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Synthetic Glycopeptides for the Construction of Anticancer Vaccines

Glycopeptides of the tandem repeat region of the tumor-associated epithelial mucin MUC 1 containing tumor-associated saccharide antigens have been synthesized and conjugated to carrier proteins or T-cell epitope peptides. The T, sialyl T N , 2,6- and 2,3-sialyl T antigen amino acid building blocks were obtained by biomimetic syntheses starting from the monosaccharide T N antigen conjugate. To synthesize the MUC1 glycopeptides solid-phase methods with varied anchors were applied. Conjugation of synthetic glycopeptides to bovine serum albumin were achieved by selective reactions at squaric esters. Solid-phase fragment condensation proved successful for constructions of MUC1 glycopeptide-T-cell epitope conjugates. Immunization of mice with a synthetic vaccine consisting of a MUC1 glycopeptide and a T-cell epitope from ovalbumin induced a specific immune response. The elicited antibody only reacted with the glycopeptide. Neither its peptide nor the glycan in a different peptide were recognized. This precise differentiation by antibodies induced by chemically pure vaccines is considered promising for the development of antitumor vaccines.