Synthesis of high-mannose oligosaccharides containing mannose-6-phosphate residues using regioselective glycosylation. (September 2018)

• Record Type: Journal Article
• Authors: Meng, Bo; Wang, Jun; Wang, Quanli; Serianni, Anthony S.; Pan, Qingfeng
• Is Part Of: Carbohydrate research. Volume 467(2018)
• Page Start: 23
• Page End: 32
• Publication Date: 2018-09
• Subjects: Mannnose-6-phosphate -- Glycosylation -- Regioselective -- Oligosaccharide; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2018.07.005
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Molecular recognition of mannose-6-phosphate (M6P)-modified oligosaccharides by transmembrane M6P receptors is a key signaling event in lysosomal protein trafficking in vivo . Access to M6P-containing high-mannose N -glycans is essential to achieving a thorough understanding of the M6P ligand–receptor recognition process. Herein we report the application of a versatile and reliable chemical strategy to prepare asymmetric di-antennary M6P-tagged high-mannose oligosaccharides in >20% overall yield and in high purity (>98%). Regioselective chemical glycosylation coupled with effective phosphorylation and product purification protocols were applied to rapidly assemble these oligosaccharides. The development of this synthetic strategy simplifies the preparation of M6P-tagged high-mannose oligosaccharides, which will improve access to these compounds to study their structures and biological functions. Graphical abstract: Image 1 Highlights: One of few studies on synthesis of mannose-6-phosphate containing oligosaccharides, suitable for rapid library assembly. Complete 1D and 2D NMR analysis of mannose-6-phosphate containing oligosaccharides with high resolution. Combined column purification of mannose-6-phosphate containing oligosaccharides for high purity over 98%.