Solid state stability studies of model dipeptides: aspartame and aspartylphenylalanine

Journal of Pharmaceutical Sciences
S S Leung, D J Grant

Abstract

Some solid-state pharmaceutical properties and the solid-state thermal stability of the model dipeptides aspartame (APM) and aspartylphenylalanine (AP), have been investigated. Studies by differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), high-performance liquid chromatography, powder X-ray diffraction, and optical microscopy have shown that the dipeptides undergo solid state intramolecular aminolysis of the type, solid --> solid + gas. This reaction was observed for APM at 167-180 degrees C with the liberation of methanol and for AP at 186-202 degrees C with the liberation of water. The exclusive solid product of the degradation reaction of both dipeptides is the cyclic compound 3-(carboxymethyl)-6-benzyl-2,5-dioxopiperazine. The rates of the degradation reactions were monitored by isothermal TGA and by temperature-ramp DSC and were found to follow kinetics based on nucleation control with activation energies of about 266 kJ mol(-1) for APM and 234 kJ mol(-1) for AP.

References

Feb 1, 1992·International Journal of Peptide and Protein Research·C H Görbitz, M C Etter
Jul 1, 1991·International Journal of Peptide and Protein Research·Y K Kang

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Citations

Apr 28, 2001·Advanced Drug Delivery Reviews·S R VippaguntaD J Grant
Nov 5, 1999·International Journal of Pharmaceutics·M E Brown, B D Glass
Nov 17, 1999·Journal of Pharmaceutical Sciences·T Hamaura, J M Newton
May 7, 1999·Journal of Pharmaceutical Sciences·M C Lai, E M Topp
Apr 21, 1998·Journal of Pharmaceutical Sciences·S S LeungD J Grant
Apr 21, 1998·Journal of Pharmaceutical Sciences·S S LeungD J Grant
Mar 16, 2012·Journal of Pharmaceutical Sciences·Zhixin ZongLee E Kirsch
Feb 2, 2008·Journal of Pharmaceutical Sciences·Suman A LuthraMarcel Utz
Jul 13, 2002·Journal of Pharmaceutical Sciences·Zedong DongDavid J W Grant
Jan 30, 2010·Journal of Pharmaceutical Sciences·Biren K JoshiScott L Sides
Apr 26, 2014·Critical Reviews in Food Science and Nutrition·Shan-Yang Lin, Chih-Cheng Lin
Dec 8, 2014·Advanced Drug Delivery Reviews·Olivier Mozziconacci, Christian Schöneich
Feb 9, 2000·Journal of Pharmaceutical Sciences·Y GuoG Zografi
Jul 19, 2019·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marat A ZiganshinValery V Gorbatchuk
Mar 10, 2017·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Youngsun LeeHoonjeong Kwon
Jul 17, 1999·Analytical Chemistry·C K LariveS Bogdanowich-Knipp

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