Chapter 15: Polyester functionalized carbohydrates via organocatalyzed ring-opening polymerization
Published:20 Mar 2014
Y. Miao, A. Mortreux, and P. Zinck, in Carbohydrate Chemistry: Chemical and Biological Approaches, Volume 40, ed. A. Pilar Rauter, T. Lindhorst, and Y. Queneau, The Royal Society of Chemistry, 2014, vol. 40, ch. 15, pp. 298-311.
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The functionalization of carbohydrates with aliphatic biocompatible and biodegradable polyesters such as polylactides and polylactones leads to a great variety of structures useful for applications in the fields of medicine, biotechnology and materials science notably. One of the preferred strategies for this purpose is the carbohydrate initiated ring-opening polymerization of cyclic esters, due to its controlled character. Metals, enzymes and organic molecules mediated ring-opening polymerizations have been reported for this purpose. Metal catalysts can be found as residues in the resulting material, which can hamper its use for specific applications. Enzymes are powerful catalysts for the ring-opening polymerization of ɛ-caprolactone, but scarcely polymerize lactide. Organocatalysis is thus an interesting alternative in this frame. Recent advances in the functionalization of monosaccharides, cyclodextrins and polysaccharides via organocatalyzed ring-opening polymerization are reported, highlighting new reactivities and yielding new structures.