Synthesis of Triazole-Linked Fluorescent Saccharides and Glycosyl Amino Esters

Abstract

Synthesis of fluorescent carbohydrates and glycopeptides has been emerging as an attractive research field because of various biological roles of carbohydrates and glycoproteins. Fluorescent glycosides and C-glycosides were synthesized by copper(I)-catalyzed Huisgen reaction between 6-O-(2-azidoacetyl) glycopyranosides and alkyne-functionalized fluorophores. For the fluorescent disaccharides as well as glycosyl amino acids derivatives, glycosylation of azido-functionalized thioglycosides, followed by click reaction with corresponding fluorophores is preferred than the inversed procedure (click reaction before the glycosylation). Fluorophores like dansyl, NBD, or rhodamine have been successfully introduced on the sugar ring. All the newly synthesized fluorescent glycosides and glycoconjugates showed similar photophysical properties to the native fluorophores, with a higher quantum yield for the dansyl derivatives.

Key words

fluorescence - saccharides - glycosyl amino acids - copper(I) - Huisgen cycloaddition reaction - glycosylation

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