1021159-75-0Relevant academic research and scientific papers
Efficient synthesis of MUC4 sialylglycopeptide through the new sialylation using 5-acetamido-neuraminamide donors
Okamoto, Ryo,Souma, Shingo,Kajihara, Yasuhiro
, p. 3460 - 3466 (2008/09/20)
(Chemical Equation Presented) Sialylation reactions using a new sialyl donor, diethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-β-D- glycero-D-galacto-2-nonulopyranosylonamide phosphite (Neu5Ac-1-amide-2- phosphite) derivatives, and the synthesis of the sialyl-TN-MUC4 glycopeptide are described. The sialylation was performed in CH 2Cl2 solvent toward the 6-hydroxyl group of several monosugar acceptors and generated α-sialoside in good yield under low temperature and TMSOTf activation system. Amide derivatives of sialoside were easily converted into naturally occurring sialoside after hydrolysis of the amide group. Sialyl-α(2,6)-GalN3 was also prepared by this new sialylation protocol, and then this sialoside was further converted into a Fmoc-protected sialyl-TN serine derivative for solid-phase glycopeptides synthesis. The solid-phase glycopeptide synthesis using this sialyl-TN serine derivative in which the sugar hydroxyl group was free afforded the target sialyl-TN-MUC4 glycopeptide.
