Open-vessel Synthesis of Poly-N-methoxyethylglycine

Guojian Liu, Ke Ma, Qi Chen, Donghui Zhang, Runhui Liu

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (1) : 153-158. DOI: 10.1007/s40242-024-3260-0
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Open-vessel Synthesis of Poly-N-methoxyethylglycine

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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 °C, we can obtain controllable short chain length P-Nmeg with narrow dispersity.

Keywords

Open-vessel / Polypeptoid synthesis / Poly-N-methoxyethylglycine / Stable monomer / Narrow dispersity

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Guojian Liu, Ke Ma, Qi Chen, Donghui Zhang, Runhui Liu. Open-vessel Synthesis of Poly-N-methoxyethylglycine. Chemical Research in Chinese Universities, 2024, 40(1): 153‒158 https://doi.org/10.1007/s40242-024-3260-0

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