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EC Tree
IUBMB Comments alpha-methyl-branched acyl-CoA derivatives with chain lengths of more than C10 are substrates. Also active towards some aromatic compounds (e.g. ibuprofen) and bile acid intermediates, such as trihydroxycoprostanoyl-CoA. Not active towards free acids
The taxonomic range for the selected organisms is: Rattus norvegicus The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
amacr, p504s, alpha-methylacyl-coa racemase, alpha-methylacyl-coenzyme a racemase, alpha-methylacyl coenzyme a racemase, alpha-methylacyl coa racemase, amacr/p504s, 2-methylacyl-coa racemase, alpha-methyl coa racemase, 2-arylpropionyl-coa epimerase,
more
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2-arylpropionyl-CoA epimerase
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2-methylacyl-CoA racemase
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alpha-Methylacyl CoA racemase
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alpha-methylacyl-CoA racemase
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GenBank U89905-derived protein GI2145184
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GenBank U89906-derived protein GI 2145186
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Racemase, alpha-methylacyl coenzyme A
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Racemase, alpha-methylacyl coenzyme A (Mus musculus clone 3)
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Racemase, alpha-methylacyl coenzyme A (Rattus norvegicus clone 11)
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2-Methylacyl-CoA 2-epimerase
alpha-methyl-branched acyl-CoA derivatives with chain lengths of more than C10 are substrates. Also active towards some aromatic compounds (e.g. ibuprofen) and bile acid intermediates, such as trihydroxycoprostanoyl-CoA. Not active towards free acids
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197731-71-8
racemase, alpha-methylacyl coenzyme A (Mus musculus clone 3) /genBank U89906-derived protein GI 2145186
197731-72-9
racemase, alpha-methylacyl coenzyme A (Rattus norvegicus clone 11) /genBank U89905-derived protein GI2145184
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(25S)-trihydroxycoprostanoyl-CoA
(25R)-trihydroxycoprostanoyl-CoA
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?
(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
(2S)-pristanoyl-CoA
(2R)-pristanoyl-CoA
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?
(S)-2-Methylmyristoyl-CoA
(R)-2-Methylmyristoyl-CoA
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r
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?
(S)-ibuprofenoyl-CoA
(R)-ibuprofenoyl-CoA
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?
(S)-Pristanoyl-CoA
(R)-Pristanoyl-CoA
(S)-Trihydroxycoprostanoyl-CoA
(R)-Trihydroxycoprostanoyl-CoA
3alpha,7alpha,12alpha-trihydroxycholestanoyl-CoA
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pristanoyl-CoA
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additional information
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(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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?
(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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r
(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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natural substrates are branched chain alpha-methylacyl coenzyme A esters
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(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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the enzyme catalyses the chiral inversion of (2R)- and (2S)-2-methylacyl-CoA through a 1,1-proton transfer mechanism
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r
(S)-Pristanoyl-CoA
(R)-Pristanoyl-CoA
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(S)-Pristanoyl-CoA
(R)-Pristanoyl-CoA
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r
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(S)-Trihydroxycoprostanoyl-CoA
(R)-Trihydroxycoprostanoyl-CoA
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(S)-Trihydroxycoprostanoyl-CoA
(R)-Trihydroxycoprostanoyl-CoA
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r
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additional information
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additional information
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no activity with 3-methyl-branched or linear-chain acyl-CoAs
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additional information
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enzyme is involved in the alternative pathway of cholesterol side-chain oxidation. The alternative pathway consists of alpha-methylacyl-CoA racemase, and peroxisomal multifunctional enzyme type 1 (peroxisomal multifunctional 2-enoyl-CoA hydratase/(S)-3-hydroxyacyl-CoA dehydrogenase)
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additional information
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the enzyme exhibits broad substrate specificity
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(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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r
(2S)-2-methylacyl-CoA
(2R)-2-methylacyl-CoA
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natural substrates are branched chain alpha-methylacyl coenzyme A esters
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(11E)-12-iodo-2-methylidenedodec-11-enoyl-CoA
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(24S,25R)-(3R,7R,12R)-trihydroxy-24-fluoro-5beta-cholestan-26-oyl-CoA
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competitive inhibition
(2R,3S)-3-fluoro-2-methylhexadecanoyl-CoA
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competitive inhibition
(2S,3R)-3-fluoro-2-methylhexadecanoyl-CoA
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competitive inhibition
(R)-ibuprofenoyl-CoA
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competitive inhibition
(S)-ibuprofenoyl-CoA
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competitive inhibition
1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide
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13-iodo-2-methylentridec-12-enoic acid
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14-fluoro-2-methylidenetetradecanoyl-CoA
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2-(4-Isobutylphenyl)propionic acid
2-(trifluoromethyl)tetradecanoyl-CoA
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2-difluoromethylpentadecanoyl-CoA
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competitive inhibition
2-methylidenetetradecanoyl-CoA
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2-methylmyristoyl CoA
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competitive inhibition
2-methyloctanoyl CoA
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competitive inhibition
2-trifluoromethyltetradecanoic acid
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competitive inhibition
2-trifluoromethyltetradecanoyl-CoA
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competitive inhibition
5,5'-dithiobis(2-nitrobenzoate)
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inhibition is reversed by incubation of the inactivated enzyme with 10 mM dithiothreitol
alpha-trifluoromethyltetradecanoic acid
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inhibits growth of cancer cell lines PC3, CWR22 Rv1, and Du145 in a dose-dependent manner due to AMACR inhibition
beta-fluorinated branched chain alpha-methylacyl coenzyme A esters analogues
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reversible competitive inhibitors, presence of beta-fluorine on the alpha-methyl group or the acyl chain results in a significant lowering of the Ki value compared with nonfluorinated analogs, and this is attributed to a lowering of the pKa of the alpha-proton, facilitating enolization and binding, competitive
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diisopropylphosphofluoridate
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dodecylpropanedioyl-CoA
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2-(4-Isobutylphenyl)propionic acid
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2-(4-Isobutylphenyl)propionic acid
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i.e. ibuprofen, strongest of all competitive inhibitors tested
2-methylmyristoyl-CoA
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2-methylmyristoyl-CoA
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inhibits reaction with 2-pristanoyl-CoA
2-methyloctanoyl-CoA
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2-methyloctanoyl-CoA
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inhibits reaction with 2-pristanoyl-CoA
palmitoyl-CoA
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palmitoyl-CoA
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stimulates at low concentrations, inhibits above 0.1 mM
additional information
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no inhibition by iodoacetamide
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additional information
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inhibitor design and synthesis, overview
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additional information
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design of mechanism-based irreversible inhibitors, 2-methylmyrist-2-enoyl CoA is not an inhibitor, mechanism, overview
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palmitoyl-CoA
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stimulates at low concentrations, inhibits above 0.1 mM
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0.06
trihydroxycoprostanoyl-CoA
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0.0038
(24S,25R)-(3R,7R,12R)-trihydroxy-24-fluoro-5beta-cholestan-26-oyl-CoA
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pH 7.0, 37°C
0.0013
(2R,3S)-3-fluoro-2-methylhexadecanoyl-CoA
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pH 7.0, 37°C
0.0023
(2S,3R)-3-fluoro-2-methylhexadecanoyl-CoA
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pH 7.0, 37°C
0.0054
(R)-ibuprofenoyl-CoA
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pH 7.0, 37°C
0.0192
(S)-ibuprofenoyl-CoA
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pH 7.0, 37°C
0.02
2-difluoromethylpentadecanoyl-CoA
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pH 7.0, 37°C
0.137
2-methylmyristoyl CoA
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pH 7.0, 37°C
0.045
2-methyloctanoyl CoA
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pH 7.0, 37°C
0.0009
2-trifluoromethyltetradecanoyl-CoA
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pH 7.0, 37°C
additional information
additional information
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inhibition kinetics
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additional information
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development of a very sensitive and convenient radiometric assay
additional information
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development of a coupled assay based on the use of pristanoyl-CoA oxidase/peroxidase
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trihydroxycoprostanoyl-CoA
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Uniprot
brenda
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brenda
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brenda
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co-distributed exclusively with mitochondrial marker enzymes
brenda
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brenda
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bulk activity
brenda
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physiological function
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AMACR is involved in the beta-oxidation of the dietary branched-chain fatty acids and bile acid intermediate
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AMACR_RAT
382
0
41828
Swiss-Prot
other Location (Reliability: 4 )
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44900
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1 * 44900, SDS-PAGE
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monomer
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monomer
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1 * 44900, SDS-PAGE
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expression in Escherichia coli
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pharmacology
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the enzyme is partially validated as a potential therapeutic target by siRNA knockdown of the AMACR gene, overview
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Schmitz, W.; Fingerhut, R.; Conzelmann, E.
Purification and properties of an alpha-methylacyl-CoA racemase from rat liver
Eur. J. Biochem.
222
313-323
1994
Rattus norvegicus
brenda
Schmitz, W.; Albers, C.; Fingerhut, R.; Conzelmann, E.
Purification and characterization of an alpha-methylacyl-CoA racemase from human liver
Eur. J. Biochem.
231
815-822
1995
Homo sapiens, Rattus norvegicus
brenda
Schmitz, W.; Helander, H.M.; Hiltunen, J.K.; Conzelmann, E.
Molecular cloning of cDNA species for rat and mouse liver alpha-methylacyl-CoA racemase
Biochem. J.
326
883-889
1997
Mus musculus (O09174), Mus musculus, Rattus norvegicus (P70473)
brenda
Van Veldhoven, P.P.; Croes, K.; Casteels, M.; Mannaerts, G.P.
2-Methylacyl racemase: a coupled assay based on the use of pristanoyl-CoA oxidase/peroxidase and reinvestigation of its subcellular distribution in rat and human liver
Biochim. Biophys. Acta
1347
62-68
1997
Homo sapiens, Rattus norvegicus
brenda
Cuebas, D.A.; Phillips, C.; Schmitz, W.; Conzelmann, E.; Novikov, D.K.
The role of alpha-methylacyl-CoA racemase in bile acid synthesis
Biochem. J.
363
801-807
2002
Rattus norvegicus
brenda
Carnell, A.J.; Hale, I.; Denis, S.; Wanders, R.J.; Isaacs, W.B.; Wilson, B.A.; Ferdinandusse, S.
Design, synthesis, and in vitro testing of alpha-methylacyl-CoA racemase inhibitors
J. Med. Chem.
50
2700-2707
2007
Rattus norvegicus
brenda
Morgenroth, A.; Urusova, E.A.; Dinger, C.; Al-Momani, E.; Kull, T.; Glatting, G.; Frauendorf, H.; Jahn, O.; Mottaghy, F.M.; Reske, S.N.; Zlatopolskiy, B.D.
New molecular markers for prostate tumor imaging: a study on 2-methylene substituted fatty acids as new AMACR inhibitors
Chemistry
17
10144-10150
2011
Rattus norvegicus, Homo sapiens (Q9UHK6)
brenda