Phosphatidylserine is a cell membrane component recognized as a player in extracellular signaling of apoptosis and blood coagulation. The goal of our research is to model and characterize the geometry of this signaling membrane component in vitro with Phosphatidylserine Lipid Analogues (PLAs). Multi step synthesis of PLAs has been performed successfully, beginning with an acyl chloride activated carbobenzyloxy-L-serine-benzyl ester H-phosphonate monoester (CBZ-L-Ser-PH) (1  ) that is coupled with with a cyclohexanediol. The disubstituted H-phosphonate diester PLA precursors (2 ) have proven problematic during purification due to their tendency to degrade in the presence of nucleophilic species. The H-phosphonate diester instability has prompted investigation into new synthetic schemes and purification methods to mitigate the problem.

Synthesis of a cyclohexylbisphosphoserine as a potential phosphatidylserine analog

247th National Meeting (2014)

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