Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to α(2,3)-sialylated glycans.

Richard J Fair,Heung Sik Hahm,Peter H Seeberger

doi:10.1039/c5cc01368b

Abstract

A synthetic strategy combining automated solid-phase chemical synthesis and enzymatic sialylation was developed to access α(2,3)-sialylated glycans.

Highlights

A synthetic strategy combining automated solid-phase chemical synthesis and enzymatic sialylation was developed to access a(2,3)-sialylated glycans
N-Acetyl-neuraminic acid (Neu5Ac) is the most studied among the over 50 sialic acids described to date and is a component of many glycans of biological relevance. a(2,6)-Sialylated and a(2,3)silylated glycans are predominantly found in nature
A sialic acid monosaccharide building block proved useful in producing a(2,6)-sialylated glycans.19 a(2,3)-Silylated glycans were formed in low yields (o20%) using this method

Summary

Introduction

Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to a(2,3)-sialylated glycans† A synthetic strategy combining automated solid-phase chemical synthesis and enzymatic sialylation was developed to access a(2,3)-sialylated glycans. Sialic acid-galactose disaccharide building blocks were used to produce a(2,3)- and a(2,6)-sialylated glycans by automated solid-phase synthesis.18 a Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476

Results

Conclusion