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Non-isocyanate urethane linkage formation using l-lysine residues as amine sources

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Abstract

Bio-based polyurethane materials are broadly applied in medicine as drug delivery systems. Nevertheless, their synthesis comprises the use of petroleum-based toxic amines, isocyanates and polyols, and their biocompatibility or functionalization is limited. Therefore, the use of lysine residues as amine sources to create non-isocyanate urethane (NIU) linkages was investigated. Therefore, a five-membered biscyclic carbonate (BCC) was firstly synthetized and reacted with a protected lysine, a tripeptide and a heptapeptide to confirm the urethane linkage formation with lysine moiety and to optimize reaction conditions. Afterwards, the reactions between BCC and a model protein, elastin-like protein (ELP), and β-Lactoglobulin (BLG) obtained from whey protein, respectively, were performed. The synthesized protein materials were structural, thermally and morphologically characterized to confirm the urethane linkage formation. The results demonstrate that using both simple and more complex source of amines (lysine), urethane linkages were effectively achieved. This pioneering approach opens the possibility of using proteins to develop non-isocyanate polyurethanes (NIPUs) with tailored properties.

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Acknowledgements

TSSIPRO—Technologies For Sustainable And Smart Innovative Products, NORTE-01-0145-FEDER-000015 and COMPETE 2020 Programme and National Funds through FCT—Portuguese Foundation for Science and Technology under the project UID/CTM/50025/2013. The authors would like to thank Professor Sílvia Lima and Professor Susana Costa from the Chemistry Department at the University of Minho for kindly allow the use of Microwave CEM Discover SPS equipment and for all knowledge shared during this work.

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Authors and Affiliations

  1. Institute of Polymers and Composites/I3N, University of Minho, Campus de Azurém, 4800-058, Guimarães, Portugal

    Cláudia Peixoto, Ana M. S. Soares, Andreia Araújo & Ana V. Machado

  2. Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA

    Bradley D. Olsen

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  1. Cláudia Peixoto
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  2. Ana M. S. Soares
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  3. Andreia Araújo
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  4. Bradley D. Olsen
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  5. Ana V. Machado
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Correspondence to Ana M. S. Soares.

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Peixoto, C., Soares, A.M.S., Araújo, A. et al. Non-isocyanate urethane linkage formation using l-lysine residues as amine sources. Amino Acids 51, 1323–1335 (2019). https://doi.org/10.1007/s00726-019-02770-x

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