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2 Polish Journal of Chemistry

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

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

Polish Journal of Chemistry

2007

Vol. 81, nr 11

1899-1909

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.

Efficient synthesis of lactoneo series antigen lewis Y (LeY)

Hummel G., Schmidt R.

Polish Journal of Chemistry

1999

vol. 73 nr 6

941-954

The synthesis of glycosphingolipid Lewis Y (1) could be efficiently carried out, based on the connection of building blocks 2-7. Reaction of fucosyl donor 2 with azidoglucose derivative 4 as acceptor gave a(1-3)-linked disaccharide 8, which was transformed to acceptor 9; ensuing reaction with galactosyl donor 3 furnished Lewis X trisaccharide derivative 10. This compound could be transformed into the LeY hexasaccharide 16 either via transformation into glycosyl donor 12, connection with lactose moiety 5, and then reaction with fucosyl donor 2a, or, alternatively by transformation of 10 into acceptor 18, reaction with fucosyl donor 2, and then attachments of lactose moiety 5. Application ot the azidosphingosine glycosylation procedure to 16, i.e. first transformation into O-acyl protected hexaosyl donor 33, then reaction eith azidosphingosine 6 and fatty acid (7), and finally O-acyl deprotection, afforded target molecule 1 in high purity.