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

Szulc, Z. M.; Obeid, L. M.; Hannun, Y. A.; Bielawska, A.

Artykuł - szczegóły

Tytuł artykułu

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

Autorzy

Szulc Z. M. , Obeid L. M. , Hannun Y. A. , Bielawska A.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

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

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, szulcz@musc.edu

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ5-0017-0023