Synthetic multivalent ligands for cholera & cholera-like toxins: Protected cyclic neoglycopeptides

• Synthesis of a set of protected neoglycopeptides are reported.
• They include di-, tri-, tetra- & pentavalent scaffolds bearing upto 10 sugar units.
• Intended to derive potential inhibitors for cholera toxin/other analogous proteins.
• Sugars are attached by glycosylation to cyclic/acyclic backbone structures.

Synthesis of a set of novel glycopeptide analogues as potential cholera/cholera-like toxin inhibitors in their protected form is described. They include di-, tri-, tetra- and pentavalent scaffolds. The synthetic steps were achieved using a combination of solvent-free mechanochemical as well as the conventional solution-phase reactions. During the conventional DIC-HOBt-mediated peptide coupling followed for the preparation of certain glycopeptide analogues an interesting in situ Fmoc deprotection was observed which has been demonstrated to hold potential for synthesiszing glycopeptides/neoglycopeptides with extended polyamide chains.

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