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While sialylated carbohydrates represent attractive targets for anticancer vaccines, structural and antigenic insights into glycopeptides are still hampered by limited access to well\u2010defined structures, rendering their immunogenicity unclear. Herein, we describe an efficient chemoenzymatic platform for facile synthesis of a glycopeptide library comprising 18 structures with diverse\n                    <jats:italic>O<\/jats:italic>\n                    \u2010glycans at different glycosylation sites. Glycopeptide microarray\u2010based serological screening revealed a consistent preference of cancer patient sera for sialylated glycopeptides over their non\u2010sialylated counterparts. Motivated by this finding, we performed systematic immunological evaluations of sialylated and non\u2010sialylated glycopeptide\u2010tetanus toxoid (TT) conjugates, demonstrating that sialylated glycopeptide\u2010TT conjugates elicit stronger antibody responses, enhanced tumor cell recognition, and more potent tumor growth inhibition through synergistic activation of antigen\u2010presenting cells and T cell subsets. Furthermore, we developed a multicomponent cocktail vaccine by incorporating four sialylated glycopeptides, which elicited broader and more potent immune activation than single\u2010antigen formulations. Antisera from the cocktail vaccine exhibited strong binding to human tumor tissues, underscoring the clinical relevance of our findings. This work establishes sialylation as a key determinant of glycopeptide immunogenicity and provides a rational strategy for developing next\u2010generation glycopeptide\u2010based cancer vaccines.\n                  <\/jats:p>","DOI":"10.1002\/anie.202525026","type":"journal-article","created":{"date-parts":[[2026,1,19]],"date-time":"2026-01-19T13:03:01Z","timestamp":1768827781000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Chemoenzymatic Synthesis of Glycopeptide Library Decodes Sialylation\u2010Dependent Immunodominance to Enable a Potent Multicomponent Antitumor Vaccine"],"prefix":"10.1002","volume":"65","author":[{"given":"Ye","family":"Wu","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences (Shenzhen) Shenzhen Campus of Sun Yat\u2010Sen University  Shenzhen Guangdong 518107 China"},{"name":"State Key Laboratory of Chemical Biology Carbohydrate\u2010Based Drug Research Center 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