Synthesis of antifungal vaccines by conjugation of β-1,2 trimannosides with T-cell peptides and covalent anchoring of neoglycopeptide to tetanus toxoid

- Three component trisaccharide-peptide and carrier protein vaccines have been synthesized.
- Conjugation employed peptides bearing N-terminal thiols and acetylated C-terminal thiols.
- Thiol-thioester exchanged results in a mixture of glycopeptides bearing saccharides linked to N-terminal and C-terminal amino acids.
- Installation of an N-terminal thiol with a lower pKa ensured a single glycopeptide with an oligosaccharide installed at the N-terminus of the peptide.
- Replacement of the C-terminal thiol with an azido amino acid allowed 'click' chemistry to be used for attaching the glycopeptide to a protein carrier.