Synthesis of glycosyl-amino acids of biological interest

摘要

This work describes the synthesis of the glycosylated amino acids αGlcNAc-Thr, βGlcNAc-Thr and αLacNAc-Thr by the glycosylation reaction of the amino acid threonine with the corresponding glycosyl donors αGlcNAcCl and αLacN3Cl. The glycosylated amino acids containing the sugar units α-D-GlcNAc and α-D-LacNAc O-linked to threonine amino acids are related to O-glycans found in mucins of the parasite Trypanosoma cruzi, while the corresponding β-D-GlcNAc isomer is involved in cellular signaling events.