Assembly of a series of malarial glycosylphosphatidylinositol anchor oligosaccharides |
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Authors: | Kwon Yong-Uk Soucy Regina L Snyder Daniel A Seeberger Peter H |
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Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA. |
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Abstract: | We report an efficient and convergent synthesis of a series of oligosaccharides comprised of the malaria GPI glycan (2a), a promising anti-malaria vaccine candidate currently in preclinical trials and several related oligosaccharide sequences (3-8) that are possible biosynthetic precursors of the malarial GPI. A flexible synthetic strategy is disclosed that relies on a late-stage coupling between oligomannosides of varying length and pseudo-disaccharide glycosyl acceptor 11 to readily access various malarial GPI structures. Phosphorylation was accomplished by mild and efficient H-phosphonate chemistry before the final deprotection was carried out by using sodium in ammonia. The direct connection of a thiol group via a phosphate diester linkage to the inositol moiety provides a handle for easy conjugation of the GPI glycan to carrier proteins, immobilization on carbohydrate microarrays and photo-affinity labels identification. These synthetic oligosaccharides will serve as molecular probes. |
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Keywords: | carbohydrates glycosylation malaria oligosaccharides vaccines |
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