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Information on EC 6.4.1.8 - acetophenone carboxylase
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6.4.1.8 acetophenone carboxylaseIUBMB Comments
The enzyme is involved in anaerobic degradation of ethylbenzene. No activity with acetone, butanone, 4-hydroxy-acetophenone or 4-amino-acetophenone.
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Word Map
- 6.4.1.8
-
aromatoleum
- aromaticum
- acetone
- ethylbenzene
-
benzoylacetate
-
denitrifying
- bicarbonate
-
polyproline
-
s-1-phenylethanol
-
ii-like
- atpase
-
betaproteobacterium
- zn
- bal
-
petroleum
- analysis
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Reaction Schemes
2
+
+
+
+
=
2
+
2
+
Synonyms
Apc1, APC2, Apc3, Apc4, Apc5, Apcalpha, Apcbeta, Apcgamma, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Apc1
APC2
Apc3
Apc4
Apc5
Apcalpha
Apcbeta
Apcgamma
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2 ATP + acetophenone + HCO3- + H2O + H+ = 2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
acetophenone:carbon-dioxide ligase (ADP-forming)
The enzyme is involved in anaerobic degradation of ethylbenzene. No activity with acetone, butanone, 4-hydroxy-acetophenone or 4-amino-acetophenone.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 ATP + 4-acetylpyridine + HCO3- + H2O + H+
2 ADP + 2 phosphate + 2-oxo-3-(pyridin-4-yl)propanoate
2 ATP + 4-acetylpyridine + HCO3- + H2O + H+
2 ADP + 2 phosphate + 2-oxo-3-(pyridin-4-yl)propanoate
-
22% of the activity with acetophenone
-
-
?
2 ATP + 4-acetylpyridine + HCO3- + H2O + H+
2 ADP + 2 phosphate + 2-oxo-3-(pyridin-4-yl)propanoate
-
22% of the activity with acetophenone
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
-
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
anaerobic ethylbenzene metabolism in the betaproteobacterium Aromatoleum aromaticum is initiated by anaerobic oxidation to acetophenone via (S)-1-phenylethanol. The subsequent carboxylation of acetophenone to benzoylacetate is catalyzed by an acetophenone-induced enzyme
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
the enzyme shows uncoupled ATPase activity with either bicarbonate or acetophenone in the absence of the second substrate. These observations indicate that both substrates may be phosphorylated. Purified enzyme shows no activity with GTP, CTP, UTP or ITP
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
-
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
anaerobic ethylbenzene metabolism in the betaproteobacterium Aromatoleum aromaticum is initiated by anaerobic oxidation to acetophenone via (S)-1-phenylethanol. The subsequent carboxylation of acetophenone to benzoylacetate is catalyzed by an acetophenone-induced enzyme
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
the enzyme shows uncoupled ATPase activity with either bicarbonate or acetophenone in the absence of the second substrate. These observations indicate that both substrates may be phosphorylated. Purified enzyme shows no activity with GTP, CTP, UTP or ITP
-
-
?
2 ATP + propiophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 4-oxo-4-phenylbutanoate
-
108% of the activity with acetophenone
-
-
?
2 ATP + propiophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 4-oxo-4-phenylbutanoate
-
108% of the activity with acetophenone
-
-
?
additional information
?
-
-
no activity with acetone, butanone, 4-hydroxy-acetophenone or 4-amino-acetophenone
-
-
?
additional information
?
-
-
no activity with acetone, butanone, 4-hydroxy-acetophenone or 4-amino-acetophenone
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
anaerobic ethylbenzene metabolism in the betaproteobacterium Aromatoleum aromaticum is initiated by anaerobic oxidation to acetophenone via (S)-1-phenylethanol. The subsequent carboxylation of acetophenone to benzoylacetate is catalyzed by an acetophenone-induced enzyme
-
-
?
2 ATP + acetophenone + HCO3- + H2O + H+
2 ADP + 2 phosphate + 3-oxo-3-phenylpropanoate
-
anaerobic ethylbenzene metabolism in the betaproteobacterium Aromatoleum aromaticum is initiated by anaerobic oxidation to acetophenone via (S)-1-phenylethanol. The subsequent carboxylation of acetophenone to benzoylacetate is catalyzed by an acetophenone-induced enzyme
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Zn2+
-
the enzyme contains 1 Zn2+ ion per alphabetagammadelta core complex. In spite of the presence of Zn in the enzyme, it is strongly inhibited by Zn2+ ions
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
beta,gamma-Imido-ATP
-
2 mM, complete inhibition of acetophenone carboxylase activity, non-competitive inhibition
Carbamoyl phosphate
-
2 mM: 50% inhibition of ATPase activity. 8 mM: 50% inhibition of carboxylating activity
Ni2+
-
1 mM: 50% inhibition of ATPase activity. 2.5 mM: 50% inhibition of carboxylation activity
Zn2+
-
the enzyme contains 1 Zn2+ ion per alphabetagammadelta core complex. In spite of the presence of Zn in the enzyme, it is strongly inhibited by Zn2+ ions. 0.2 mM ZnCl2: 50% inhibition of ATPase activity and carboxylation activity
additional information
-
acetophenone carboxylation activity in cell extracts is not sensitive to avidin, indicating that the enzyme is independent of biotin
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Q5P5G2 i.e. alpha-subunit, Q5P5G3 i.e. beta-subunit, Q5P5G4 i.e. gamma-subunit, Q5P5G5 i.e. delta-subunit, Q5P5G6 i.e. epsilon-subunit
UniProt
brenda
Show AA Sequence and Transmembrane Helices (1418 entries)
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
15000
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
34000
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
70000
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
75000
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
87000
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pentamer
pentamer
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
pentamer
-
1 * 70000 (alpha) + 1 * 15000 (beta) + 1 * 87000 (gamma) + 1 * 75000 (delta) + 1 * 34000 (epsilon), the genes (apcABCDE) of the five subunits form an apparent operon
-
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
structure of the Apc(alphaalpha'betagamma)2 core complex, to 3.0 A resolution. Subunit Apcbeta contains a domain fold composed of two beta-sheets in a barrel-like arrangement running into a bundle of eight short polyproline (type II)-like helical segments. Apcalpha and Apcalpha' possess ATP-binding modules of the ASKHA superfamily and presumably operate as ATP-dependent kinases for acetophenone and bicarbonate, respectively
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
during purification, acetophenone carboxylase dissociates into inactive subcomplexes consisting of the 70-, 15-, 87-, and 75-kDa subunits (apcABCD gene products) and the 34-kDa subunit (apcE gene product), respectively. Acetophenone carboxylase activity is restored by mixing the purified subcomplexes
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
heterologous expression of the apcEC-His6 subunit in Escherichia coli
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
acetophenone carboxylase is formed in ethylbenzene- and toluene-adapted cells
expression of alpha-subunit is proportional to the applied acetophenone concentrations
the enzyme is synthesized at high levels in cells grown on ethylbenzene or acetophenone, but not in cells grown on benzoate
acetophenone carboxylase is formed in ethylbenzene- and toluene-adapted cells
-
acetophenone carboxylase is formed in ethylbenzene- and toluene-adapted cells
-
-
expression of alpha-subunit is proportional to the applied acetophenone concentrations
expression of alpha-subunit is proportional to the applied acetophenone concentrations
-
-
the enzyme is synthesized at high levels in cells grown on ethylbenzene or acetophenone, but not in cells grown on benzoate
-
the enzyme is synthesized at high levels in cells grown on ethylbenzene or acetophenone, but not in cells grown on benzoate
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
analysis
construction of a reporter strain by inserting a gene fusion of apcA, the first gene of the apc-bal operon, with the gene for the fluorescent protein mCherry into the chromosome. mCherry production is proportional to the applied acetophenone concentrations. The reporter strain allows quantification of acetophenone within a concentration range of 50 microM (detection limit) to 250 microM after 12 and 24 h. Production of the Apc-mCherry fusion protein in the reporter strain is highly specific and responds to acetophenone and both enantiomers of 1-phenylethanol
analysis
-
construction of a reporter strain by inserting a gene fusion of apcA, the first gene of the apc-bal operon, with the gene for the fluorescent protein mCherry into the chromosome. mCherry production is proportional to the applied acetophenone concentrations. The reporter strain allows quantification of acetophenone within a concentration range of 50 microM (detection limit) to 250 microM after 12 and 24 h. Production of the Apc-mCherry fusion protein in the reporter strain is highly specific and responds to acetophenone and both enantiomers of 1-phenylethanol
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kuhner, S.; Wohlbrand, L.; Fritz, I.; Wruck, W.; Hultschig, C.; Hufnagel, P.; Kube, M.; Reinhardt, R.; Rabus, R.
Substrate-dependent regulation of anaerobic degradation pathways for toluene and ethylbenzene in a denitrifying bacterium, strain EbN1
J. Bacteriol.
187
1493-1503
2005
Aromatoleum aromaticum, Aromatoleum aromaticum EbN1
brenda
Jobst, B.; Schühle, K.; Linne, U.; Heider, J.
ATP-dependent carboxylation of acetophenone by a novel type of carboxylase
J. Bacteriol.
192
1387-1394
2010
Aromatoleum aromaticum, Aromatoleum aromaticum EbN1
brenda
Muhr, E.; Leicht, O.; Sierra, S.; Thanbichler, M.; Heider, J.
A fluorescent bioreporter for acetophenone and 1-phenylethanol derived from a specifically induced catabolic operon
Front. Microbiol.
6
1561
2016
Aromatoleum aromaticum (Q5P5G2 and Q5P5G3 and Q5P5G4 and Q5P5G5 and Q5P5G6), Aromatoleum aromaticum, Aromatoleum aromaticum EbN1 (Q5P5G2 and Q5P5G3 and Q5P5G4 and Q5P5G5 and Q5P5G6)
brenda
Weidenweber, S.; Schuehle, K.; Demmer, U.; Warkentin, E.; Ermler, U.; Heider, J.
Structure of the acetophenone carboxylase core complex prototype of a new class of ATP-dependent carboxylases/hydrolases
Sci. Rep.
7
39674
2017
Aromatoleum aromaticum (Q5P5G2 and Q5P5G3 and Q5P5G4 and Q5P5G5 and Q5P5G6), Aromatoleum aromaticum, Aromatoleum aromaticum EbN1 (Q5P5G2 and Q5P5G3 and Q5P5G4 and Q5P5G5 and Q5P5G6)
brenda
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