Synthesis of end-functionalized phosphate and phosphonate-polypeptides by ring-opening polymerization of their corresponding N-carboxyanhydride

Literature Information

Publication Date 2013-05-07
DOI 10.1039/C3PY00409K
Impact Factor 5.582
Authors

Soumen Das, Mrityunjoy Kar, Sayam Sen Gupta


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Abstract

Phosphopolypeptides provide an interesting biomimetic analog for phosphorylated proteins that are involved in biomineralization. We have developed a high yielding synthesis of cysteine-based phosphate and phosphonate N-carboxyanhydride (NCA) by using the thiol–ene coupling reaction. These phosphate and phosphonate NCA monomers underwent polymerization using simple primary amine initiators to form well defined homophosphopolypeptides. Using a bifunctional initiator we were able to install a “clickable” alkyne or azide group at the end of the polypeptide chain. We were also able to successfully synthesize fully water-soluble phosphonate based polypeptides by hydrolysis of the corresponding phosphonate ester groups in the polypeptide. These water-soluble phosphopolypeptides adopt a random coil conformation at physiological pH.

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Polymer Chemistry

Polymer Chemistry
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