Master of Science
Department of Chemistry
Murray, Stephen, Studies in isotopic labelling of amino acids and polypeptides, Master of Science thesis, Department of Chemistry, University of Wollongong, 1973. http://ro.uow.edu.au/theses/2629
The aromatic protone of amino acids and samll peptides have been exchanged with deuterium under conditions which produced no significant exchange of the non - aromatic protons. A heterogeneous catalyst syrstem was found to be suitable for the deuterium exchange of biologically active molecules, and platinum used in a 1:1 molar ratio with the labelled compound, was the most selective of the G-roup VIII metal catalysts. Substantial exchange of the aromatic protons of phenylalanine, tyrosine, tryptophan and histidine occurred when the reaction was allowed to proceed for 1 day, at 70°C. A similar deuterium distribution was found in the aromatic amino acid residues of a number of model peptides under the same reaction conditions. Substantial incorporation into the diketopiperazine ring of labelled cyclo - dipeptides was fou,nd when iridium, was used to catalyse the reaction. The optical purity and any peptide bonds present in the labelled compounds were preserved through out the exchange reactions.