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Org Lett. 2008 Mar 20;10(6):1111-4. doi: 10.1021/ol7030747. Epub 2008 Feb 20.

Synthesis, pharmacology, and cell biology of sn-2-aminooxy analogues of lysophosphatidic acid.

Author information

1
Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Salt Lake City, UT 84108-1257, USA.

Abstract

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.

PMID:
18284246
PMCID:
PMC3510981
DOI:
10.1021/ol7030747
[Indexed for MEDLINE]
Free PMC Article

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