An efficient enantioselective synthesis of sn-2-aminooxy (AO) analogues of lysophosphatidic acid (LPA) that possess palmitoyl and oleoyl acyl chains is presented. Both sn-2-AO LPA analogues are agonists for the LPA1, LPA2, and LPA4 G-protein-coupled receptors, but antagonists for the LPA3 receptor and inhibitors of autotaxin (ATX). Moreover, both analogues stimulate migration of intestinal epithelial cells in a scratch wound assay.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3510981 | PMC |
| http://dx.doi.org/10.1021/ol7030747 | DOI Listing |
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Synthesis, pharmacology, and cell biology of sn-2-aminooxy analogues of lysophosphatidic acid.
Org Lett
March 2008
Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Salt Lake City, UT 84108-1257, USA.
An efficient enantioselective synthesis of sn-2-aminooxy (AO) analogues of lysophosphatidic acid (LPA) that possess palmitoyl and oleoyl acyl chains is presented. Both sn-2-AO LPA analogues are agonists for the LPA1, LPA2, and LPA4 G-protein-coupled receptors, but antagonists for the LPA3 receptor and inhibitors of autotaxin (ATX). Moreover, both analogues stimulate migration of intestinal epithelial cells in a scratch wound assay.
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