Synthesis of glycopeptides mimetics of T. cruzi and tumor mucins as potential vaccines

Synthesis of glycopeptides mimetics of T. cruzi and tumor mucins as potential vaccines

Campo, Vanessa Leiria; Baruffi, Marcelo Dias; Carvalho, Ivone

Abstract:

Mucins are highly O-glycosylated glycoproteins that are rich in serine (Ser) and threonine (Thr) repeating units, whose external oligosaccharides are linked to the protein via sugar units of α-N-acetylglucosamine (GlcNAc), in T. cruzi, or α-N-acetylgalactosamine (GalNAc), in mammals. In T. cruzi, these structures help the parasite to interact with the infected cell, 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 TN and TF antigens, respectively. Therefore, this work presents the synthesis and biological assays of the glycopeptides NHAc[βGal]-(Thr)2-[αGalNAc]-(Thr)2-[αGlcNAc] (Thr)2Gly-OVA 1 and NHAc[βGal-αGalNAc]-(Thr)3- [αLacNAc]-(Thr)3-Gly-OVA 2 related to T. cruzi and tumor mucins, which can be useful for development of vaccines against infectious and tumoral processes.

Mucins are highly O-glycosylated glycoproteins that are rich in serine (Ser) and threonine (Thr) repeating units, whose external oligosaccharides are linked to the protein via sugar units of α-N-acetylglucosamine (GlcNAc), in T. cruzi, or α-N-acetylgalactosamine (GalNAc), in mammals. In T. cruzi, these structures help the parasite to interact with the infected cell, 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 TN and TF antigens, respectively. Therefore, this work presents the synthesis and biological assays of the glycopeptides NHAc[βGal]-(Thr)2-[αGalNAc]-(Thr)2-[αGlcNAc] (Thr)2Gly-OVA 1 and NHAc[βGal-αGalNAc]-(Thr)3- [αLacNAc]-(Thr)3-Gly-OVA 2 related to T. cruzi and tumor mucins, which can be useful for development of vaccines against infectious and tumoral processes.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013819161927

Referências bibliográficas

• [1] 1 Brocke, C.; Kunz, H. Bioorg. Med. Chem. 2002, 10, 3085.
• [2] 2 Campo, V. L.; Carvalho, I.; Allman, S.; Davis, B. G.; Field, R. A. Org.
• [3] Biomol. Chem. 2007, 5, 2645.

Como citar:

Campo, Vanessa Leiria; Baruffi, Marcelo Dias; Carvalho, Ivone; "Synthesis of glycopeptides mimetics of T. cruzi and tumor mucins as potential vaccines", p-178-178. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013819161927