Synthesis of the Upstream Terminal Disaccharide of the O-Antigenic Polysaccharide of Vibrio cholerae O37 |
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Authors: | Koushik Mazumder Swarbhanu Sarkar Asish Kumar Sen |
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Affiliation: | Chemistry Division , CSIR-Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Jadavpur, Kolkata , 700032 , India |
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Abstract: | The terminal disaccharide of the O-antigenic polysaccharide of Vibrio cholerae O37, 4-O-methyl-α-D-QuiNAc-(1→4)-α-d-QuiNAc, was synthesized as methyl glycoside involving glycosylation between glycosyl donor ethyl 2-azido-3-O-benzyl-2,6-dideoxy-4-O-methyl-6-iodo-1-thio-α-d-glucopyranoside and glycosyl acceptor methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-d-glucopyranoside. Dehalogenation, global deprotection, and reduction of the azide to amine were effected in one step by catalytic hydrogenation. It was followed by selective N-acetylation to give the desired deprotected disaccharide. |
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Keywords: | Vibrio cholerae O37 O-Antigenic lipopolysaccharide Synthesis Upstream terminal disaccharide |
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