Synthesis of 2-[6-(2,4-dinitrophenoxy)hexyl]oxiranecarboxylic acid: a selective carnitine palmitoyltransferase-1 inhibitor.
Carnitine palmitoyltransferases 1 and 2 (CPT-1 and CPT-2) catalyze the transfer of long chain fatty acids between carnitine and coenzyme A. Unlike CPT-2, CPT-1 exists in at least two isoforms with different physical and kinetic properties. Liver and skeletal muscle each contain a different isoform of CPT-1. Cardiac muscle contains both isoforms, and the minor component is identical to the isoform found in the liver. 2-[6-(2,4-Dinitrophenoxy)hexyl]oxiranecarboxylic acid (2) was reported to be a selective inhibitor for the liver isoform of CPT-1. A synthesis of 2 is described here which involves the reaction of diethyl malonate with 1-bromo-6-phenoxyhexane.
Hutchison
T L
TL
Department of Chemistry, University of Alabama at Birmingham 35294, USA.
Brouillette
W J
WJ
D000818:Animals; D002334:Carnitine O-Palmitoyltransferase / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D008099:Liver / Q000201:enzymology; D008968:Molecular Conformation; D015394:Molecular Structure; D018482:Muscle, Skeletal / Q000201:enzymology; D009206:Myocardium / Q000201:enzymology
C116778:2-(6-(2,4-dinitrophenoxy)hexyl)oxirane carboxylic acid; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007527:Isoenzymes; D002334:Carnitine O-Palmitoyltransferase