The reaction of tryptophan with cystine during acid hydrolysis of proteins. Formation of tryptathionine as a transient intermediate in a model system.
Under the conditions commonly used to hydrolyze proteins with 6 M HCl, tryptophan reacted with cystine to give a transient intermediate, which was isolated and identified as 2-(2-amino-2-carboxyethylthio)tryptophan (tryptathionine) by NMR studies, etc. Studies on the formation and degradation of the above compound showed that beta-3-oxoindolylalanine and cysteine, which were previously reported to be the main degradation products of tryptophan and cystine, respectively, are formed by the hydrolysis of this intermediate during the course of the reaction.
D000596:Amino Acids / Q000032:analysis; D003553:Cystine; D004151:Dipeptides; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D011506:Proteins; D014364:Tryptophan
D000596:Amino Acids; D004151:Dipeptides; D011506:Proteins; D003553:Cystine; D014364:Tryptophan