Synthesis of enantiomerically pure lysophosphatidylinositols and alkylphosphoinositols.
A convenient synthesis for enantiomeric pure 1-O-(1'-O-alkyl-sn-glycero-3'-phospho)-D (or L)-myo-inositol, 1-O-(1'-O-acyl-sn-glycero-3'-phospho)-D (or L)-myo-inositol and alkylphospho-1-D (or L)-myo-inositol has been described. Starting from myo-inositol, penta-O-acetyl-myo-inositol was made in five steps. Then enantiomeric purification was done by a diastereomeric salts separation method, and the purity of each enantiomer was spectroscopically measured (19F-NMR). The phosphodiester was made via phosphoramidites. The enantiomeric products (greater than 99% optical purity) of all compounds were easily obtained in large quantities (5-10 g). Synthetic phosphatidylinositol analogues of precisely defined structure and configuration are interesting tools for studying signal transduction mechanism and cell activity modulation.
Filthuth
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E
Max-Planck-Institut für biophysikalische Chemie, Göttingen, Germany.
Eibl
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H
D008246:Lysophospholipids / Q000138:chemical synthesis*; D010716:Phosphatidylinositols / Q000138:chemical synthesis*; D010766:Phosphorylation; D013237:Stereoisomerism
D008246:Lysophospholipids; D010716:Phosphatidylinositols; C025449:lysophosphatidylinositol