Caprolactone Carbohydrates

Li, BG Zhang, LM. Synthesis and characterization of novel amphiphilic block copolymers based on maltoheptaose and poly(e-caprolactone). Carbohydrate Polymers, 2008, 74, 390-395. 

In some sugar-based lactones, the carbohydrate moiety can serve as a chiral template. For example, the synthesis and characterisation of a novel chiral bicyclic caprolactone 1 was reported in 2003 in six steps from 1,2,5,6-di-O-isopropylidene-a-D-glucofuranose.10 The introduction of... 

Aldonolactones serve as suitable monomers for the generation of homo- and copolymers, especially through ring-opening polymerization (ROP). Among them are the carbohydrate-analogs of s-caprolactone, i.e., aldono-1,6-lactones. The first example of such derivatives and further ROP was reported by Galbis and co-workers [61], see also chapter, Synthetic polymers from readily available monosaccharides ... 

Zhao, S., Cao, M., Li, H., Li, L., Xu, W. Synthesis and characterization of thermosensitive semi-ipn hydrogels based on poly(ethylene glycol)-co-poly(epsilon-caprolactone) macromer, n-isopropylacrylamide, and sodium alginate. Carbohydrate Research 345, 425 31 (2010)... 

Aliphatic polyesters are biocompatible and biodegradable polymers that are widely used in biomedical applications. Within these, polylactides and poly(s-caprolactone) are two of the most studied ones (Fig. 2). These polyesters can be synthesized via ring-opening polymerization of the corresponding cyclic esters (s-caprolactone and lactide) and via polycondensation of lactic acid. In material science, both pure aliphatic polyesters and natural polysaccharides have limitations in some specific applications. These limitations can be overcome by the introduction of hydrophilic groups (carbohydrate compounds) into the aliphatic polyesters and modifications of natural polysaccharides with hydrophobic polyesters. 

Biodegradation of poly(3-caprolactone)/starch blends and composites in composting and culture environments the effect of compatibilization on the inherent biodegradability of the host polymer. Carbohydr. Res., 338 (17), 1759-1769. 

The ROP of lactones can also be achieved by the application of much milder organic acids. Several reports have detailed the ROP of e-caprolactone and 8-valerolactone where the polymerization has been catalyzed by additional lactic add [52, 53], fumaric acid [44], maleic add [44], tartaric acid [52], dtric add [52] and a range of amino acids [52, 54]. Tartaric acid was shown to the most active catalyst for the ROP of e-caproladone in a comparative study performed by Cordova and colleagues [52], The application of this methodology, in which the polymerizations are carried out in neat lactone at either 120 or 160 °C, results in the synthesis of polymers with molecular weights that agreed weU with the initial monomer initiator ratio, and with polydispersities ranging from 1.2 to 1.9. Extension to the synthesis of dendrimers such as star poly(ester)s [55] and the polymerization of e-caprolactone from carbohydrates [56] has also been reported. 

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