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Facile Synthesis of High Molecular Weight Polypeptides via Fast and Moisture Insensitive Polymerization of α-Amino Acid N-Carboxyanhydrides

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Abstract

Polypeptides have been widely utilized in the fields of biomaterials and biomedicine. Ever since N-carboxyanhydride (NCA) was reported by Hermann Leuchs in 1906, ring-opening polymerization of NCAs has been extensively used to prepare polypeptides. Despite continuous innovations, it is still challenging to synthesize polypeptides in high molecular weight efficiently. To address this challenge, we developed KHMDS/NaHMDS initiated fast NCA polymerization that is also moisture tolerant, open-flask amenable and terminal tunable. This NCA polymerization was able to proceed in most common solvents and meet the solubility requirement of variable NCA monomers and corresponding polypeptides. KHMDS can initiate γ-benzyl-L-glutamate-N-carboxyanhydride (BLG NCA) polymerization in a reaction rate 92 times faster than does hexylamine and 80 times faster than does triethylamine. This NCA polymerization also demonstrated easy and fast synthesis of gram-scale long chain polypeptides in an open flask.

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 21774031 and 21861162010), the National Key Research and Development Program of China (No. 2016YFC1100401), Research Program of State Key Laboratory of Bioreactor Engineering, State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Donghua University, the Fundamental Research Funds for the Central Universities (Nos. 22221818014 and 50321041917001). The authors also thank Research Center of Analysis and Test of East China University of Science and Technology for the help on the characterization.

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  1. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200237, China

    Yue-Ming Wu, Wei-Wei Zhang, Rui-Yi Zhou, Qi Chen, Chen-Yu Xie & Run-Hui Liu

  2. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, China

    Heng-Xue Xiang, Bin Sun & Mei-Fang Zhu

  3. Key Laboratory of Specially Functional Polymeric Materials and Related Technology (ECUST) Ministry of Education, Key Laboratory for Ultrafine Materials of Ministry of Education, Research Center for Biomedical Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai, 200237, China

    Wei-Wei Zhang, Rui-Yi Zhou, Qi Chen, Chen-Yu Xie & Run-Hui Liu

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Facile Synthesis of High Molecular Weight Polypeptides via Fast and Moisture Insensitive Polymerization of α-Amino Acid N-Carboxyanhydrides

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Wu, YM., Zhang, WW., Zhou, RY. et al. Facile Synthesis of High Molecular Weight Polypeptides via Fast and Moisture Insensitive Polymerization of α-Amino Acid N-Carboxyanhydrides. Chin J Polym Sci 38, 1131–1140 (2020). https://doi.org/10.1007/s10118-020-2471-1

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