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Lithium hexamethyldisilazide initiated superfast ring opening polymerization of alpha-amino acid N-carboxyanhydrides

Author

Listed:
  • Yueming Wu

    (East China University of Science and Technology)

  • Danfeng Zhang

    (East China University of Science and Technology)

  • Pengcheng Ma

    (East China University of Science and Technology)

  • Ruiyi Zhou

    (East China University of Science and Technology)

  • Lei Hua

    (East China University of Science and Technology)

  • Runhui Liu

    (East China University of Science and Technology)

Abstract

Polypeptides have broad applications and can be prepared via ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCAs). Conventional initiators, such as primary amines, give slow NCA polymerization, which requires multiple days to reach completion and can result in substantial side reactions, especially for very reactive NCAs. Moreover, current NCA polymerizations are very sensitive to moisture and must typically be conducted in a glove box. Here we show that lithium hexamethyldisilazide (LiHMDS) initiates an extremely rapid NCA polymerization process that is completed within minutes or hours and can be conducted in an open vessel. Polypeptides with variable chain length (DP = 20–1294) and narrow molecular weight distribution (Mw/Mn = 1.08–1.28) were readily prepared with this approach. Mechanistic studies support an anionic ring opening polymerization mechanism. This living NCA polymerization method allowed rapid synthesis of polypeptide libraries for high-throughput functional screening.

Suggested Citation

  • Yueming Wu & Danfeng Zhang & Pengcheng Ma & Ruiyi Zhou & Lei Hua & Runhui Liu, 2018. "Lithium hexamethyldisilazide initiated superfast ring opening polymerization of alpha-amino acid N-carboxyanhydrides," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-07711-y
    DOI: 10.1038/s41467-018-07711-y
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    Cited by:

    1. Tianyu Wu & Min Zhou & Jingcheng Zou & Qi Chen & Feng Qian & Jürgen Kurths & Runhui Liu & Yang Tang, 2024. "AI-guided few-shot inverse design of HDP-mimicking polymers against drug-resistant bacteria," Nature Communications, Nature, vol. 15(1), pages 1-22, December.
    2. Jiayang Xie & Min Zhou & Yuxin Qian & Zihao Cong & Sheng Chen & Wenjing Zhang & Weinan Jiang & Chengzhi Dai & Ning Shao & Zhemin Ji & Jingcheng Zou & Ximian Xiao & Longqiang Liu & Minzhang Chen & Jin , 2021. "Addressing MRSA infection and antibacterial resistance with peptoid polymers," Nature Communications, Nature, vol. 12(1), pages 1-13, December.
    3. Ying Liu & Zhongwu Ren & Nannan Zhang & Xiaoxin Yang & Qihua Wu & Zehong Cheng & Hang Xing & Yugang Bai, 2023. "A nanoscale MOF-based heterogeneous catalytic system for the polymerization of N-carboxyanhydrides enables direct routes toward both polypeptides and related hybrid materials," Nature Communications, Nature, vol. 14(1), pages 1-12, December.

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