Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 52, Issue 51, Pages 13699-13702Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201306391
Keywords
carbohydrates; pH-responsive; poly(orthoester); polymerization; tetra-n-butylammonium iodide
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Funding
- Central Michigan University [C61661]
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pH-Responsive polymers have great potential in biomedical applications, including the selective delivery of preloaded drugs to tissues with low pHvalues. These polymers usually contain acid-labile linkages such as esters and acetals/ketals. However, these linkages are only mildly pH-responsive with relatively long half-lives (t(1/2)). Orthoester linkages are more acid-labile, but current methods suffer from synthetic challenges and are limited to the availability of monomers. To address these limitations, a sugar poly(orthoester) was synthesized as a highly pH-responsive polymer. The synthesis was achieved by using 2,3,4-tri-O-acetyl--D-glucopyranosyl bromide as a difunctional AB monomer and tetra-n-butylammonium iodide (TBAI) as an effective promoter. Under optimal conditions, polymers with molecular weights of 6.9kDa were synthesized in a polycondensation manner. The synthesized glucose poly(orthoester), wherein all sugar units were connected through orthoester linkages, was highly pH-responsive with a half-life of 0.9, 0.6, and 0.2hours at pH6, 5, and 4, respectively.
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