The Thermal Polycondensation of Glycine in the Presence of Urea

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After the discovery of the polycondensation of glycine to form the glycine oligomer by heating in the presence of urea in a sealed tube, we investigated in order to establish the optimum reaction conditions as well as to study the reaction mechanism. The optimum conditions are attained when a mixture of 0.0133 mol (1 g) of glycine and 0.0016 mol (0.1 g) of urea is heated at about 160 °C for 20–30 hr. Under these conditions, an oligomer, composed of glycine units, with a polymerization degree of 17–18 is obtained with a 50–52% yield. The mechanism of oligomer formation is considered to be as follows: first, the urea is melted and part of it is used for converting the glycine to the corresponding amide. The glycinamide thus formed and the glycine dissolve locally in the molten urea, resulting in condensation between them. A repetition of the condensation leads to longer peptide chains.
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