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Easy synthesis and ring-opening polymerization of 5-Z-amino-δ-valerolactone: New degradable amino-functionalized (Co)polyesters

Authors

  • Sebastien Blanquer,

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Julien Tailhades,

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Vincent Darcos,

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Muriel Amblard,

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Jean Martinez,

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Benjamin Nottelet,

    Corresponding author
    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
    • Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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  • Jean Coudane

    1. Max Mousseron Institute of Biomolecules (IBMM), UMR CNRS 5247, University of Montpellier 1, University Montpellier 2, Faculty of Pharmacy, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France
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Abstract

Novel 5-Z-amino-δ-valerolactone (5-NHZ-VL) was synthesized with an aim to prepare degradable polyesters and copolyesters having amino pendant groups. Following a straightforward and efficient synthetic pathway, 5-NHZ-VL was obtained in only two steps and up to 50% yield. The monomer was fully characterized by 1H NMR, 13C NMR, ESI mass spectrometry, and HPLC. Various conventional conditions were tested for this lactone ring-opening polymerization and led to the novel corresponding poly(5-NHZ-VL) (Mn = 7000 g/mol; PD = 1.2). Following this homopolymerization, 5-NHZ-VL was copolymerized with ε-caprolactone to generate a family of copolyesters with an amino-group content ranging from 10 to 80%. Finally, the polyelectrolyte poly(5-NH3+-VL) was recovered by removal of the protecting group under acidic conditions, and integrity of the polyester backbone was confirmed by 1H NMR. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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