Year: 2025
Type: article
Abstract: Pharmaceuticals, such as the antibiotic erythromycin, and sodium-dependent glucose transporter (SGLT1 & SGTL2) inhibitors such as Bexagliflozin (diabetes) and Sotagliflozin (heart disease), are often sugar-decorated (glycosylated). Glycosylation is a key component of the binding motif in SGLT inhibitors and, in natural products, glycosylation often confers improved bioactivity and bioavailability. Whilst a single C-glycoside link between a sugar moiety and its aglycone core is a common feature in natural products isolated to date, only a small number, including the antibiotics granaticin and sarubicin, are covalently bonded twice to a single sugar moiety. The way in which this “double C-glycosylation” is naturally mediated is not yet known, yet has been speculated on. Here, we report the exploration and development of a potentially biomimetic procedure that utilises intermolecular cycloaddition chemistry to access new “double C-glycosylated” products and enables the creation of bridged polycyclic ethers from a common maltol-derived oxidopyrylium salt precursor.
Source: Biomolecules
DOI: 10.3390/biom15060905
Authors: Kevin P. P. Mahoney, Rosemary Lynch, Rhea T. Bown, Sunil V. Sharma, Piyasiri Chueakwon, G. Richard Stephenson, David B. Cordes, Alexandra M. Z. Slawin, Rebecca J. M. Goss
Institutions: University of East Anglia, University of St Andrews
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,258
Awards: X-Genix: Translating precision molecular editing as a tool for drug discovery, Molecular X-Factor & SynBioFilms, G4879697178, European Marine Biological Research Infrastructure Cluster to promote the Blue Bioeconomy, GenoChemetics: Gene eXpression enabling selective Chemical functionalisation of natural products
OpenAlex ID: W4411451621