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Galectins are potential biomarkers and therapeutic targets. However, galectins display broad affinity towards β-galactosides meaning glycan-based (nano)biosensors lack the required selectivity and affinity. Using a polymer-stabilized nanoparticle biosensing platform, we herein demonstrate that the specificity of immobilised lacto--biose towards galectins can be 'turned on/off' by using site-specific glycan fluorination and in some cases reversal of specificity can be achieved. The panel of fluoro-glycans were obtained by a chemoenzymatic approach, exploiting BiGalK and BiGalHexNAcP enzymes from which are shown to tolerate fluorinated glycans, introducing structural diversity which would be very laborious by chemical methods alone. These results demonstrate that integrating non-natural, fluorinated glycans into nanomaterials can encode unprecedented selectivity with potential applications in biosensing.
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http://dx.doi.org/10.1039/d0sc05360k | DOI Listing |
JACS Au
August 2025
School of Chemical & Physical Sciences and Centre for Glycoscience, Keele University, Keele, Staffordshire ST5 5BG, U.K.
Fluorinated glycans offer a prime opportunity to study the intricacies of their associated binding events with proteins, invoke resistance toward enzymatic hydrolysis, and modulate carbohydrate physicochemical properties. Sugar nucleotides are the key building blocks used by glycosyltransferases and associated enzymes to assemble glycans and, as such, represent a considerable landscape of opportunity to develop fluorinated motifs and enable structure-to-function understanding. Herein, we target the isosteric inclusion of fluorine within the nucleoside diphosphate sugar framework of GDP-mannose using a chemoenzymatic approach.
View Article and Find Full Text PDFMed Oncol
August 2025
Centre for Research Impact & Outcome, Chitkara College of Pharmacy, Chitkara University, Rajpura, Punjab, India.
Chitosan, a naturally derived polysaccharide, has gained considerable attention as a biomaterial for drug delivery due to its excellent biocompatibility, biodegradability, and mucoadhesive properties. However, its limited solubility and compatibility with hydrophobic drugs restrict broader applications. Recent advances in the chemical modification of chitosan specifically through fluorination have significantly improved its performance in nanomedicine.
View Article and Find Full Text PDFOrg Lett
August 2025
Huazhong University of Science and Technology, Tongji Medical College, School of Pharmacy, Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Wuhan 430030, People's Republic of China.
Asperustins K-P (-), six unreported chlorinated austocystins, were isolated from NRRL 5856. Their structures, including absolute configurations, were elucidated by extensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction. Asperustin K () features an unprecedented carbon skeleton with a 6/6/6/5/5/6/6/6 fused octacyclic ring system, while asperustin L () represents a distinctive carbon skeleton with a 6/6/6/5/5/5 hexacyclic ring system.
View Article and Find Full Text PDFInt J Biol Macromol
September 2025
School of Biological and Chemical Engineering, Guangxi University of Science and Technology, Liuzhou 545006, China; Guangxi Key Laboratory of Green Processing of Sugar Resources, Liuzhou 545006, China. Electronic address:
Selective removal of F from industrial wastewater containing multiple anions is a major challenge. Here, we propose a biomimetic chitosan/FeOOH/AlOOH bead (CFeAlB) with a unique honeycomb porous structure and amino and hydroxyl multifunctional groups and AlOOH/FeOOH bimetallic active components for enhanced selective adsorption capacity and enrichment of F. The adsorption of F by CFeAlB (29.
View Article and Find Full Text PDFRSC Chem Biol
August 2025
Department of Chemistry, Indian Institute of Science Education and Research Pune 411008 India
Fluorinated carbohydrates are emerging scaffolds in glycobiology, enabling the elucidation of the roles of the individual hydroxyl groups of a carbohydrate in protein binding and drug discovery. Herein, we report a divergent strategy to synthesize seven heparan sulfate (HS) mimetics featuring a fluorine atom at the C3 position of the glucuronic acid residue, with the objective of modulating structure-function relationships. The sensitivity of fluorine signals to sulfation patterns was confirmed F-NMR spectroscopy, while coupling and NOE data demonstrated that the glucuronic acid residue retained its C conformation.
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