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Issue 3, 2012
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Amino acid vinyl esters: a new monomer palette for degradable polycationic materials

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Abstract

Toward the goal of developing degradable polycationic materials with tunable backbone charge densities and hydrophilicities, we report the optimized syntheses and polymerization activities of a series of N-Boc-protected amino acidO-vinyl ester (BAAVE) monomers derived from Boc-protected glycine, alanine, valine, and proline. The homopolymerization and copolymerization behaviors of these monomers under thermally initiated conventional free radical polymerization conditions are studied. By conducting copolymerizations of (N-tert-butoxycarbonyl)glycine vinyl ester (BGVE) with vinyl acetate (VAc) at various feed ratios and by analyzing the compositions of the resulting polymers produced at 88 °C using 1,1′-azobis(cyclohexane-1-carbonitrile) (V-40) initiation, we find that the reactivity ratios are rBGVE = 1.61 ± 0.12 and rVAc = 0.82 ± 0.07. Treatment of poly(VAc-co-BAAVE) with neat CF3COOH selectively unmasks the Boc-protected amine functionalities to furnish cationic poly(VAc-co-AAVE·CF3COOH) copolymers. Alternatively, treatment of these random copolymers with methanolic HCl results in the complete hydrolysis of both the Boc-protecting groups as well as the acetate esters, enabling access to well-defined, hydrophilic, polycationic amino acid ester-functionalized poly(vinyl alcohol) materials.

Graphical abstract: Amino acid vinyl esters: a new monomer palette for degradable polycationic materials

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Publication details

The article was received on 08 Nov 2011, accepted on 30 Dec 2011 and first published on 20 Jan 2012


Article type: Paper
DOI: 10.1039/C2PY00531J
Citation: Polym. Chem., 2012,3, 741-750
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    Amino acid vinyl esters: a new monomer palette for degradable polycationic materials

    G. B. Thomas, C. E. Lipscomb and M. K. Mahanthappa, Polym. Chem., 2012, 3, 741
    DOI: 10.1039/C2PY00531J

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