Conjugation-Amenable Tetrasaccharide of the Side Chain of the Major Glycoprotein of the Bacillus anthracis Exosporium: A Large-Scale Preparation

Abstract

A new strategy towards the synthesis of the title tetrasaccharide is described. The novelty within the common (2+2) assembly lies in the use of a disaccharide glycosyl donor having the fully assembled anthrose as one of the constituent sugar residues. Also, the final deprotection and transformation of the spacer arm into an amine, to form a structure amenable to conjugation by different conjugation techniques, is a one-pot conversion. Compared to other synthetic approaches, the present synthesis involves fewer chemical manipulations with the assembled tetrasaccharide as well as fewer overall numbers of synthetic steps towards this important antigenic component of a potential conjugate vaccine for anthrax.

Key words

carbohydrates - oligosaccharides - glycosylations - conjugation - amines

References

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