Synthesis of mono- and di-sialophospholipids via the H-phosphonate approach

Abstract

To overcome their inherent instability, stable modified mono- and di-sialophospholipids of the group C meningococcal polysaccharide were synthesized. Stability was achieved by introducing a spacer between the sialic acid residue and the phospholipid component, and by replacing the native ester linkages to the lipid by ether linkages. Mono- and di-hydroxylethylenesialosides were coupled to phosphoglyceroldietherlipid using H-phosphonate chemistry to give the anomerically pure sialophospholipids in good yields.Key words: polysialic acid, glycolipid, H-phosphonate, meningococcus.