Halogen-directed chemical sialylation: pseudo-stereodivergent access to marine ganglioside epitopes
Taiki Hayashi, Alexander Axer, Gerald Kehr, Klaus Bergander, Ryan Gilmour
Abstract
-glycolyl units common to marine Neu2,6Glu epitopes enables pseudo-stereodivergent sialylation. α-Selective sialylation results from fluorination, whereas traceless bromine-guided sialylation generates the β-adduct. This concept is validated in the synthesis of HLG-1 and Hp-s1 analogues.
Topics & Concepts
GangliosideSialic acidEpitopeHalogenChemistryGlycanBiochemistryStereochemistryComputational biologyBiologyGlycoproteinOrganic chemistryImmunologyAntigenAlkylCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchProteoglycans and glycosaminoglycans research