Glycosyl benzoates as novel substrates for glycosynthases.
Org Biomol Chem
; 21(31): 6356-6359, 2023 08 09.
Article
en En
| MEDLINE
| ID: mdl-37486039
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. 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.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Tioglicósidos
/
Benzoatos
Idioma:
En
Año:
2023
Tipo del documento:
Article