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Glycosyl benzoates as novel substrates for glycosynthases.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2023 Aug 09; Vol. 21 (31), pp. 6356-6359. Date of Electronic Publication: 2023 Aug 09. - Publication Year :
- 2023
-
Abstract
- 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 ( Hor GH1). 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.
- Subjects :
- Glycoside Hydrolases
Glycosylation
Benzoates
Thioglycosides
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 21
- Issue :
- 31
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 37486039
- Full Text :
- https://doi.org/10.1039/d3ob00979c