Journal
CARBOHYDRATE RESEARCH
Volume 467, Issue -, Pages 23-32Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2018.07.005
Keywords
Mannnose-6-phosphate; Glycosylation; Regioselective; Oligosaccharide
Funding
- National Science Foundation [CHE 1402744]
- National Institutes of Health (SBIR) [HHSN261201500020C]
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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.
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