期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 6, 页码 1632-1637出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809928
关键词
glycoprotein synthesis; glycosynthase; hexosaminidase; thioglycoligase; thioglycosides
资金
- Canadian Institutes for Health Research (CIHR)
- Canadian Glycoscience Network GlycoNet
- Schroedinger fellowship from the Austrian Science Fund (FWF)
Thioglycosides are hydrolase-resistant mimics of O-linked glycosides that can serve as valuable probes for studying the role of glycosides in biological processes. The development of an efficient, enzyme-mediated synthesis of thioglycosides, including S-GlcNAcylated proteins, is reported, using a thioglycoligase derived from a GH20 hexosaminidase from Streptomyces plicatus in which the catalytic acid/base glutamate has been mutated to an alanine (SpHex E314A). This robust, easily-prepared, engineered enzyme uses GlcNAc and GalNAc donors and couples them to a remarkably diverse set of thiol acceptors. Thioglycoligation using 3-, 4-, and 6-thiosugar acceptors from a variety of sugar families produces S-linked disaccharides in nearly quantitative yields. The set of possible thiol acceptors also includes cysteine-containing peptides and proteins, rendering this mutant enzyme a promising catalyst for the production of thio analogues of biologically important GlcNAcylated peptides and proteins.
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