Information on EC 2.3.3.9 - malate synthase

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

EC NUMBER
COMMENTARY hide
2.3.3.9
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RECOMMENDED NAME
GeneOntology No.
malate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + glyoxylate + H2O = (S)-malate + CoA
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aldol condensation
-
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Claisen condensation
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chitin degradation to ethanol
-
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glycolate and glyoxylate degradation II
-
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glyoxylate cycle
-
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L-arabinose degradation IV
-
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methylaspartate cycle
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TCA cycle IV (2-oxoglutarate decarboxylase)
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TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase)
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xylose degradation IV
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citric acid cycle
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Pyruvate metabolism
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Glyoxylate and dicarboxylate metabolism
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Metabolic pathways
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Biosynthesis of secondary metabolites
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:glyoxylate C-acetyltransferase (thioester-hydrolysing, carboxymethyl-forming)
The enzyme catalyses the irreversible condensation of acetyl-CoA with glyoxylate to form (S)-malate. Among other functions, the enzyme participates in the glyoxylate cycle, a modified version of the TCA cycle that bypasses steps that lead to a loss of CO2.
CAS REGISTRY NUMBER
COMMENTARY hide
9013-48-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
thermophilic
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
Candida tropicalis pK 233
pK 233
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Cucurbita sp.
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
sunflower
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
strain Pb01
UniProt
Manually annotated by BRENDA team
Paracoccidioides sp.
Paracoccidioides sp. ATCC MYA-826
isolate Pb01
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
NRRL3585
SwissProt
Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + glyoxylate + H2O
(S)-malate + CoA
show the reaction diagram
acetyl-CoA + glyoxylate + H2O
CoA + (S)-malate
show the reaction diagram
acetyl-CoA + H2O + glyoxylate
(S)-malate + CoA
show the reaction diagram
glyoxylate + acetyl-CoA + H2O
(S)-malate + CoA
show the reaction diagram
glyoxylate + butyryl-CoA + H2O
2-oxohexanedioic acid + CoA
show the reaction diagram
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ir
glyoxylate + fluoroacetyl-CoA + H2O
2-oxo-3-fluoro-butanedioic acid + CoA
show the reaction diagram
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ir
glyoxylate + propionyl-CoA + H2O
2-oxopentanedioic acid + CoA
show the reaction diagram
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-
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ir
additional information
?
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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
acetyl-CoA + H2O + glyoxylate
(S)-malate + CoA
show the reaction diagram
glyoxylate + acetyl-CoA + H2O
(S)-malate + CoA
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
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about 30% of the activation with Mg2+
KCl
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salt optimum: 3.0 M KCl
Ni2+
-
about 98% of the activation with Mg2+
additional information
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Co2+, Fe2+, Ca2+, Ba2+, Ni2+, Cd2+, Zn2+, Cu2+, Hg2+ are not able to support the activity of enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1S,2S,3R)-2-(5-methoxy-9H-b-carbolin-1-yl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol
Paracoccidioides sp.
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16-ethenyl-21-oxo-19,20-didehydro-18-oxayohimban-17-yl hexopyranoside
Paracoccidioides sp.
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2,4,5-trioxopyrrolidine-3-carboxamide
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; competitive
3-ethenyl-2-(5-methoxy-9H-b-carbolin-1-yl)-1-methylcyclopentanol
Paracoccidioides sp.
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9-(hydroxymethyl)-8-methyl-8,9,10,11,11a,12-hexahydro-6H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizin-13-yl acetate
Paracoccidioides sp.
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acetaldehyde
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weak
acetyl-CoA
Bromopyruvate
Butanedione
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slight inhibition at high concentrations
Ca2+
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5 mM, 19% residual activity
Chloroacetyl-CoA
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citrate
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1 mM, 82% residual activity
coenzyme A
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0.1 mM, 56% residual activity
D-fructose-1,6-bisphosphate
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10 mM, 60% residual activity
deamino-acetyl-CoA
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deoxycholate
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dephosphoacetyl-CoA
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dethio-CoA
uncompetitive inhibitor versus glyoxylate and competitive inhibitor versus acetyl-CoA
diethyl dicarbonate
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inhibition prevented by preincubation with acetyl-CoA
EDTA
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1.0 mM, 30% inhibition
fluoroacetate
glycolate
Glyoxal
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10 mM, 70% residual activity
glyoxylate
iodoacetate
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5 mM, 6% residual activity
K+
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5 mM, 5% residual activity
malate
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1.0 mM, 50% inhibition
methyl 13-amino-2,11-dimethoxy-3-[(3,4,5-trimethoxybenzoyl)oxy]-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindeno[2',1':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
Paracoccidioides sp.
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methylglyoxal
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Mn2+
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5 mM, 16% residual activity
Na+
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5 mM, 10% residual activity
oxalate
oxaloacetate
p-chloromercuribenzoate
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0.05 mM, 9% residual activity
parabanic acid
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; competitive
phosphoenolpyruvate
pyridoxal-5'-phosphate
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preincubation with glyoxylate but not acetyl-CoA prevents inhibition
pyruvate
S-Acetonyl-CoA
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S-Ethyl-CoA
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additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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0.01 mM, 10% activation
Triton X-100
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activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00012 - 0.11
acetyl-CoA
0.045
glyoxalate
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pH 8.0, 30C
0.00011 - 2
glyoxylate
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
23 - 161
acetyl-CoA
3.19 - 48.1
glyoxylate
additional information
additional information
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04 - 0.113
2,4,5-trioxopyrrolidine-3-carboxamide
0.01 - 4.3
ATP
0.06
Bromopyruvate
0.246
fluoroacetate
0.07 - 0.9
glycolate
0.019 - 1.5
oxalate
1.5
oxaloacetate
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-
0.37 - 0.55
parabanic acid
0.2
phosphoenolpyruvate
0.54 - 1.6
pyruvate
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.05
(1S,2S,3R)-2-(5-methoxy-9H-b-carbolin-1-yl)-1-methyl-3-(prop-1-en-2-yl)cyclopentanol
Paracoccidioides sp.
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at pH 7.0 and 35C
additional information
16-ethenyl-21-oxo-19,20-didehydro-18-oxayohimban-17-yl hexopyranoside
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.39
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mutant R338K, pH 8.0, 37C
3.73
cells grown in the presence of potassium acetate
5.19
30C, pH 8.0
6
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recombinant enzyme
15.6
mutant D453A, pH 7.9
24.5
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26.9
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wild-type enzyme
27
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mutant enzyme PC2 NG35
31.8
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mutant C617S, pH 8.0, 37C
36.1
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wild-type, pH 8.0, 37C
44.2
mutant R171L, pH 7.9
25090
wild-type, pH 7.9
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.2
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phosphate-citrate-borate buffer or MOPS-KOH buffer
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9.5
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pH 5.0: about 35% of maximal activity, pH 9.5: about 70% of maximal activity
6.8 - 9.7
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pH 6.8 and 9.7: about 50% of maximal activity, phosphate-citrate-borate buffer
7 - 10
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pH 7.0: about 40% of maximal activity, pH 10.0: about 45% of maximal activity
7 - 8.5
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pH 7.0: about 80% of maximal activity, pH 8.7: about 60% of maximal activity, enzyme form MSL and MSH
7.5 - 8.5
malate synthase reaction
7.5 - 10.5
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pH 7.5: about 55% of maximal activity, pH 10.5: about 25% of maximal activity, enzyme form MSL and MSH
8 - 10
10
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85% activity
additional information
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below pH 6: no activity remains, outside pH 7-10 the activity decreases rapidly
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5
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15.5% activity
15
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47.1% activity
20 - 45
25 - 80
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25C: about 45% of maximal activity, 80C: about 45% of maximal activity
32.5 - 40
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more than 90% of activity
additional information
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Km for glyoxylate increases with decreasing temperature
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
animal
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Automatic Mining of ENzyme DAta
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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abundant in ehtanol-grown cells
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Haloferax volcanii (strain ATCC 29605 / DSM 3757 / JCM 8879 / NBRC 14742 / NCIMB 2012 / VKM B-1768 / DS2)
Haloferax volcanii (strain ATCC 29605 / DSM 3757 / JCM 8879 / NBRC 14742 / NCIMB 2012 / VKM B-1768 / DS2)
Haloferax volcanii (strain ATCC 29605 / DSM 3757 / JCM 8879 / NBRC 14742 / NCIMB 2012 / VKM B-1768 / DS2)
Haloferax volcanii (strain ATCC 29605 / DSM 3757 / JCM 8879 / NBRC 14742 / NCIMB 2012 / VKM B-1768 / DS2)
Mycobacterium leprae (strain Br4923)
Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)
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)
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)
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)
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)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
52000 - 54000
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gel filtration, equilibrum sedimentation centrifugation, light scattering, two distinct forms of enzyme
55000
-
gel filtration
65000
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gel filtration, enzyme form MSL
110000
-
gel filtration
120000
Cucurbita sp.
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sucrose density gradient centrifugation
160000
170000
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gel filtration, ultracentrifugation, sucrose density gradient centrifugation
180000
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high speed equilibrium sedimentation
186000
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small-angle X-ray scattering technique
200000
-
gel filtration