ChemInform Abstract: Chemoenzymatic Synthesis of Sialylated Glycopeptides Derived from Mucins and T-Cell Stimulating Peptides

Autor: Henrik Clausen, Jan Kihlberg, Tilo Schwientek, Bjoern Holm, Celso A. Reis, Shaji K. George
Rok vydání: 2010
Předmět:
Zdroj: ChemInform. 33
ISSN: 1522-2667
0931-7597
Popis: The Tn, T, sialyl-Tn, and 2,3-sialyl-T antigens are tumor-associated carbohydrate antigens expressed on mucins in epithelial cancers, such as those affecting the breast, ovary, stomach, and colon. Glycopeptides carrying these antigens are of interest for development of cancer vaccines and a short, chemoenzymatic strategy for their synthesis is reported. Building blocks corresponding to the Tn (GalNAcα-Ser/Thr) and T [Galβ(1→3)GalNAcα-Ser/Thr] antigens, which are relatively easy to obtain by chemical synthesis, were prepared and then used in the synthesis of glycopeptides on the solid phase. Introduction of sialic acid to give the sialyl-Tn [Neu5Acα(2→6)GalNAcα-Ser/Thr] and 2,3-sialyl-T [Neu5Acα(2→3)Galβ(1→3)GalNAcα-Ser/Thr] antigens is difficult when performed chemically at the building block level. Sialylation was therefore carried out with recombinant sialyltransferases in solution after cleavage of the Tn and T glycopeptides from the solid phase. In the same manner, the core 2 trisaccharide [Galβ1→3(Gl...
Databáze: OpenAIRE
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