Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

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

doi:10.1021/ol0358758

Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

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

研究成果: Article › 査読

22 被引用数 (Scopus)

抄録

(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.

本文言語	English
ページ（範囲）	4685-4688
ページ数	4
ジャーナル	Organic letters
巻	5
号	24
DOI	https://doi.org/10.1021/ol0358758
出版ステータス	Published - 2003 11月 27
外部発表	はい

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol0358758

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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.",

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T1 - Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

AU - Qian, Lian

AU - Xu, Yong

AU - Arai, Hiroyuki

AU - Aoki, Junken

AU - McIntyre, Thomas M.

AU - Prestwich, Glenn D.

PY - 2003/11/27

Y1 - 2003/11/27

N2 - (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.

AB - (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.

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Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

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