Issue 1, 2021

Synthetic glycosidases for the precise hydrolysis of oligosaccharides and polysaccharides

Abstract

Glycosidases are an important class of enzymes for performing the selective hydrolysis of glycans. Although glycans can be hydrolyzed in principle by acidic water, hydrolysis with high selectivity using nonenzymatic catalysts is an unachieved goal. Molecular imprinting in cross-linked micelles afforded water-soluble polymeric nanoparticles with a sugar-binding boroxole in the imprinted site. Post-modification installed an acidic group near the oxygen of the targeted glycosidic bond, with the acidity and distance of the acid varied systematically. The resulting synthetic glycosidase hydrolyzed oligosaccharides and polysaccharides in a highly controlled fashion simply in hot water. These catalysts not only broke down amylose with similar selectivities to those of natural enzymes, but they also could be designed to possess selectivity not available with biocatalysts. Substrate selectivity was mainly determined by the sugar residues bound within the active site, including their spatial orientations. Separation of the product was accomplished through in situ dialysis, and the catalysts left behind could be used multiple times with no signs of degradation. This work illustrates a general method to construct synthetic glycosidases from readily available building blocks via self-assembly, covalent capture, and post-modification. In addition, controlled, precise, one-step hydrolysis is an attractive way to prepare complex glycans from naturally available carbohydrate sources.

Graphical abstract: Synthetic glycosidases for the precise hydrolysis of oligosaccharides and polysaccharides

Supplementary files

Article information

Article type
Edge Article
Submitted
25 sep 2020
Accepted
20 okt 2020
First published
05 nov 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 374-383

Synthetic glycosidases for the precise hydrolysis of oligosaccharides and polysaccharides

X. Li and Y. Zhao, Chem. Sci., 2021, 12, 374 DOI: 10.1039/D0SC05338D

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