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Volumn 244, Issue 2, 1997, Pages 434-440

Stereochemistry of peroxisomal and mitochondrial β-oxidation of α-methylacyl-CoAs

Author keywords

Acyl CoA oxidase; Branched chain fatty acid; Peroxisome; Racemase; Oxidation

Indexed keywords

ACYL COENZYME A;

EID: 0031053480     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00434.x     Document Type: Article
Times cited : (33)

References (46)
  • 1
    • 51249187265 scopus 로고
    • The occurrence of diastereomers of phytanic and pristanic acids and their determination by gas-liquid chromatography
    • Ackman, R. G. & Hansen, R. P. (1967) The occurrence of diastereomers of phytanic and pristanic acids and their determination by gas-liquid chromatography, Lipids 2, 357-362.
    • (1967) Lipids , vol.2 , pp. 357-362
    • Ackman, R.G.1    Hansen, R.P.2
  • 4
    • 0018581367 scopus 로고
    • Cleavage of the taurine conjugate of 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid by rat fecal bacteria
    • Batta, A. K., Salen, G., Cheng, F. W. & Shefer, S. (1979) Cleavage of the taurine conjugate of 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid by rat fecal bacteria, J. Biol. Chem. 254, 11907-11909.
    • (1979) J. Biol. Chem. , vol.254 , pp. 11907-11909
    • Batta, A.K.1    Salen, G.2    Cheng, F.W.3    Shefer, S.4
  • 5
    • 0020665789 scopus 로고
    • Configuration at C-25 in 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid isolated from human bile
    • Batta, A. K., Salen, G., Shefer, S., Dayal, B. & Tint, G. S. (1983) Configuration at C-25 in 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid isolated from human bile, J. Lipid Res. 24, 94-96.
    • (1983) J. Lipid Res. , vol.24 , pp. 94-96
    • Batta, A.K.1    Salen, G.2    Shefer, S.3    Dayal, B.4    Tint, G.S.5
  • 6
    • 0000747184 scopus 로고
    • Stereochemistry of the oxidation at the α carbon of butyryl-CoA and of the enzymic hydrogen exchange
    • Biellmann, J. F. & Hirth, C. G. (1970) Stereochemistry of the oxidation at the α carbon of butyryl-CoA and of the enzymic hydrogen exchange, FEBS Lett. 9, 335-336.
    • (1970) FEBS Lett. , vol.9 , pp. 335-336
    • Biellmann, J.F.1    Hirth, C.G.2
  • 7
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 8
    • 0014963548 scopus 로고
    • Zur Stereochemie der enzymatischen Dehydrierung von Butyryl-CoA
    • Bücklers, L., Umani-Ronchi, A., Rétey, J. & Arigoni, D. (1970) Zur Stereochemie der enzymatischen Dehydrierung von Butyryl-CoA, Experientia 26, 931-933.
    • (1970) Experientia , vol.26 , pp. 931-933
    • Bücklers, L.1    Umani-Ronchi, A.2    Rétey, J.3    Arigoni, D.4
  • 9
    • 0023835819 scopus 로고
    • The metabolic chiral inversion and dispositional enantioselectivity of the 2-aryl-propionic acids and their biological consequences
    • Caldwell, J., Hutt, A. J. & Fournel-Gigleux, S. (1988) The metabolic chiral inversion and dispositional enantioselectivity of the 2-aryl-propionic acids and their biological consequences, Biochem. Pharmacol 37, 105-114.
    • (1988) Biochem. Pharmacol , vol.37 , pp. 105-114
    • Caldwell, J.1    Hutt, A.J.2    Fournel-Gigleux, S.3
  • 10
    • 0000771954 scopus 로고
    • A simple one-pot sythesis of nitriles from alcohols
    • Camps, F., Gasol, V. & Guerrero, A. (1988) A simple one-pot sythesis of nitriles from alcohols, Synth. Commun. 18, 445-452.
    • (1988) Synth. Commun. , vol.18 , pp. 445-452
    • Camps, F.1    Gasol, V.2    Guerrero, A.3
  • 13
    • 0027217062 scopus 로고
    • Accumulation of phytanic acid α-oxidation intermediates in Zellweger fibroblasts
    • Fingerhut, R., Schmitz, W. & Conzelmann, E. (1993) Accumulation of phytanic acid α-oxidation intermediates in Zellweger fibroblasts, J. Inherited Metab. Dis. 16, 591-594.
    • (1993) J. Inherited Metab. Dis. , vol.16 , pp. 591-594
    • Fingerhut, R.1    Schmitz, W.2    Conzelmann, E.3
  • 14
    • 0018980537 scopus 로고
    • Biosynthesis of cholic acid in rat liver: Formation of cholic acid from 3α,7α,12α-trihydroxy- and 3α,7α,12α,24-tetrahydroxy-5β-cholestanoic acids
    • Gustafsson, J. (1980) Biosynthesis of cholic acid in rat liver: Formation of cholic acid from 3α,7α,12α-trihydroxy- and 3α,7α,12α,24-tetrahydroxy-5β-cholestanoic acids, Lipids 15, 113-121.
    • (1980) Lipids , vol.15 , pp. 113-121
    • Gustafsson, J.1
  • 15
    • 0013771565 scopus 로고
    • The isolation and identification of 2,6,10,14-tetramethylpentadecanoic acid from butterfat
    • Hansen, R. P. & Morrison, J. D. (1964) The isolation and identification of 2,6,10,14-tetramethylpentadecanoic acid from butterfat, Biochem. J. 93, 225-229.
    • (1964) Biochem. J. , vol.93 , pp. 225-229
    • Hansen, R.P.1    Morrison, J.D.2
  • 16
    • 0014378897 scopus 로고
    • Chemistry and metabolism of bile alcohols and higher bile acids
    • Hoshita, T. & Kazuno, T. (1968) Chemistry and metabolism of bile alcohols and higher bile acids, Adv. Lipid Res. 6, 207-254.
    • (1968) Adv. Lipid Res. , vol.6 , pp. 207-254
    • Hoshita, T.1    Kazuno, T.2
  • 17
    • 4244105784 scopus 로고
    • Titanyl sulfate method for the detection of catalase in blood, serum and urine
    • Hübl, P. & Bretschneider, R. (1964) Titanyl sulfate method for the detection of catalase in blood, serum and urine, Hoppe-Seyler's Z. Physiol. Chem. 335, 146-155.
    • (1964) Hoppe-Seyler's Z. Physiol. Chem. , vol.335 , pp. 146-155
    • Hübl, P.1    Bretschneider, R.2
  • 18
    • 0021099782 scopus 로고
    • Purification and characterization of 2-methyl-branched-chain acyl coenzyme A dehydrogenase, an enzyme involved in the isoleucine and valine metabolism, from rat liver mitochondria
    • Ikeda, Y. & Tanaka, K. (1983) Purification and characterization of 2-methyl-branched-chain acyl coenzyme A dehydrogenase, an enzyme involved in the isoleucine and valine metabolism, from rat liver mitochondria, J. Biol. Chem. 258, 9477-9487.
    • (1983) J. Biol. Chem. , vol.258 , pp. 9477-9487
    • Ikeda, Y.1    Tanaka, K.2
  • 19
    • 0029151907 scopus 로고
    • Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisomes
    • Ikegawa, S., Goto, T., Watanabe, H. & Goto, J. (1995) Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisomes, Biol. Pharm. Bull. 18, 1027-1029.
    • (1995) Biol. Pharm. Bull. , vol.18 , pp. 1027-1029
    • Ikegawa, S.1    Goto, T.2    Watanabe, H.3    Goto, J.4
  • 20
    • 0025257450 scopus 로고
    • The enzymatic basis for the metabolism and inhibitory effects of valproic acid: Dehydrogenation of valproyl-CoA by 2-methyl-branched-chain acyl-CoA dehydrogenase
    • Ito, M., Ikeda, Y., Arnez, J. G., Finocchiaro, G. & Tanaka, K. (1990) The enzymatic basis for the metabolism and inhibitory effects of valproic acid: dehydrogenation of valproyl-CoA by 2-methyl-branched-chain acyl-CoA dehydrogenase, Biochim. Biophys. Acta 1034, 213-218.
    • (1990) Biochim. Biophys. Acta , vol.1034 , pp. 213-218
    • Ito, M.1    Ikeda, Y.2    Arnez, J.G.3    Finocchiaro, G.4    Tanaka, K.5
  • 21
    • 0027426259 scopus 로고
    • Molecular cloning of the cDNAs for the subunits of rat mitochondrial β-oxidation multienzyme complex. Structural and functional relationships to other mitochondrial and peroxisomal β-oxidation enzymes
    • Kamijo, T., Aoyama, T., Miyazaki, J. & Hashimoto, T. (1993) Molecular cloning of the cDNAs for the subunits of rat mitochondrial β-oxidation multienzyme complex. Structural and functional relationships to other mitochondrial and peroxisomal β-oxidation enzymes, J. Biol. Chem. 268, 26452-26460.
    • (1993) J. Biol. Chem. , vol.268 , pp. 26452-26460
    • Kamijo, T.1    Aoyama, T.2    Miyazaki, J.3    Hashimoto, T.4
  • 22
    • 0024507290 scopus 로고
    • 27-steroid side chain cleavage in peroxisome deficiency (Zellweger syndrome)
    • 27-steroid side chain cleavage in peroxisome deficiency (Zellweger syndrome), Scand. J. Clin. Lab. Invest. 49, 1-10.
    • (1989) Scand. J. Clin. Lab. Invest. , vol.49 , pp. 1-10
    • Kase, B.F.1
  • 24
    • 0023694507 scopus 로고
    • Enantiospecific formation of fenoprofen coenzyme A thioester
    • Knights, K. M., Drew, R. & Meffin, P. J. (1988) Enantiospecific formation of fenoprofen coenzyme A thioester, Biochem. Pharmacol. 37, 3539-3542.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 3539-3542
    • Knights, K.M.1    Drew, R.2    Meffin, P.J.3
  • 25
    • 0024787109 scopus 로고
    • Chiral inversion of 2-aryl-propionic acid non-steroidal anti-inflammatory drugs. 1. in vitro studies of ibuprofen and flurbiprofen
    • Knihinicki, R. D., Williams, K. M. & Day, R. O. (1989) Chiral inversion of 2-aryl-propionic acid non-steroidal anti-inflammatory drugs. 1. In vitro studies of ibuprofen and flurbiprofen, Biochem. Pharmacol. 38, 4389-4395.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 4389-4395
    • Knihinicki, R.D.1    Williams, K.M.2    Day, R.O.3
  • 27
    • 0019333103 scopus 로고
    • Acyl-CoA synthetase in rat liver peroxisomes. Computer-assisted analysis of cell fractionation experiments
    • Krisans, S. K., Mortensen, R. M. & Lazarow, P. B. (1980) Acyl-CoA synthetase in rat liver peroxisomes. Computer-assisted analysis of cell fractionation experiments, J. Biol. Chem. 255, 9599-9607.
    • (1980) J. Biol. Chem. , vol.255 , pp. 9599-9607
    • Krisans, S.K.1    Mortensen, R.M.2    Lazarow, P.B.3
  • 28
    • 0021685190 scopus 로고
    • Liquid chromatographic determination and plasma concentration profile of optical isomers of ibuprofen in humans
    • Lee, E. D. J., Williams, K. M. Graham, G. G., Day, R. O. & Champion, G. D. (1984) Liquid chromatographic determination and plasma concentration profile of optical isomers of ibuprofen in humans, J. Pharmacol. Sci. 73, 1542-1544.
    • (1984) J. Pharmacol. Sci. , vol.73 , pp. 1542-1544
    • Lee, E.D.J.1    Williams, K.M.2    Graham, G.G.3    Day, R.O.4    Champion, G.D.5
  • 29
    • 0025374115 scopus 로고
    • An acyl-coenzyme A dehydrogenase assay utilizing the ferricenium ion
    • Lehmann, T. C., Hale, D. E., Bhala, A. & Thorpe, C. (1990) An acyl-coenzyme A dehydrogenase assay utilizing the ferricenium ion, Anal. Biochem. 186, 280-284.
    • (1990) Anal. Biochem. , vol.186 , pp. 280-284
    • Lehmann, T.C.1    Hale, D.E.2    Bhala, A.3    Thorpe, C.4
  • 30
    • 0020483106 scopus 로고
    • Evidence that peroxisomal acyl-CoA synthetase is located at the cytoplasmic side of the peroxisomal membrane
    • Mannaerts, G. P., Van Veldhoven, P., van Broekhoven, A., Vandenbrock, G. & Debeer, L. J. (1982) Evidence that peroxisomal acyl-CoA synthetase is located at the cytoplasmic side of the peroxisomal membrane, Biochem. J. 204, 17-23.
    • (1982) Biochem. J. , vol.204 , pp. 17-23
    • Mannaerts, G.P.1    Van Veldhoven, P.2    Van Broekhoven, A.3    Vandenbrock, G.4    Debeer, L.J.5
  • 31
    • 0022207621 scopus 로고
    • Hydrophilic macromolecular ferricenium salts - Part I: Preparative and spectroscopic features of selected mononuclear ferricenium compounds
    • (Sheats, J. E., Carraher, C. E. Jr & Pittman, C. V. Jr, eds), Plenum Press, New York
    • Neuse, E. W. (1985) Hydrophilic macromolecular ferricenium salts - part I: Preparative and spectroscopic features of selected mononuclear ferricenium compounds, in Metal-containing polymer systems (Sheats, J. E., Carraher, C. E. Jr & Pittman, C. V. Jr, eds) pp. 99-136, Plenum Press, New York.
    • (1985) Metal-containing Polymer Systems , pp. 99-136
    • Neuse, E.W.1
  • 32
    • 0021713540 scopus 로고
    • Infantile Refsum's disease (phytanic acid storage disease): A variant of Zellweger's syndrome?
    • Poulos, A., Sharp, P. & Whiting, M. (1984) Infantile Refsum's disease (phytanic acid storage disease): a variant of Zellweger's syndrome? Clin. Genet. 25, 579-586.
    • (1984) Clin. Genet. , vol.25 , pp. 579-586
    • Poulos, A.1    Sharp, P.2    Whiting, M.3
  • 33
    • 0023903643 scopus 로고
    • Accumulation of pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) in the plasma of patients with generalized peroxisomal dysfunction
    • Poulos, A., Sharp, P., Fellenberg, A. J. & Johnson, D. W. (1988) Accumulation of pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) in the plasma of patients with generalized peroxisomal dysfunction, Eur. J. Pediatr. 147, 143-147.
    • (1988) Eur. J. Pediatr. , vol.147 , pp. 143-147
    • Poulos, A.1    Sharp, P.2    Fellenberg, A.J.3    Johnson, D.W.4
  • 34
    • 0028176487 scopus 로고
    • Purification and properties of an α-methylacyl-CoA racemase from rat liver
    • Schmitz, W., Fingerhut, R. & Conzelmann, E. (1994) Purification and properties of an α-methylacyl-CoA racemase from rat liver, Eur. J. Biochem. 222, 313-323.
    • (1994) Eur. J. Biochem. , vol.222 , pp. 313-323
    • Schmitz, W.1    Fingerhut, R.2    Conzelmann, E.3
  • 35
    • 0028982895 scopus 로고
    • Purification and characterization of an α-methylacyl-CoA racemase from human liver
    • Schmitz, W., Albers, C., Fingerhut, R. & Conzelmann, E. (1995) Purification and characterization of an α-methylacyl-CoA racemase from human liver, Eur J. Biochem. 231, 815-822.
    • (1995) Eur J. Biochem. , vol.231 , pp. 815-822
    • Schmitz, W.1    Albers, C.2    Fingerhut, R.3    Conzelmann, E.4
  • 36
    • 0018132389 scopus 로고
    • Biosynthesis of chenodeoxycholic acid in man. Stereospecific side-chain hydroxylation of 5β-cholestane-3α,7α-diol
    • Shefer, S., Cheng, F. W., Batta, A. K., Dayal, B., Tint, G. S. & Salen, G. (1978) Biosynthesis of chenodeoxycholic acid in man. Stereospecific side-chain hydroxylation of 5β-cholestane-3α,7α-diol, J. Clin. Invest. 62, 539-545.
    • (1978) J. Clin. Invest. , vol.62 , pp. 539-545
    • Shefer, S.1    Cheng, F.W.2    Batta, A.K.3    Dayal, B.4    Tint, G.S.5    Salen, G.6
  • 37
    • 0027468764 scopus 로고
    • Purification and characterization of novel '2-arylpropionyl-CoA epimerases' from rat liver cytosol and mitochondria
    • Shieh, W.-R. & Chen, C.-S. (1993) Purification and characterization of novel '2-arylpropionyl-CoA epimerases' from rat liver cytosol and mitochondria, J. Biol. Chem. 268, 3487-3493.
    • (1993) J. Biol. Chem. , vol.268 , pp. 3487-3493
    • Shieh, W.-R.1    Chen, C.-S.2
  • 38
    • 0001293272 scopus 로고
    • Refsum disease
    • (Scriver, C. R., Beaudet, A. L., Sly, W. S. & Valle, D., eds), McGraw-Hill, New York
    • Steinberg, D. (1995) Refsum disease, in The metabolic basis of inherited disease, 7th edn (Scriver, C. R., Beaudet, A. L., Sly, W. S. & Valle, D., eds) pp. 2351-2369, McGraw-Hill, New York.
    • (1995) The Metabolic Basis of Inherited Disease, 7th Edn , pp. 2351-2369
    • Steinberg, D.1
  • 40
    • 0026348109 scopus 로고
    • Mitochondrial and peroxisomal β-oxidation of the branched chain fatly acid 2-methylpalmitate in rat liver
    • Vanhove, G., Van Veldhoven, P. P., Vanhoutte, F., Parmentier, G., Eyssen, H. J. & Mannaerts, G. P. (1991) Mitochondrial and peroxisomal β-oxidation of the branched chain fatly acid 2-methylpalmitate in rat liver, J. Biol. Chem. 266, 24670-24675.
    • (1991) J. Biol. Chem. , vol.266 , pp. 24670-24675
    • Vanhove, G.1    Van Veldhoven, P.P.2    Vanhoutte, F.3    Parmentier, G.4    Eyssen, H.J.5    Mannaerts, G.P.6
  • 41
    • 0027159784 scopus 로고
    • The CoA esters of 2-methyl-branched chain fatty acids and of the bile acid intermediates di- and trihydroxycoprostanoic acids are oxidized by one single peroxisomal branched-chain acyl-CoA oxidase in human liver and kidney
    • Vanhove, G., Van Veldhoven, P. P., Fransen, M., Denis, S., Eyssen, H. J., Wanders, R. J. A. & Mannaerts, G. P. (1993) The CoA esters of 2-methyl-branched chain fatty acids and of the bile acid intermediates di- and trihydroxycoprostanoic acids are oxidized by one single peroxisomal branched-chain acyl-CoA oxidase in human liver and kidney, J. Biol. Chem. 268, 10335-10344.
    • (1993) J. Biol. Chem. , vol.268 , pp. 10335-10344
    • Vanhove, G.1    Van Veldhoven, P.P.2    Fransen, M.3    Denis, S.4    Eyssen, H.J.5    Wanders, R.J.A.6    Mannaerts, G.P.7
  • 43
    • 0026668028 scopus 로고
    • Substrate specificities of rat liver peroxisomal acyl-CoA oxidases: Palmitoyl-CoA oxidase (inducible acyl-CoA oxidase), pristanoyl-CoA oxidase (non-inducible acyl-CoA oxidase), and trihydroxycoprostanoyl-CoA oxidase
    • Van Veldhoven, P. P., Vanhove, G., Asselberghs, S., Eyssen, H. J. & Mannaerts, G. P. (1992) Substrate specificities of rat liver peroxisomal acyl-CoA oxidases: Palmitoyl-CoA oxidase (inducible acyl-CoA oxidase), pristanoyl-CoA oxidase (non-inducible acyl-CoA oxidase), and trihydroxycoprostanoyl-CoA oxidase, J. Biol. Chem. 267, 20065-20074.
    • (1992) J. Biol. Chem. , vol.267 , pp. 20065-20074
    • Van Veldhoven, P.P.1    Vanhove, G.2    Asselberghs, S.3    Eyssen, H.J.4    Mannaerts, G.P.5
  • 44
    • 0029898658 scopus 로고    scopus 로고
    • Peroxisomal β-oxidation of 2-methyl-branched acyl-CoA esters: Stereospecific recognition of the 2S-methyl compounds by trihydroxycoprostanoyl-CoA oxidase and pristanoyl-CoA oxidase
    • Van Veldhoven, P. P., Croes, K., Asselberghs, S., Herdewijn, P. & Mannaerts, G. P. (1996) Peroxisomal β-oxidation of 2-methyl-branched acyl-CoA esters: stereospecific recognition of the 2S-methyl compounds by trihydroxycoprostanoyl-CoA oxidase and pristanoyl-CoA oxidase, FEBS Lett. 388, 80-84.
    • (1996) FEBS Lett. , vol.388 , pp. 80-84
    • Van Veldhoven, P.P.1    Croes, K.2    Asselberghs, S.3    Herdewijn, P.4    Mannaerts, G.P.5


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