Chemical synthesis of glycopeptide related to T. cruzi and cancer mucins

Chemical synthesis of glycopeptide related to T. cruzi and cancer mucins

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

Abstract:

Mucins are highly O-glycosylated (about 60% carbohydrate by weight), glycoproteins that are rich in serine (Ser) and threonine (Thr) repeating units, whose external oligosaccharides are linked to the protein via sugar units of _-N-acetyl-glucosamine (GlcNAc), in T. cruzi, or _-N-acetylgalactosamine (GalNAc), in mammals. 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 cancer-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 of the glycopeptide NH2[_Gal]-(Thr)2- [_GalNAc]-(Thr)2-[_GlcNAc]-(Thr)3GlyOH 1, related to T. cruzi and cancer mucins, which can be useful for development of new therapeutics, like vaccines, against infectious and tumoral processes.

Mucins are highly O-glycosylated (about 60% carbohydrate by weight), glycoproteins that are rich in serine (Ser) and threonine (Thr) repeating units, whose external oligosaccharides are linked to the protein via sugar units of _-N-acetyl-glucosamine (GlcNAc), in T. cruzi, or _-N-acetylgalactosamine (GalNAc), in mammals. 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 cancer-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 of the glycopeptide NH2[_Gal]-(Thr)2- [_GalNAc]-(Thr)2-[_GlcNAc]-(Thr)3GlyOH 1, related to T. cruzi and cancer mucins, which can be useful for development of new therapeutics, like vaccines, against infectious and tumoral processes.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0113-1

Referências bibliográficas

• [1] 1 Buscaglia, C. A.; Campo, V. A.; Frasch, A. C. C.; DiNoia, J. M. Nat. Rev. Microbiol. 2006, 4, 229.
• [2] 2 Brocke, C.; Kunz, H. Bioorg. Med. Chem. 2002, 10, 3085.
• [3] 3 Campo, V. L.; Carvalho, I.; Allman, S.; Davis, B. G.; Field, R. A. Org. Biomol. Chem. 2007, 5, 2645.

Como citar:

Campo, Vanessa Leiria; Carvalho, Ivone; Baruffi, Marcelo Dias; "Chemical synthesis of glycopeptide related to T. cruzi and cancer mucins", p-113-113. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0113-1