Synthesis of migration-resistant hydroxyethoxy analogues of lysophosphatidic acid |
| |
Authors: | Qian Lian Xu Yong Arai Hiroyuki Aoki Junken McIntyre Thomas M Prestwich Glenn D |
| |
Institution: | Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, Utah 84108-1257, USA. |
| |
Abstract: | reaction: see text] The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fail to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|