Open-vessel Synthesis of Poly-N-methoxyethylglycine

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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