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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 mu...

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Detalles Bibliográficos
Autores principales: de Lorenzo, Sabrina, Pillet, Lauriane, Lim, David, Paradisi, Francesca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10410497/
https://www.ncbi.nlm.nih.gov/pubmed/37486039
http://dx.doi.org/10.1039/d3ob00979c
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author de Lorenzo, Sabrina
Pillet, Lauriane
Lim, David
Paradisi, Francesca
author_facet de Lorenzo, Sabrina
Pillet, Lauriane
Lim, David
Paradisi, Francesca
author_sort de Lorenzo, Sabrina
collection PubMed
description 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.
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spelling pubmed-104104972023-08-10 Glycosyl benzoates as novel substrates for glycosynthases de Lorenzo, Sabrina Pillet, Lauriane Lim, David Paradisi, Francesca Org Biomol Chem Chemistry 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. The Royal Society of Chemistry 2023-07-19 /pmc/articles/PMC10410497/ /pubmed/37486039 http://dx.doi.org/10.1039/d3ob00979c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
de Lorenzo, Sabrina
Pillet, Lauriane
Lim, David
Paradisi, Francesca
Glycosyl benzoates as novel substrates for glycosynthases
title Glycosyl benzoates as novel substrates for glycosynthases
title_full Glycosyl benzoates as novel substrates for glycosynthases
title_fullStr Glycosyl benzoates as novel substrates for glycosynthases
title_full_unstemmed Glycosyl benzoates as novel substrates for glycosynthases
title_short Glycosyl benzoates as novel substrates for glycosynthases
title_sort glycosyl benzoates as novel substrates for glycosynthases
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10410497/
https://www.ncbi.nlm.nih.gov/pubmed/37486039
http://dx.doi.org/10.1039/d3ob00979c
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AT paradisifrancesca glycosylbenzoatesasnovelsubstratesforglycosynthases