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1. (Article ID: 1066)
Ogawa Y, Lei PS, Kovác P
Synthesis of four glycosides of a disaccharide fragment representing the terminus of the O-polysaccharide of Vibrio cholerae O:1, serotype Inaba, bearing aglycons suitable for linking to proteins
Carbohydrate Research 288 (1996)
85-98
Methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside was converted into the crystalline 2-(trimethylsilyl)ethyl 4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside. Debenzoylation of the latter, followed by glycosylation of the resulting 2-hydroxy derivative with 2-O-acetyl-4-azido-4,6-dideoxy-α-D-mannopyranosyl chloride, gave the 2-(trimethylsilyl)ethyl glycoside of the corresponding disaccharide (8). Deacetylation of 8, followed by reduction of the resulting 4-azido-2-hydroxy derivative with H2S, gave the corresponding amine 10. The latter was treated with 4-O-benzyl-3-deoxy-L-glycero-tetronic acid to give, after debenzylation and acetylation, the fully protected 2-(trimethylsilyl)ethyl α-glycoside of the disaccharide fragment of the O-PS of Vibrio cholerae O:1, serotype Inaba (13). Compound 13 was transformed into the corresponding 1-trichloroacetimidate which was treated, separately, with methyl 6-hydroxy-hexanoate and 2-(2-methoxycarbonylethylthio)ethanol, to give two analogs of 13 possessing a differing linkage arm, namely the methyl esters 16 and 17. Each of 16 and 17 was treated with aqueous sodium hydroxide, followed by a cation-exchange resin, to give the two corresponding carboxylic acids (19 and 22). Alternately, treatment of 16 and 17 with hydrazine hydrate gave the acid hydrazides 20 and 23.
Lipopolysaccharide, synthesis, LPS, serotype, O-antigen, protein, O-polysaccharide, O polysaccharide, fragment, Vibrio, Vibrio cholerae, Vibrio cholerae O1, disaccharide, proteins, glycosides, glycoside, terminus, neoglycoconjugate, disaccharide epitope
NCBI PubMed ID: 8765728Journal NLM ID: 0043535Publisher: Elsevier
Institutions: NIDDK, National Institutes of Health, Bethesda, MD, USA
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