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  • Title: First synthesis of the immunodominant beta-galactofuranose-containing tetrasaccharide present in the cell wall of Aspergillus fumigatus.
    Author: Fu M, Zhang G, Ning J.
    Journal: Carbohydr Res; 2005 Jan 17; 340(1):25-30. PubMed ID: 15620663.
    Abstract:
    beta-Galf-(1-->5)-beta-Galf-(1-->6)-alpha-Manp-(1-->6)-alpha-Manp, the immunodominant epitope in the cell-wall galactomannan of Aspergillus fumigatus, was synthesized for the first time as its allyl glycoside. The key disaccharide glycosyl donor, 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl-(1-->5)-2-O-acetyl-3,6-di-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate (10), was constructed by 5-O-glycosylation of 1,2-O-isopropylidene-3,6-di-O-benzoyl-alpha-D-galactofuranose (4) with 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetimidate (5), followed by 1,2-O-deacetonation, acetylation, selective 1-O-deacetylation, and trichloroacetimidation. The target tetrasaccharide 16 was obtained by the condensation of allyl 2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside (14) as glycosyl acceptor with the disaccharide glycosyl donor 10, followed by deprotection.
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