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A highly effective method for the synthesis of neoglycoconjugates has been developed. The technique is based on two steps. First, a sulfhydryl group is introduced into the carbohydrate by reductive amination with cysteamine, and secondly the sulfhydryl group carrying carbohydrate is coupled to a protein or carrier via a disulfide bridge. The method was used to couple sialic acid-containing carbohydrates such as N-acetylneuraminyllactose and the carbohydrate moieties of gangliosides (GM1, GM3 and GD1b) to bovine serum albumin. Biological functionality of the generated GM1- and GD1b-neoglycoprotein was demonstrated by a choleratoxin-binding assay and an immunoassay, respectively. The applicability of neoglycoconjugates for the quantification of gangliosides in solution by a competitive assay is shown.

biological chemistry hoppe-seyler

An Effective Method for the Synthesis of Neoglycoproteins and Neogangliosideproteins by Use of Reductively Aminated Sulfhydryl-Containing Carbohydrate Conjugates