Organic & Biomolecular Chemistry (2023): “Glycosyl Benzoates as Novel Substrates for Glycosynthases” 

Well done to Sabrina (our master student), Lauriane and Davey!


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.  ß-Glucosyl benzoate was hydrolysed by the GH1 ß-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 ß-glucosyl benzoate to the corresponding p-nitrophenyl- and thioglycosides.

Read the full paper here

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