Polymerization of Glycine and  L–Phenylalanine to Short Homooligopeptides  by Nitrobiuret Under Aqueous Conditions

Arthur O. Hawtrey; Mario Ariatti; Johann M. Van ZYL

Volume : II, Issue : VI, June - 2013

Polymerization of Glycine and L–Phenylalanine to Short Homooligopeptides by Nitrobiuret Under Aqueous Conditions

Arthur O. Hawtrey, Mario Ariatti, Johann M. Van Zyl

Abstract :

The reactions between nitrobiuret and the amino acids glycine and L-phenylalanine at pH 10, have been examined by mass spectrometry. Initially, the expected amino acyl biurets are formed, however these may react with a further nitrobiuret molecule yielding the amino acyl biuret N-carboxyanhydride. The anhydride then N-acylates a second amino acid molecule to afford a dipeptide derivative. The process is repeated and peptides up to glycine5, glycine5-biuret, phenylalanine4 and phenylalanine5-biuret have been detected. In addition the unstable N-carboxyanhydrides may also be converted to their respective ureides with loss of CO2. These reactions are of particular interest to the area of pre-biotic chemistry.