Synthesis 2012; 44(11): 1647-1656
DOI: 10.1055/s-0031-1290975
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Triazole-Linked Fluorescent Saccharides and Glycosyl Amino Esters

Hua Yi
PPSM, ENS Cachan, CNRS, UMR 8531, 61 av. Président Wilson, 94235 Cachan cedex, France, Fax: +33(1)47402454   Email: joanne.xie@ens-cachan.fr
,
Stéphane Maisonneuve
PPSM, ENS Cachan, CNRS, UMR 8531, 61 av. Président Wilson, 94235 Cachan cedex, France, Fax: +33(1)47402454   Email: joanne.xie@ens-cachan.fr
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Juan Xie*
PPSM, ENS Cachan, CNRS, UMR 8531, 61 av. Président Wilson, 94235 Cachan cedex, France, Fax: +33(1)47402454   Email: joanne.xie@ens-cachan.fr
› Author Affiliations
Further Information

Publication History

Received: 25 January 2012

Accepted after revision: 24 March 2012

Publication Date:
09 May 2012 (online)


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.