Synthesis of a beta1,2-mannopyranosyl tetrasaccharide found in the phosphomannan antigen of Candida albicans.
The synthesis of a portion of the challenging beta1,2-mannosyl polymer found in the cell walls of Candida albicans was undertaken to develop a conjugate vaccine against C. albicans and to facilitate NMR conformational studies of this unique polysaccharide. The novel approach to the synthesis of tetrasaccharide 1 employed the modified ulosyl bromide 11 as the glycosyl donor which provided high diastereoselectivity. A participating solvent as well as p-chlorobenzyl protection facilitated the new approach.
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Department of Chemistry, University of Alberta, Edmonton, AB, Canada T6G 2G2.
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D000946:Antigens, Fungal / Q000737:chemistry* / Q000276:immunology; D002176:Candida albicans / Q000276:immunology*; D002240:Carbohydrate Sequence; D005657:Fungal Vaccines / Q000138:chemical synthesis; D008351:Mannans / Q000138:chemical synthesis / Q000276:immunology; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000276:immunology; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000276:immunology; D013237:Stereoisomerism; D018074:Vaccines, Conjugate / Q000737:chemistry
D000946:Antigens, Fungal; D005657:Fungal Vaccines; D008351:Mannans; D011134:Polysaccharides; D018074:Vaccines, Conjugate; C005437:phosphomannan; D008358:Mannose