Abstract
N-Cyanoethylglycine was synthesized from glycine and acrylonitrile, and converted into its N-carboxyanhydride (NCA) by Leuch’s method. The NCA was polymerized in a HCONMe2 solution using an amine as the initiator to give, for the first time, a white, powderic, amorphous polymer having Pn=15–16. The rate of polymerization was much smaller than that of N-n-butylglycine NCA under the same conditions, and the low basicity of the amino group at the growing end, which is a result of an electron-withdrawing effect of cyanoethyl group, was found to be responsible for the slow polymerization. Poly(N-cyanoethylglycine) is soluble in aprotic solvents such as HCONMe2, Me2SO, and Me2CO, and its main-chain peptide bonds comprise ca. 70% of cis form and ca. 30% of trans form in Me2SO. Poly(N-cyanoethylglycine) is therefore flexible and compact in organic solvents. A part of the side chains of poly(N-cyanoethylglycine) was reduced into 3-aminopropyl groups by the hydro genation.
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Imanishi, Y., Tsuchida, T. & Higashimura, T. Synthesis and Characterization of Poly(N-cyanoethylglycine). Polym J 10, 287–292 (1978). https://doi.org/10.1295/polymj.10.287
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DOI: https://doi.org/10.1295/polymj.10.287