CRCU

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (1): 153-158.doi: 10.1007/s40242-024-3260-0

• Articles • Previous Articles    

Open-vessel Synthesis of Poly-N-methoxyethylglycine

LIU Guojian1,2, MA Ke1,2, CHEN Qi1,2, ZHANG Donghui1,3, LIU Runhui1,2   

  1. 1. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China;
    2. Key Laboratory for Ultrafine Materials of Ministry of Education, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism, Research Center for Biomedical Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China;
    3. School of Biotechnology, East China University of Science and Technology, Shanghai 200237, P. R. China
  • Received:2023-11-24 Online:2024-02-01 Published:2024-01-24
  • Contact: ZHANG Donghui, LIU Runhui E-mail:zhangdonghui@ecust.edu.cn;rliu@ecust.edu.cn
  • Supported by:
    This work was supported by the National Key Research and Development Program of China (No. 2022YFC2303100), the National Natural Science Foundation of China (Nos. 22075078, 22205063), the Shanghai Sailing Program, China (No. 22YF1410100) and the Fund of the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission), China.

Abstract: Polypeptoids are widely used in biological applications owing to their diverse functions and proteolytic stability. One type of polypeptoids, poly-N-methoxyethylglycine (P-Nmeg), has been found to possess remarkable hydrophilicity and notable properties in terms of protein, cell, and bacterial antifouling. However, the currently known synthesis methods of P-Nmeg include solid-phase synthesis, which is time-consuming and difficult to scale up, and N-substituted N-carboxyanhydride (NNCA) ring-opening polymerization, whose monomers were difficult to store. In this study, we used the chemical stable Nmeg N-phenoxycarbonyl (NPC) as the monomer, which was obtained without the use of highly toxic reactants, such as phosgene or phosphorus halide, to synthesize P-Nmeg under open-vessel conditions. By adding BnNH2 as an initiator at 80℃, we can obtain controllable short chain length P-Nmeg with narrow dispersity.

Key words: Open-vessel, Polypeptoid synthesis, Poly-N-methoxyethylglycine, Stable monomer, Narrow dispersity