Synthesis of High-mannose Oligosaccharides Containing Mannose-6-phosphate Residues Using Regioselective Glycosylation

Overview

Journal Carbohydr Res

Publisher Elsevier

Specialties Biochemistry
Endocrinology

Date 2018 Aug 4

PMID 30075362

Citations 1

Authors

Bo Meng

Jun Wang

Quanli Wang

Anthony S Serianni

Qingfeng Pan

Affiliations

Soon will be listed here.

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.

Citing Articles

A convenient synthesis of short-chain α-(1 → 2) mannopyranosyl oligosaccharides.

Zhang W, Wang J, Serianni A, Pan Q Carbohydr Res. 2020; 489:107897.

PMID: 32092558 PMC: 7191533. DOI: 10.1016/j.carres.2019.107897.

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