Abstract
| - Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) is an important phospholipid mediatorproduced by activated platelets and by ovarian cancer cells.Efforts to understand LPA signaling through G-protein-coupled receptors are hampered by the facile acyl migrationthat results in equilibration to a mixture of the 1- or 2-acylspecies under physiological conditions. We describe a newand efficient route to enantiomerically homogeneous lysophospholipid analogues from d-mannitol 1,2:5,6-bis-acetonide to give two 1,1-difluorodeoxy analogues of (2R)-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the labile sn-2 LPA species. The 19FNMR of diastereotopic fluorines of the difluoromethyl groupshows an unexpected solvent dependence.
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