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EC Tree
IUBMB Comments This enzyme is responsible for the chain-elongation step of dissociated (type II) fatty-acid biosynthesis, i.e. the addition of two C atoms to the fatty-acid chain. Escherichia coli mutants that lack this enzyme are deficient in unsaturated fatty acids. The enzyme can use fatty acyl thioesters of ACP (C2 to C16) as substrates, as well as fatty acyl thioesters of Co-A (C4 to C16) . The substrate specificity is very similar to that of EC 2.3.1.179, beta-ketoacyl-ACP synthase II, with the exception that the latter enzyme is far more active with palmitoleoyl-ACP (C16Delta9) as substrate, allowing the organism to regulate its fatty-acid composition with changes in temperature [4,5].
The taxonomic range for the selected organisms is: Homo sapiens The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
condensing enzyme, beta-ketoacyl synthase, kas i, beta-ketoacyl-acp synthase, beta-ketoacyl synthetase, 3-ketoacyl-acyl carrier protein synthase, 3-ketoacyl-acp synthase, beta-ketoacyl-acp synthase i, beta-ketoacyl-acyl carrier protein synthase i, fatty acid condensing enzyme,
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beta-ketoacyl [ACP] synthase
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beta-ketoacyl-ACP synthase
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3-ketoacyl-acyl carrier protein synthase
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3-oxoacyl-[acyl-carrier-protein] synthase
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acyl-malonyl(acyl-carrier-protein)-condensing enzyme
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beta-ketoacyl acyl carrier protein synthase
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beta-ketoacyl synthetase
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beta-ketoacyl-ACP synthetase
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beta-ketoacyl-acyl carrier protein synthetase
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beta-ketoacyl-[acyl carrier protein] synthase
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beta-ketoacylsynthase
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condensing enzyme
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fatty acid condensing enzyme
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synthase, 3-oxoacyl-[acyl-carrier-protein]
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an acyl-[acyl-carrier protein] + a malonyl-[acyl-carrier protein] = a 3-oxoacyl-[acyl-carrier protein] + CO2 + an [acyl-carrier protein]
structure-activity analysis, reaction mechanism
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Acyl group transfer
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-, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -, -
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acyl-[acyl-carrier protein]:malonyl-[acyl-carrier protein] C-acyltransferase (decarboxylating)
This enzyme is responsible for the chain-elongation step of dissociated (type II) fatty-acid biosynthesis, i.e. the addition of two C atoms to the fatty-acid chain. Escherichia coli mutants that lack this enzyme are deficient in unsaturated fatty acids. The enzyme can use fatty acyl thioesters of ACP (C2 to C16) as substrates, as well as fatty acyl thioesters of Co-A (C4 to C16) [4]. The substrate specificity is very similar to that of EC 2.3.1.179, beta-ketoacyl-ACP synthase II, with the exception that the latter enzyme is far more active with palmitoleoyl-ACP (C16Delta9) as substrate, allowing the organism to regulate its fatty-acid composition with changes in temperature [4,5].
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acetyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxobutanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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butanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxohexanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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decanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
dodecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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dodecanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxotetradecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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hexanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxooctanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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myristoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxohexadecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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octanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxodecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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palmitoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
3-oxooctadecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
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additional information
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additional information
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KAS catalyzes the C2 fatty acid elongation reaction using a Cys-His-His catalytic triad
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additional information
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KAS catalyzes the C2 fatty acid elongation reaction using a Cys-His-His catalytic triad
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additional information
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important role in generation of the lipoic acid precursor octanoyl-acyl-carrier protein
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additional information
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preference for acyl-[acyl-carrier protein] in decreasing order: C12, C10, C6, C8, C4, C2, C14, C16
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additional information
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important role in generation of the lipoic acid precursor octanoyl-acyl-carrier protein
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cerulenin
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50% inhibition at 0.2 mM
additional information
inhibitor binding structure determination
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additional information
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inhibitor binding structure determination
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beta-ketoacyl-[acyl-carrier-protein] synthase i deficiency
OsKASI, a ?-ketoacyl-[acyl carrier protein] synthase I, is involved in root development in rice (Oryza sativa L.).
Breast Neoplasms
Triclosan inhibits enoyl-reductase of type I fatty acid synthase in vitro and is cytotoxic to MCF-7 and SKBr-3 breast cancer cells.
Myocardial Infarction
Condensing enzyme levels in the serum after experimental myocardial infarction.
Neoplasms
Application of a flexible synthesis of (5R)-thiolactomycin to develop new inhibitors of type I fatty acid synthase.
Tuberculosis
A novel interaction linking the FAS-II and phthiocerol dimycocerosate (PDIM) biosynthetic pathways.
Tuberculosis
Acetylene-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme.
Tuberculosis
Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme.
Tuberculosis
Identification of 2-Aminothiazole-4-Carboxylate Derivatives Active against Mycobacterium tuberculosis H(37)R(v) and the beta-Ketoacyl-ACP Synthase mtFabH.
Tuberculosis
In Silico Drug Design of Thiolactomycin Derivatives Against Mtb-KasA Enzyme to Inhibit Multidrug Resistance of Mycobacterium tuberculosis.
Tuberculosis
Inhibition of a Mycobacterium tuberculosis beta-ketoacyl ACP synthase by isoniazid.
Tuberculosis
Mycolic acid biosynthesis and enzymic characterization of the beta-ketoacyl-ACP synthase A-condensing enzyme from Mycobacterium tuberculosis.
Tuberculosis
Purification and biochemical characterization of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthases KasA and KasB.
Tuberculosis
Structural basis for the recognition of mycolic acid precursors by KasA, a condensing enzyme and drug target from Mycobacterium tuberculosis.
Tuberculosis
X-ray crystal structure of Mycobacterium tuberculosis beta-ketoacyl acyl carrier protein synthase II (mtKasB).
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0.05
acetyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0039
butanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0018
decanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0095
dodecanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0019
hexanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0508
myristoyl-[acyl-carrier protein]
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pH 6.8, 37°C
0.0109
octanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
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91.2
butanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
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decanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
303
dodecanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
353
hexanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
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myristoyl-[acyl-carrier protein]
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pH 6.8, 37°C
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octanoyl-[acyl-carrier protein]
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pH 6.8, 37°C
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the human beta-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase
SwissProt
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low level
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most abundant
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low level
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low level
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most abundant
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low level
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beta-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase
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OXSM_HUMAN
459
0
48843
Swiss-Prot
Mitochondrion (Reliability: 2 )
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45800
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x * 45800, SDS-PAGE, recombinant protein without N-terminal targeting sequence, with His-tag
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dimer
secondary structure, a dimer with an alpha-beta-alpha-beta-alpha-thiolase fold capped by an alpha-helical region connecting the strands of the N-terminal beta-sheet, crystal structure analysis
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x * 45800, SDS-PAGE, recombinant protein without N-terminal targeting sequence, with His-tag
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proteolytic modification
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mitochondrial targeting sequence of 38 residues
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purified recombinant enzyme free or complexed with acyl-CoA, hanging drop vapour diffusion method, 0.002 ml of protein solution, containing 0.087 mg of protein with or without 4 mM hexanoyl-CoA, mixed with 0.002 ml of reservoir solution containing 24% w/v PEG 3350 and 0.2 M NH4Cl, 5-8 days at room temperature, rod-shaped single crystals, X-ray diffraction structure determination and analysis at 1.6 A resolution, structure modeling
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recombinant His-tagged enzyme from Escherichia coli strains XL-1 blue and M15
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expression of the His-tagged enzyme in Escherichia coli strains XL-1 blue and M15
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drug development
the enzyme is a target for antibacterial drugs
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Zhang, L.; Joshi, A.K.; Hofmann, J.; Schweizer, E.; Smith, S.
Cloning, expression, and characterization of the human mitochondrial beta-ketoacyl synthase. Complementation of the yeast CEM1 knock-out strain
J. Biol. Chem.
280
12422-12429
2005
Homo sapiens
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Christensen, C.E.; Kragelund, B.B.; von Wettstein-Knowles, P.; Henriksen, A.
Structure of the human beta-ketoacyl [ACP] synthase from the mitochondrial type II fatty acid synthase
Protein Sci.
16
261-272
2007
Homo sapiens (Q9NWU1), Homo sapiens
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