Phosphatidylserine (PS) is a negatively charged phospholipid that serves as an important component of cellular membranes. PS binds to Ca(II)-protein complexes that are involved in important biological processes such as apoptosis (programmed cell death) and blood coagulation. PS can also serve as a receiver in Targeted Drug Delivery systems because of its location on the outer cellular membrane in tumor cells. The overarching goal of this project is to synthesize cyclophosphoserine for use as a potential PS analog.  We accomplished the initial synthetic challenge of preparing and isolating the key starting material carbobenzyloxy-L-serine-benzyl ester H-phosphonate monoester (CBZ-L-Ser-PH).  1-H and 31-P NMR spectroscopy were used to confirm the product identity.  The reaction has been improved to provide the target CBZ-L-Ser-PH monoester in 96% yield.  Current work is directed toward scaling up the reaction and improving the purification.

Formation of a protected serine H-phosphonate monoester towards synthesis of cyclohexylphosphoserine as a potential phosphatidylserine analog

247th National Meeting (2014)

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