-alanine = ADP + phosphate + carnosine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
carboxamide formation
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-
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carboxylic acid amide formation
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-
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peptide synthase reaction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arginine and proline metabolism
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beta-Alanine metabolism
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carnosine biosynthesis
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Histidine metabolism
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homocarnosine biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
L-histidine:beta-alanine ligase (ADP-forming)
This enzyme was thought to form AMP [1,2], but studies with highly purified enzyme proved that it forms ADP [4]. Carnosine is a dipeptide that is present at high concentrations in skeletal muscle and the olfactory bulb of vertebrates [3]. It is also found in the skeletal muscle of some invertebrates. The enzyme can also catalyse the formation of homocarnosine from 4-aminobutanoate and L-histidine, with much lower activity [4].
CAS REGISTRY NUMBER
COMMENTARY hide
9023-61-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ATP + 1,2,4-triazole-3-Ala + beta-Ala
AMP + phosphate + beta-Ala-1,2,4-triazole-3-alanine
show the reaction diagram
ATP + 1-methylhistidine + beta-Ala
AMP + phosphate + beta-Ala-1-methylhistidine
show the reaction diagram
ATP + 2,6-diaminopimelate + beta-Ala
AMP + phosphate + beta-Ala-2,6-diaminopimelate
show the reaction diagram
-
-
-
-
ATP + 2-imidazole-3-Ala + beta-Ala
AMP + phosphate + beta-Ala-2-imidazole-3-Ala
show the reaction diagram
ATP + 2-methyl-L-His + beta-Ala
AMP + phosphate + beta-Ala-2-methyl-L-His
show the reaction diagram
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-
i.e. ophidine
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ATP + 3-methylhistidine + beta-Ala
AMP + phosphate + beta-Ala-3-methylhistidine
show the reaction diagram
ATP + 5-hydroxylysine + beta-Ala
AMP + phosphate + beta-Ala-5-hydroxylysine
show the reaction diagram
ATP + Arg + beta-Ala
AMP + phosphate + beta-Ala-Arg
show the reaction diagram
ATP + DL-2-amino-6-hydroxyoctanoate + beta-Ala
AMP + phosphate + beta-Ala-DL-2-amino-6-hydroxyoctanoate
show the reaction diagram
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-
-
-
ATP + DL-His-DL-His + beta-Ala
AMP + phosphate + beta-Ala-DL-His-DL-His
show the reaction diagram
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-
-
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ATP + L-canavanine + beta-Ala
AMP + phosphate + beta-Ala-L-canavanine
show the reaction diagram
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-
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ATP + L-His + 2,3-diaminopropanoate
AMP + phosphate + 2,3-diaminopropanoyl-L-His
show the reaction diagram
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-
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ATP + L-His + 2,4-diaminobutanoate
AMP + phosphate + 2,4-diaminobutanoyl-L-His
show the reaction diagram
ATP + L-His + 3-amino-n-butanoate
AMP + phosphate + beta-n-aminobutanoyl-L-His
show the reaction diagram
ATP + L-His + 3-aminoisobutanoate
AMP + phosphate + 3-aminoisobutanoyl-L-His
show the reaction diagram
ATP + L-His + 4-aminobutanoate
AMP + phosphate + homocarnosine
show the reaction diagram
ATP + L-His + 5-aminopentanoate
AMP + phosphate + 5-aminopentanoyl-L-His
show the reaction diagram
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ATP + L-His + 6-aminooctanoate
AMP + phosphate + 6-aminooctanoyl-L-His
show the reaction diagram
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-
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ATP + L-His + beta-Ala
ADP + phosphate + carnosine
show the reaction diagram
ATP + L-histidine + 4-aminobutanoate
ADP + phosphate + homocarnosine
show the reaction diagram
ATP + L-histidine + beta-alanine
ADP + phosphate + carnosine
show the reaction diagram
ATP + L-lysine + beta-alanine
ADP + phosphate + ?
show the reaction diagram
ATP + L-ornithine + beta-alanine
ADP + phosphate + ?
show the reaction diagram
ATP + Lys + beta-Ala
AMP + phosphate + beta-Ala-Lys
show the reaction diagram
ATP + N-pi-methylhistidine + beta-alanine
ADP + phosphate + ?
show the reaction diagram
ATP + Orn + beta-Ala
AMP + phosphate + beta-Ala-Orn
show the reaction diagram
CTP + L-His + beta-Ala
CMP + phosphate + carnosine
show the reaction diagram
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ITP + L-His + 4-aminobutanoate
IMP + phosphate + homocarnosine
show the reaction diagram
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L-histidine + beta-alanine + ATP
carnosine + AMP + diphosphate
show the reaction diagram
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-
?
additional information
?
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ATP-diphosphate exchange
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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
ATP + L-His + beta-Ala
ADP + phosphate + carnosine
show the reaction diagram
-
the concentration of histidine in muscle and plasma is high relative to its Km with muscle carnosine synthase, whereas beta-alanine exists in low concentration in muscle and has a higher Km with muscle carnosine synthase, which indicates that it is the availability of beta-alanine that is limiting to the synthesis of carnosine in skeletal muscle
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-
?
L-histidine + beta-alanine + ATP
carnosine + AMP + diphosphate
show the reaction diagram
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-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-Diaminodecane
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10 mM, 43% loss of activity
1,8-diaminooctane
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10 mM, 27% loss of activity
1-methylhistidine
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synthesis of carnosine
2-Aminoethylphosphonic acid
3-Aminopropane sulfonic acid
3-Aminopropanephosphonic acid
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3-methylhistidine
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synthesis of carnosine
5-Aminopentanoate
5-Aminopentanol
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10 mM, 11% loss of activity
6-Aminohexanol
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10 mM, 10% loss of activity
alpha-Methyl-dopa
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Aminoethanol
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10 mM, 17% loss of activity
Aminooxyacetate
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chlorpromazine
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0.1 mM stimulates, 1 mM inhibits 45%
diphosphate
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dithiothreitol
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Fe2+
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weak
iodoacetamide
K+
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10-100 mM, weak inhibition
Mo2+
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weak
n-butylamine
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10 mM, 15% loss of activity
n-Hexylamine
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10 mM, 34% loss of activity
n-octylamine
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10 mM, 58% loss of activity
Nipecotic acid
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norepinephrine
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O-Phosphoethanolamine
phosphate
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spermidine
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
chlorpromazine
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0.1 mM stimulates, 1 mM inhibits 45%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.35 - 18.2
4-aminobutanoate
0.19 - 0.57
ATP
1.01 - 1.8
beta-Ala
0.033 - 0.46
beta-Alanine
0.0166 - 0.0185
L-His
0.1 - 0.37
L-histidine
1.42 - 4.67
L-lysine
0.52 - 7.66
L-ornithine
0.39 - 24.7
N-pi-methylhistidine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05 - 0.44
4-aminobutanoate
597
0.002 - 0.032
ATP
4
1.16 - 6.03
beta-Alanine
494
0.004 - 0.055
L-histidine
349
0.0002 - 0.004
L-lysine
134
0.0001 - 0.0066
L-ornithine
192
0.0001 - 0.015
N-pi-methylhistidine
26802
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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activity in muscle is higher after exercise, which may lead to an increase of the L-carnosine levels in plasma
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3
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7.4
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carnosine synthesis
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3 - 8.5
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6.3: about 70% of maximal activity, 8.5: about 55% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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traces
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
100000
SDS-PAGE
119000
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2 * 119000, SDS-PAGE
250000
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gel filtration
430000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 100000, SDS-PAGE
dimer
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2 * 119000, SDS-PAGE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8
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stable in the range
1000
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dithiothreitol stabilizes
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most of the activity is lost upon freezing or upon dialysis with EDTA-treated cellophan tubing for several h at 0°C
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pH 7.0, 25°C, 1 h, with crystalline ribonuclease, not significantly inactivated
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10°C, as a lyophilized powder, 25% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography
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partial, using ammonium sulfate precipitation
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in HEK-293T cells