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Stereochemical Properties of Lysophosphatidic Acid Receptor Activation and Metabolism

Stereochemical Properties of Lysophosphatidic Acid Receptor Activation and Metabolism

Kazuaki Yokoyama, Daniel L Baker, Tamas Virag, Karoly Liliom, Hoe Sup Byun, Gabor Tigyi, Robert Bittman

Biochim Biophys Acta. 2002 May 23;1582(1-3):295-308.

PMID: 12069841

Abstract:

Ligand recognition by G protein-coupled receptors (GPCR), as well as substrate recognition by enzymes, almost always shows a preference for a naturally occurring enantiomer over the unnatural one. Recognition of lysophosphatidic acid (LPA) by its receptors is an exception, as both the natural L (R) and unnatural D (S) stereoisomers of LPA are equally active in bioassays. In contrast to the enantiomers of LPA, analogs of N-acyl-serine phosphoric acid (NASPA) and N-acyl-ethanolamine phosphoric acid (NAEPA), which contain a serine and an ethanolamine backbone, respectively, in place of glycerol, are recognized in a stereoselective manner. This stereoselective interaction may lead to the development of receptor subtype-selective antagonists. In the present study, we review the stereochemical aspects of LPA pharmacology and describe the chemical synthesis of pure LPA enantiomers together with their ligand-binding properties toward the LPA1, LPA2, and LPA3 receptors and their metabolism by lipid phosphate phosphatase 1 (LPP1). Finally, we evaluate the concept of stereopharmacology in developing novel ligands for LPA receptors.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP24435254	NAEPA		24435-25-4	Price

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