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Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage

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Abstract

As part of a program to explore the structural requirement of N-glycans in the carbohydrate-mediated biological interactions, N-linked pentasaccharide core structure was stereochemically modified in terms of glycosidic linkage. Three isomers, α-D-Man-(1→3)-[α-D-Man-(1→6)]-α-D-Man-(1→4)-β-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, α-D-Man-(1→3)-[α-D-Man-(1→6)]-β-D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, and α-D-Man-(1→3)-[α-D-man-(1→6)]-α-D-Man-(1→4)-α-D-GlcNAc-(1→4)-β-D-GlcNAc-L-Asn, were synthesized. Synthesis of the pentasaccharide with natural linkage is also described.

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Takatani, M., Nakama, T., Kubo, K. et al. Synthesis of N-linked pentasaccharides with isomeric glycosidic linkage. Glycoconj J 17, 361–375 (2000). https://doi.org/10.1023/A:1007151913476

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