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Revisiting Secondary Structures in NCA Polymerization: Influences on the Analysis of Protected Polylysines

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Macromolecules 2014, 47, 3, 928-936
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    Revisiting Secondary Structures in NCA Polymerization: Influences on the Analysis of Protected Polylysines
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    † Institute of Organic Chemistry, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
    ‡ Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
    *E-mail: [email protected] (M.B.).
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    Macromolecules

    Cite this: Macromolecules 2014, 47, 3, 928–936
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    https://doi.org/10.1021/ma5000392
    Published January 22, 2014
    Copyright © 2014 American Chemical Society
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    Abstract

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    Two series (degree of polymerization: 20–200) of polylysines with Z and TFA protecting groups were synthesized, and their behavior in a range of analytical methods was investigated. Gel permeation chromatography of the smaller polypeptides reveals a bimodal distribution, which is lost in larger polymers. With the help of GPC, NMR, circular dichroism (CD), and MALDI-TOF, it was demonstrated that the bimodal distribution is not due to terminated chains or other side reactions. Our results indicate that the bimodality is caused by a change in secondary structure of the growing peptide chain that occurs around a degree of polymerization of about 15. This change in secondary structure interferes strongly with the most used analysis method for polymers—GPC—by producing a bimodal distribution as an artifact. After deprotection, the polypeptides were found to exhibit exclusively random coil conformation, and thus a monomodal GPC elugram was obtained. The effect can be explained by a 1.6-fold increase in the hydrodynamic volume at the coil–helix transition. This work demostrates that secondary structures need to be carefully considered when performing standard analysis on polypeptidic systems.

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    Supporting Information

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    GPC, CD, and NMR and experimental data of PLys(TFA), additional MALDI-TOF spectra, an NMR spectrum in HFIP, DOSY spectrum, GPC traces at different time points of the polymerization, and corrected molecular weights of PLys(Z) as well as equations for the Rh estimations. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Macromolecules 2014, 47, 3, 928–936
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    https://doi.org/10.1021/ma5000392
    Published January 22, 2014
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