[32] Synthesis of radioactive (−)-carnitine from γ-aminobutyrate

作者: Shri V. Pande

DOI: 10.1016/S0076-6879(86)23034-7

关键词: DemethylationColumn chromatographyIon exchangeChromatographyMethyl groupMethyl iodideMannitolDithiothreitolAmmonium sulfateChemistry

摘要: Publisher Summary This chapter discusses the Synthesis of Radioactive (—)-carnitine from γ-aminobutyrat. γ-Aminobutyrate is methylated to γ-butyrobetaine using radioactive methyl iodide under conditions giving high yields with respect both these precursors. γ-Butyrobetaine then quantitatively converted a 50–60% ammonium sulfate fraction rat liver supernatant as source hydroxylase. The product purified by column chromatography on cation exchanger and desalted passing through ion-retardation resin. A employed obtained follows: thirty percent (w/v) homogenate adult prepared in 210 m M mannitol, 70 sucrose, 0.1 mM EDTA, 10 Tris–HCl (pH 7.4), dithiothreitol Potter–Elvehjem homogenizer centrifuged at 17,000 g for min. All operations are carried out 0–4°. assay procedure involves methylation γ-aminobutyrate γ-butyrobetaine, conversion (—)-carnitine, characterization (—)-carnitine. ability hydroxylase hydroxylate stereospecifically ensures stereochemical purity synthesized method presented chapter; conversely procedures that employ β -hydroxy intermediate group acceptor, limited acceptor employed. Methyl-labeled can also be which demethylation commercial obtain (—)dimethylamino- -hydroxybutyrate back iodide.

参考文章(11)
R. Parvin, Shri V. Pande, Microdetermination of (-)carnitine and carnitine acetyltransferase activity. Analytical Biochemistry. ,vol. 79, pp. 190- 201 ,(1977) , 10.1016/0003-2697(77)90393-1
Albert Daveluy, Rehana Parvin, Shri V. Pande, Enzymatic synthesis of radioactive (−)-carnitine from γ-butyrobetaine prepared by the methylation of γ-aminobutyric acid Analytical Biochemistry. ,vol. 119, pp. 286- 292 ,(1982) , 10.1016/0003-2697(82)90587-5
J. Kerner, L.L. Bieber, A radioisotopic-exchange method for quantitation of short-chain (acid-soluble) acylcarnitines. Analytical Biochemistry. ,vol. 134, pp. 459- 466 ,(1983) , 10.1016/0003-2697(83)90323-8
J. WILLNER, S. GINSBURG, S. DIMAURO, Active transport of carnitine into skeletal muscle. Neurology. ,vol. 28, pp. 721- 721 ,(1978) , 10.1212/WNL.28.7.721
Horst Schulz, Efraim Racker, Carnitine transport in submitochondrial particles and reconstituted proteoliposomes Biochemical and Biophysical Research Communications. ,vol. 89, pp. 134- 140 ,(1979) , 10.1016/0006-291X(79)90954-9
Oddvar Stokke, Jon Bremer, A simple method for preparation of methyl-labelled (—) carnitine Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. ,vol. 218, pp. 552- 554 ,(1970) , 10.1016/0005-2760(70)90021-4
Stephen T. Ingalls, Charles L. Hoppel, Julia S. Turkaly, Synthesis of radioactively methyl-labelled (l)-carnitine Journal of Labelled Compounds and Radiopharmaceuticals. ,vol. 19, pp. 535- 541 ,(1982) , 10.1002/JLCR.2580190408
Heinz Löster, Hermann Seim, Erich Strack, Self-decomposition of DL-/methyl-14C/carnitine to labelled β-methylcholine and acetonyltrimethylammonium Journal of Labelled Compounds and Radiopharmaceuticals. ,vol. 20, pp. 1035- 1045 ,(1983) , 10.1002/JLCR.2580200902