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Analogues of Poly(l‑phosphoserine) via Living Polymerization of Phosphonate-Containing N‑Carboxyanhydride Monomers

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We have synthesized new phosphonate-containing α-amino acid N-carboxyanhydride (NCA) monomers and used these to prepare well-defined phosphonate-containing polypeptides and block copolypeptides. These NCAs were found to undergo living polymerization to high molecular weights with narrow chain length distributions. The methods described here demonstrate that phosphono polypeptides are also readily incorporated into block copolymers with controlled architecture and composition. One polymer, poly(l-phosphonohomoalanine) (poly(Pha)), is an isosteric analogue of poly(l-phosphoserine) and was found to display a pH-responsive conformational change. The pH-responsive α-helical conformation of poly(Pha) is unprecedented and may prove to be useful in the preparation of stimuli-responsive block copolypeptides containing poly(Pha) segments.

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