ORGN 507 |
| Zdzislaw M. Szulc, Yusuf A. Hannun, and Alicja Bielawska. Department of Biochemistry and Molecular Biology, Medical University of South Carolina, 173 Ashley Avenue, Charleston, SC 29425 |
| In recent years, there have been significant efforts directed towards the development of methods for the efficient synthesis of naturally occurring phospholipids and their analogs. We have developed a novel and practical three-component phosphorylation system (TCPS) for the efficient and regioselective introduction of a phosphoryl-group into the sphingolipid system. This method utilizes trimethyl phosphite as a phosphorylation reagent, 1,2-dibromotetrachloroethane as an oxidizer, and an aqueous solution of NaOH as a base. Using N-Boc-protected D-erythro-sphingosine as a model substrate, and performing the TCPS protocol under two-phase-catalyzed conditions, the corresponding 1-O-phosphate dimethyl ester was obtained in 92% yield. The prepared ester was easily transformed to D-erythro-sphingosine 1-phosphate (SPP) using TMSCl/NaI in acetonitrile. The invented optimized process delivered high purity SPP (>95%) with 70% overall yield,when scaled-up from 1- to 50-mmol. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry |