It is of great interest to obtain a method to conjugate peptides in a selective and efficient fashion. In our group we focus on oxime linker as aldehydes and ketones selectively react with hydroxylamine group forming a stable oxime bond in weak acidic conditions. The application of peptides conjugated through oxime bond is very broad as getting novel glycopeptides or polymer-peptide conjugate.

MUC1 is a mucin glycoprotein involves in many biological process and abnormal glycosylation has been observed in several cancer patients. In a first approach, we established a microarray platform based on oxime ligation. We designed and synthesized a library of glycopeptides, further we incorporated a ketone group at N-terminus to be linked to hydroxylamine linker on the surface of Glycan Array slides. In this work we will present an exhaustive study of MUC1 glycopeptide epitope library to be recognized by anti-MUC1 antibodies.

Further, another of our interests is related with small fragments of hyaluronic acid (HA) that can be recognized by TLR2 expressed in macrophages and dendritic cells. It has been observed that HA small fragments stimulates and promotes an immune response and its possible role as adjuvant is still unknown. Novel immunotherapies approaches include the injection of epitopes and adjuvants linked together to boost immune system. Based on this design, we synthesized a novel conjugated vaccine based on multiepitope peptide with a hydroxylamine group in N-terminal to be conjugated through the aldehyde of the open form of the reducing end of HA. 

In the present work we demonstrate the efficiency and versatility of oxime linker as a platform for construction of neo-conjugated peptides.