De Lorenzo, Sabrina; Pillet, Lauriane; Lim, David; Paradisi, Francesca (2023). Glycosyl Benzoates as Novel Substrates for Glycosynthases. Organic & biomolecular chemistry, 21(31), pp. 6356-6359. Royal Society of Chemistry 10.1039/D3OB00979C
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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.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
De Lorenzo Cardinal, Sabrina, Pillet, Lauriane, Lim, David, Paradisi, Francesca |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1477-0520 |
Publisher: |
Royal Society of Chemistry |
Funders: |
[4] Swiss National Science Foundation |
Projects: |
[UNSPECIFIED] Artificial Enzymatic Factories |
Language: |
English |
Submitter: |
Francesca Paradisi |
Date Deposited: |
24 Oct 2023 14:23 |
Last Modified: |
24 Oct 2023 14:32 |
Publisher DOI: |
10.1039/D3OB00979C |
PubMed ID: |
37486039 |
BORIS DOI: |
10.48350/184950 |
URI: |
https://boris.unibe.ch/id/eprint/184950 |
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