2017
DOI: 10.1002/cssc.201701870
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Complete Depolymerization and Repolymerization of a Sugar Poly(orthoester)

Abstract: The capability of a polymer to depolymerize, regenerating its original monomer for further polymerization, is very attractive in terms of sustainability. Recently discovered sugar poly(orthoesters) are an important class of glycopolymer. The high sensitivity of the backbone orthoester linkage toward acidolysis provides a valuable model to study the depolymerization. Herein, a sugar poly(orthoester) is shown to be completely depolymerized under acidic conditions. Interestingly, instead of the original monomer, … Show more

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Cited by 7 publications
(2 citation statements)
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“…8,29 Hydrolysis driven glycosidic bond (C-O-C) cleavage is well-known among carbohydrates and nucleic acids, rendering them an excellent drug-payload carrier in biological environments. [29][30][31][32][33] Specially, cationic polysaccharides (i.e., chitosan) have a high sensitivity to controlled degradation of C-O-C bond by hydrolysis as well as under high-dose radiation exposures. 26,34,35 Radiation induced C-O-C bond scission occurs more frequently among high molecular weight polymers and is described by homolysis or heterolysis mechanisms.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…8,29 Hydrolysis driven glycosidic bond (C-O-C) cleavage is well-known among carbohydrates and nucleic acids, rendering them an excellent drug-payload carrier in biological environments. [29][30][31][32][33] Specially, cationic polysaccharides (i.e., chitosan) have a high sensitivity to controlled degradation of C-O-C bond by hydrolysis as well as under high-dose radiation exposures. 26,34,35 Radiation induced C-O-C bond scission occurs more frequently among high molecular weight polymers and is described by homolysis or heterolysis mechanisms.…”
Section: Introductionmentioning
confidence: 99%
“…36,37 Additionally, homolytic rupture occurs at low energy as well as in the accidental radiation exposure range (1-6 Gy), favoring controlled drug release from radioprotective polymeric matrices. 33,35 A controlled and targeted cleavage of C-O-C bond upon radiation, while maintaining the material properties (i.e., biological activity) of the polymer would be a hallmark in designing a stimuli-responsive drug delivery system.…”
Section: Introductionmentioning
confidence: 99%