Issue 31, 2023

Glycosyl benzoates as novel substrates for glycosynthases


The development of a procedure for the one-pot synthesis of glycosyl benzoates directly from unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolium chloride (DMC), thiobenzoic acid, and triethylamine is reported. These glycosyl donors are excellent substrates for wild-type and mutant glycosidases. β-Glucosyl benzoate was hydrolysed by the GH1 β-glucosidase derived from Halothermothrix orenii (HorGH1). Subsequent use of this substrate in thioligase-mediated glycosylation of p-nitrothiophenol demonstrated their superiority as donors compared to their p-nitrophenol counterparts with excellent conversions. Using a series of arene nucleophiles, we also demonstrate good to excellent conversions (up to 94%) of β-glucosyl benzoate to the corresponding p-nitrophenyl- and thioglycosides.

Graphical abstract: Glycosyl benzoates as novel substrates for glycosynthases

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Article information

Article type
20 Jun 2023
19 Jul 2023
First published
19 Jul 2023
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2023,21, 6356-6359

Glycosyl benzoates as novel substrates for glycosynthases

S. de Lorenzo, L. Pillet, D. Lim and F. Paradisi, Org. Biomol. Chem., 2023, 21, 6356 DOI: 10.1039/D3OB00979C

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