Patent ID: 6737536
Filing Date: 2004-05-18
Classification: C07F

Abstract:
A process for synthesizing a substantially single diastereomeric form of an inositolphospholipid, wherein said inositolphospholipid has the target phosphatidyl-myo-inositol structure:1D-1-(1-fattyacyl1-2-fattyacyl2-sn-glycero-3-phospho)-myo-inositol; 1D-1-(3-fattyacyl1-2-fattyacyl2-sn-glycero-1-phospho)-myo-inositol; 1L-1-(1-fattyacyl1-2-fattyacyl2-sn-glycero-1-phospho)-myo-inositol; 1L-1-(3-fattyacyl1-2-fattyacyl2-sn-glycero-1-phospho)-myo-inositol; wherein fattyacyl1 and fattyacyl2 are identical or non-identical; said process comprising the steps of: (a) obtaining a lipid synthon, wherein said lipid synthon is a substantially pure enantiomeric form of 1-fattyacyl1-2-fattyacyl2-sn-glycero-3-phosphoric acid or 3-fattyacyl1-2-fattyacyl2-sn-glycero-1-phosphoric acid; (b) obtaining a myo-inositol synthon, wherein said myo-inositol synthon is a substantially pure enantiomeric form of a selectively partially O-protected 1D-1-myo-inositol, wherein at least the 1-equatorial hydroxyl is free, the 3-hydroxyl and at least three other hydroxyls carry temporary O-protecting groups; (c) reacting said lipid synthon with said myo-inositol synthon in the presence of a phosphoric group activating reagent system, thereby linking the two synthons by a phosphodiester bond and creating an O-protected derivative of the target phosphatidyl-myo-inositol as an intermediate; and (d) subjecting said O-protected intermediate to a deprotection process to completely remove the protecting groups, thereby forming the target phosphatidyl-myo-inositol diastereomer.