CHEMICAL SYNTHESIS OF THE GLYCOPEPTIDE NHAcpGAL-(1,3)-αGALNAc-THR3-αLACNAc-THR3-GLY-OVA RELATED TO T. CRUZI AND TUMOR MUCINS

摘要

Mucins are highly O-glycosylated glycoproteins that are rich in serine and threonine repeating units, whose external oligosaccharides are linked to the protein via sugar units of α-N-acetyl-glucosamine (GlcNAc), in T. cruzi, or α-N-acetylgalactosamine (GalNAc), in mammals [1]. In T. cruzi, these structures helps the parasite to interact with the infected host, while in vertebrates the functions of mucins range from being protective barriers to providing lubrication for epithelial cells. In tumor-related mucins, however, altered glycosylation is a common feature, being verified the presence of mono- and disaccharide structures known as T_n and TF antigens, respectively [1,2]. Therefore, this work presents the synthesis of the glycopeptide NHAc[βGal-(1,3)-aGalNAc]-Thr3-[αLacNAc]-Thr3-Gly-OVA 1 (Figure 1), related to T. cruzi and tumor mucins, which can be useful for development of new therapeutics, like vaccines, against infectious and tumoral processes.