A. Justino, A. C. S. Carvalho, L. G. de Vasconcelos
2021
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Journal
Journal of Thermal Analysis and Calorimetry
Abstract
Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data.