Highly Efficient and Regioselective Phosphorylation of Sphingolipids by Phase-Trans fer Catalysis

• Autorzy: Szulc Z. M. , Obeid L. M. , Hannun Y. A. , Bielawska A.
• Języki publikacji: EN

Abstrakty

EN

Phosphorylation of D-erythro-sphingosine and its N-BOC or N-palmitoyl derivatives with trimethyl phosphite was carried out in 72–92% yield at room temperature for 20 min in a biphasic system comprised of dichloromethane/aqueous solutions of NaOH or K2CO3 using 1,2-dibromotetrachloroethane as a source of halogen and cetylpyridinium bromide as a phase-transfer catalyst. These are the first reported examples of a highly selective O- and N-phosphorylation of sphingolipids by the phase-transfer catalysis. Our studies show that the developed phosphorylation protocol works as a modular process, in which the synthetic out come is controlled by a type of the used base, catalyst and solvent system.

Słowa kluczowe

EN

phosphorylation; trimethyl phosp; 1,2-dibromotetrachloroethane; phase-transfer catalysis; sphingosine; ceramide; sphingosine 1-phosphate; ceramide 1-phosphate

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 11
• Strony: 1899--1909
• Opis fizyczny: Bibliogr. 56 poz., rys.

Twórcy

autor

Szulc Z. M.

autor

Obeid L. M.

autor

Hannun Y. A.

autor

Bielawska A.

• Departments of Biochemistry and Molecular Biology, Medical University of South Carolina, Charleston, SC 29425, USA,

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