79250-93-4Relevant academic research and scientific papers
Synthesis of a Carba-analog of S-Palmitoyl-Coenzyme A, Heptadecan-2-onyldethio-CoA, and of S-Heptadecyl-CoA; Effective Inhibitors of Citrate Synthase and Carnitine Palmitoyltransferase
Ciardelli, Thomas,Stewart, Charles J.,Seelinger, Annemarie,Wieland, Theodor
, p. 828 - 841 (2007/10/02)
The syntheses of long chain alkyl-coenzyme A derivatives 1 and 2 are reported.Heptadecan-2-onyldethio-CoA (1) a carba analog of S-palmitoyl-CoA is obtained along with its 2'-phosphate isomer 11 by the condensation of adenosine 2',3'-cyclic phosphate-5'-phosphoromorpholidate (10) with the in situ generated palmitoyldethio-carbapantetheine phosphate (8a).The cyclic phosphodiester produced upon hydrolysis yields a mixture of 3'-phosphate 1 and 2'-phosphate 11.S-Heptadecyl-CoA (2) is obtained from the alkylation of CoA with heptadecyl iodide.Both the isomeric mixture (1 + 11) and compound 2 exhibit characteristics of non-competitive inhibition with citrate synthase (K1 = 6.0-7.5 E-6 mol/l and 1.0-1.5 E-6 mol/l, respectively) and characteristics of competitive inhibition with carnitine palmitoyltransferase (K1 = 1.35 E-6 mol/l and 3.34 E-6 mol/l, respectively.
