First Aldehyde-Functionalized Poly(2-oxazoline)s for Chemoselective Ligation

Authors

  • Christian Taubmann,

    1. Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany
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  • Robert Luxenhofer,

    1. Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany
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  • Sonia Cesana,

    1. Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany
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  • Rainer Jordan

    Corresponding author
    1. Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany
    2. Department of Chemistry, Chemical Engineering and Materials Science, Polytechnic University, Six Metrotech Center, Brooklyn, New York 11201, U.S.A.
    • Lehrstuhl für Makromolekulare Stoffe, Department Chemie, Technische Universität München, Lichtenbergstraße 4, 85747 Garching, Germany. Fax: +49 89 289 13562
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Abstract

Summary: A protected aldehyde-functionalized 2-oxazoline, 2-[3-(1,3)-dioxolan-2-ylpropyl]-2-oxazoline (DPOx), was synthesized from commercially available compounds in high yields. The polymerization of DPOx with different initiators proceeds via a living ionic mechanism; thus, the polymers were of low polydispersity and the degree of polymerization could be precisely adjusted. Copolymerization with 2-methyl-2-oxazoline gave water-soluble statistical copolymers. Hydrolysis of the homo- and copolymers resulted in well-defined, aldehyde-bearing poly(2-oxazoline)s. The aldehyde side functions reacted quantitatively with an amino-oxy compound to form the corresponding oxime.

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