Synthetic Glycosidase Distinguishing Glycan and Glycosidic Linkage in Its Catalytic Hydrolysis.

ACS Catalysis
Xiaowei Li, Yan Zhao

Abstract

Selective hydrolysis of carbohydrates is vital to the processing of these molecules in biology but has rarely been achieved with synthetic catalysts. The challenge is especially difficult because the catalyst needs to distinguish the inversion of a single hydroxyl and the α or β glycosidic bonds that join monosaccharide building blocks. Here we report synthetic glycosidase prepared through molecular imprinting within a cross-linked micelle. The nanoparticle catalyst resembles natural enzymes in dimension, water-solubility, and a hydrophilic/hydrophobic surface-core topology. Its boronic acid-functionalized active site binds its targeted glycoside substrate and an acid cofactor simultaneously, with the acidic group in close proximity to the exocyclic glycosidic oxygen. The hydrophobically anchored acid cofactor is tunable in acidity and causes selective cleavage of the targeted glycoside in mildly acidic water. Selectivity for both the glycan and the α/β glycosidic bond can be rationally designed through the molecular imprinting process.

References

Jan 1, 1975·Advances in Enzymology and Related Areas of Molecular Biology·W P Jencks
Mar 28, 2001·Science·C R Bertozzi, L L Kiessling
Jan 10, 2002·Chemical Reviews·Günter Wulff
Sep 4, 2003·Chemistry : a European Journal·Marco Emgenbroich, Günter Wulff
Mar 10, 2005·Journal of the American Chemical Society·Fernando Ortega-CaballeroMikael Bols
Nov 3, 2005·Current Opinion in Structural Biology·Gideon J DaviesBernard Henrissat
Mar 30, 2006·Journal of the American Chemical Society·Meenakshi Dowlut, Dennis G Hall
Oct 1, 2009·Journal of the American Chemical Society·Kyoung Taek KimJan C M van Hest
Aug 20, 2011·Chemistry : a European Journal·Ania ServantMarina Resmini
Feb 22, 2012·Journal of the American Chemical Society·Hyunkyu KimKyoung Taek Kim
Nov 15, 2012·Accounts of Chemical Research·Steven D BullTony D James
Jul 19, 2013·Chemical Society Reviews·Xin WuYun-Bao Jiang
Aug 13, 2013·Journal of the American Chemical Society·Joseph K Awino, Yan Zhao
Dec 25, 2013·Chemical Society Reviews·Matthieu RaynalPiet W N M van Leeuwen
Jun 27, 2014·Chemical Communications : Chem Comm·Mousumi SamantaSubhajit Bandyopadhyay
Jul 28, 2016·The Journal of Organic Chemistry·M D Arifuzzaman, Yan Zhao
Oct 18, 2016·ACS Applied Materials & Interfaces·Xiantao ShenBörje Sellergren
Dec 15, 2016·Chemical Reviews·Krishnan K Palaniappan, Carolyn R Bertozzi
Dec 17, 2016·Journal of the American Chemical Society·Roshan W Gunasekara, Yan Zhao
Jan 28, 2017·Journal of the American Chemical Society·Joseph K AwinoYan Zhao
Mar 17, 2018·Biomacromolecules·Babloo Sharma, Susanne Striegler
Sep 24, 2019·The Journal of Organic Chemistry·Likun Duan, Yan Zhao
Aug 5, 2020·Chemical Communications : Chem Comm·Likun DuanYan Zhao
Jul 9, 2019·Chemistry of Materials : a Publication of the American Chemical Society·Shixin Fa, Yan Zhao

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Citations

Jun 1, 2021·Chembiochem : a European Journal of Chemical Biology·Yan Zhao
Jun 20, 2021·Advanced Materials·Maryam ArabiLingxin Chen

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