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    General Route toward Side-Chain-Functionalized α-Helical Polypeptides
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    Department of Chemistry and Macromolecular Studies Group, Louisiana State University, Baton Rouge, Louisiana 70803
    * To whom correspondence should be addressed. E-mail: [email protected]
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    Biomacromolecules

    Cite this: Biomacromolecules 2010, 11, 6, 1585–1592
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    https://doi.org/10.1021/bm1002174
    Published May 13, 2010
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    Abstract

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    A series of poly(γ-chloropropyl-l-glutamate) (PCPLG) with controlled polymer molecular weight (MW = 5−28 kg·mol−1) and molecular weight distribution (PDI = 1.16−1.26) have been prepared from hexamethyldisilazane (HMDS)-mediated ring-opening polymerization (ROP) of γ-chloropropyl-l-glutamic acid based N-carboxylanhydride (CP-NCA). CD, FTIR, and WAXS analysis reveal that the polymers adopt α-helical conformations both in solution and the solid state. Their helical surfaces can be readily decorated with functional moieties to confer desired properties, as demonstrated by the quantitative derivatization of the PCPLG side chains with azido functional groups that are amendable to “click” chemistry. Subsequent side-chain conjugation with mannose moieties via copper-mediated [2 + 3] alkyne−azide 1,3-dipolar cycloaddition affords water-soluble mannose−polypeptide conjugates with quantitative grafting efficiency occurring under mild conditions. CD analysis reveals that the mannose−polypeptide conjugates also retain α-helical conformations in aqueous solution.

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    FTIR and ESI MS spectra of 3 (Figures S1 and S2), SEC traces of the PCPLG prepared from polymerizations of 3 with different monomer-to-initiator ratios (Figure S3), a representative temporal evolution of the FTIR spectrum of HMDS-mediated ROP of 3 (Figure S4) and the corresponding kinetic data analysis using the first-order kinetic rate law (Figure S5), TGA and DSC traces of PCPLG (Figure S6-A, B) and the tabulated results (Table S1), 1H NMR spectra of PCPLG, PAPLG in CDCl3/CF3CO2D (v/v = 85:15) and PPLG-g-mannose in D2O/CF3CO2D (v/v = 85:15; Figure S7), 13C{1H} NMR spectra of PCPLG, PAPLG in CDCl3, and PPLG-g-mannose in D2O (Figure S8), SEC traces of PPLG-g-mannose and its respective PCPLG and PAPLG precursors (Figure S9), SAXS diffractograms of PCPLG, PAPLG, and PPLG-g-mannose (Figure S10), and POM images of PCPLG solid at 20 and 150 °C (Figure S11). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Biomacromolecules 2010, 11, 6, 1585–1592
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