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Concise synthesis of the tetrasaccharide repeating unit of the O-antigen from Escherichia coli O131 containing N-acetyl neuraminic acid.

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Synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O131 was accomplished through a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The… Click to show full abstract

Synthesis of the tetrasaccharide repeating unit of the O-antigen from E. coli O131 was accomplished through a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging α-glycosylation of N-acetyl neuraminic acid was achieved through activation of thioglycoside using NIS-mediated glycosylation strategy. The target tetrasaccharide in the form of its 3-aminopropyl glycoside may be used for further glycoconjugate formation without hampering the anomeric stereochemistry.

Keywords: coli o131; acetyl neuraminic; unit antigen; repeating unit; tetrasaccharide repeating; synthesis tetrasaccharide

Journal Title: Carbohydrate research
Year Published: 2022

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