"Click" Glycodendrimers Containing 27, 81, and 243 Modified Xylopyranoside Termini

Jérémy Camponovo (1) , Caroline Hadad (2) , Jaime Ruiz (1) , Eric Cloutet (3, 4) , Sylvain Gatard (2) , Jacques Muzart (2) , Sandrine Bouquillon (2) , Didier Astruc (1)

1 ISM - Institut des Sciences Moléculaires
2 URCA - Université de Reims Champagne-Ardenne
3 LCPO - Laboratoire de Chimie des Polymères Organiques
4 Team 4 LCPO : Polymer Materials for Electronic, Energy, Information and Communication Technologies

A series of large glycodendrimers containing 27, 81, and 243 terminal modified xylose branches from the first (G1-27) to the third generation (G3-243) were synthesized from 2′-azidoethyl 2,3,4-tri-O-acetyl--D-xylopyranoside and alkynyl-terminated dendrimers by "click" chemistry that is confirmed to be an excellent method to obtain large glycodendrimers exemplified by the use of modified xylose. The dendrimers were first characterized by 1H NMR, 13C{1H}NMR, elemental analysis, and IR spectroscopy. The size progression in the series was also demonstrated using both DOSY NMR and size exclusion chromatography (SEC), the latter technique showing the good polydispersity of all the dendrimers. The size measured by dynamic light scattering (DLS) for the dendrimer G3-243 is close to that obtained by the DOSY NMR method.

Mots clés: click; glycodendrimer; xylose

Domaines: Polymères

Jérémy Camponovo, Caroline Hadad, Jaime Ruiz, Eric Cloutet, Sylvain Gatard, et al.. "Click" Glycodendrimers Containing 27, 81, and 243 Modified Xylopyranoside Termini. Journal of Organic Chemistry, 2009, 74 (14), pp.5071-5074. ⟨10.1021/jo900554b⟩. ⟨hal-00400453⟩