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
