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Updated: Jun 24, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Chemoenzymatic synthesis of a new class of macrocyclic oligosaccharides
Saddam Muthana1, Hai Yu, Hongzhi Cao
1Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Abstract:
A novel and highly efficient chemoenzymatic method has been developed for the preparation of structurally defined macrocyclic oligosaccharides of varied sizes. This method involves chemical or chemoenzymatic synthesis of oligosaccharides containing a galactose at the nonreducing end and a propargyl group at the reducing end as sialyltransferase acceptors. Introducing an azido-containing sialic acid to the nonreducing end of the galactosides through a sialyltransferase-catalyzed enzymatic reaction followed by copper(I)-catalyzed Huisgen's 1,3-dipolar cycloaddition of alkyne and azide provides size-defined macrocyclic carbohydrates. The produced negatively charged macrocycles have high solubility in water and interact with hydrophobic small molecules in a size-dependent manner.
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