Organic Letters · 2023 · 40 citations · 21 references
PharmacyBiochemistryMedicinal ChemistryBioorthogonal ChemistryCarbohydrate ChemistryGlycobiologyBioconjugation ChemistryCarbohydrate ProtectionGlycosidic Bond FormationGlycosylation PathwaysChemical GlycosylationFree Radical AdditionGlycan SynthesisGlycoconjugate SynthesisGlycosylation BiocatalysisGlycosylation Method DevelopmentSubstrate ScopeSubstrate Scope Expansion
Herein, we report a method that enables the synthesis of carbohydrate-DNA conjugates by radical addition. Key to the success is the use of readily available, bench-stable, and unprotected glycosyl sulfinates as precursors to glycosyl radicals. The redox neutral reaction proceeds under mild and simple conditions and tolerates a broad substrate scope. A small library of carbohydrate-DNA conjugates was prepared.
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Philip A. Harris, Bryan W. King, Deepak Bandyopadhyay et al. · Journal of Medicinal Chemistry · 2016 · 275 citations · Full text