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Synthesis of Unprecedented Sulfonylated Phosphono-exo-Glycals Designed as Inhibitors of the Three Mycobacterial Galactofuranose Processing Enzymes.
A new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate and was applied to eight different carbohydrates from the furanose and pyranose series, finding that the Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Expand
Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions
Abstract Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis ofExpand
A carbohydrate-based approach for the total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-Di-epi-dinemasone B.
The first total synthesis of (-)-dinemasone B is described, which features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from D-glucose. Expand
Synthetic polyprenol-pyrophosphate linked oligosaccharides are efficient substrates for mycobacterial galactan biosynthetic enzymes.
Results highlight the importance of the pyrophosphate motif in recognition of acceptor substrates by both enzymes and demonstrate a straightforward route for the preparation of such compounds and provide additional support for the process by which this important glycan is biosynthesized using, for the first time, close structural analogs to the natural substrates. Expand
Concise and direct construction of cis-pyrano[4,3-b]pyran-5-one skeleton from glucal derivatives: synthesis of ent-4-deoxy-2,3-di-epi-dinemasone BC
Abstract (−)-Dinemasones B and C were isolated from a culture of the endophytic fungus Dinemasporium strigosum and had shown attractive antimicrobial activities in vitro. Described herein is theExpand
Genetically Encoded, Multivalent Liquid Glycan Array (LiGA)
A LiGA platform comprising a library of DNA ‘barcoded’ M13 virions that display 30-1500 copies of glycans per phage is reported, which is target agnostic and can measure the glycan-binding profile of lectins such as CD22 on cells in vitro and immune cells in a live mouse. Expand
Genetically encoded multivalent liquid glycan array displayed on M13 bacteriophage
Liquid glycan arrays (LiGAs), presented on M13 bacteriophage surface proteins through bioorthogonal chemistry, link surface glycans to genetic barcodes in phage DNA, enabling lectin–glycan interaction profiling by DNA sequencing. Expand
Neoglycolipids as Glycosphingolipid Surrogates for Protein Binding Studies Using Nanodiscs and Native Mass Spectrometry.
The present work investigates the use of neoglycolipids (NGLs) as surrogates for GSLs for catch-and-release-electrospray ionization mass spectrometry (CaR-ESI-MS)-based screening, implemented with nanodiscs, for the discovery of GSL ligands. Expand