Synthesis of antifungal vaccines by conjugation of β-1,2 trimannosides with T-cell peptides and covalent anchoring of neoglycopeptide to tetanus toxoid.
Carbohydrate Research(2015)
摘要
•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.
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关键词
Glycoconjugate vaccine,Glycopeptide tetanus toxoid conjugate,Synthesis of glycopeptide,Thiol thioester exchange
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