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
View Original
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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Source Journal
Polymer Chemistry
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