Shuhei Yamada, M. Goto, T. Endo
Jun 14, 2016
Citations
1
Influential Citations
8
Citations
Journal
Polymer
Abstract
Abstract Polypeptides bearing a reactive alkene moiety, including poly- dl -allylglycine ( PGly(allyl) ) and poly- dl -pentenylglycine ( PGly(pent) ) have been prepared through the polycondensation of activated urethane derivatives, N -phenoxycarbonyl derivative of α-amino acids. These urethane derivatives of dl -allylglycine ( NPC-Gly(allyl) ) and dl -pentenylglycine ( NPC-Gly(pent) ), are prepared by the N -carbamylation of the onium salt of the corresponding α-amino acid with diphenyl carbonate. The polycondensation of urethane derivatives proceeds when heated at 60 °C in N , N -dimethylacetamide, using amines as initiators, along with the elimination of phenol and CO 2 , to give the corresponding polypeptides without any degradation of alkene moieties. Varying the feed ratio of the urethane derivative to the initiator gives a predictable molecular weight with a narrow polydispersity index. Post-polymerization modifications of the alkene moiety of polypeptide are achieved with a high efficiency through a typical radical thiol-ene addition using a range of thiol-containing compounds, indicating the broad scope of this method as a conjugation tool for functional molecules.