Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

Lian Qian, Yong Xu, Hiroyuki Arai, Junken Aoki, Thomas M. McIntyre, Glenn D. Prestwich

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

(Matrix presented) 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 regloisomers. 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 LPA2 or LPA3 G-protein-coupted receptors, the LPA3 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.

Original languageEnglish
Pages (from-to)4685-4688
Number of pages4
JournalOrganic letters
Volume5
Issue number24
DOIs
Publication statusPublished - 2003 Nov 27
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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