Thermoresponsive Oligo(ethylene glycol) Functionalized Poly‑L‑cysteine Thermoresponsive Oligo(ethylene glycol) Functionalized Poly‑L‑cysteine

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Thermoresponsive Oligo(ethylene glycol) Functionalized Poly‑L‑cysteine

Xiaohui Fu, Yong Shen, Wenxin Fu, and Zhibo Li*

Macromolecules 2013, 46, 3753−3760

A series of new functional amino acids were prepared in high yield via thiol-ene Michael addition between cysteine and monomethoxy oligo(ethylene glycol) (OEG) functionalized methacrylates (OEGxMA) and acrylate (OEGxA). These OEGylated cysteine derivatives were converted into polymerizable N-carboxyanhydride (NCA) monomers using triphosgene. Subsequent ring opening polymerization (ROP) of these NCA monomers gave a series of OEGylated polycysteine (poly-EGxMA-C or poly-EGxA-C) homopolypeptides. Depending on the chain length of OEG, poly-EGxMA-C or poly-EGxA-C polypeptides displayed different solubility and secondary structure in water. More importantly, the obtained polypeptides can display reversible thermal responsive properties in water when the x value is between 3 and 5. The synthetic strategy represents a new highly efficient method to prepare nonionic functional polypeptides with tunable physical properties.