Abstract
The tryptophan (Trp) is an essential α-amino acid for humans and a bionic precursor for the neurotransmitter serotonin, which is known as “happiness hormone”. Simultaneous thermogravimetry and differential scanning calorimetry coupled with FTIR in air and N2 atmospheres, X-ray powder diffractometry, and infrared spectroscopy were used to characterize and to study the thermal behavior of Trp. The use of density functional theory was performed in order to propose the structure of Trp. The results provided information on the conformation form, thermal behavior, and thermal decomposition mechanism. The analysis permitted to suggest a new proposal of the mechanism of thermal decomposition of the Trp. The Kinect data indicated a relationship of the temperature and atmosphere in the reactions occurred in the Trp during heating.
Similar content being viewed by others
References
Katayama S, Mine Y. Antioxidative activity of amino acids on tissue oxidative stress in human intestinal epithelial cell model. J Agric Food Chem. 2007; doi:10.1021/jf070866p.
Yu M, Price J, Jensen P, Lovitt C. Copper, nickel, and zinc cyclam–amino acid and cyclam–peptide complexes may be synthesized with “click” chemistry and are noncytotoxic. Inorg Chem. 2011; doi:10.1021/ic2020012.
Patron L, Marinescu G, Culita D, Diamandescu L, Carp O. Thermal stability of amino acid-(tyrosine and tryptophan) coated magnetites. J Therm Anal Calorim. 2008; doi:10.1007/s10973-006-8082-4.
Vandyshev V, Ledenkov S. Acid-base and complexation properties of α-L-alanin in water-formamide mixtures. Russ J Phys Chem A. 2009; doi:10.1134/S0036024409120310.
Carvalho MA, De Paiva REF, Bergamini FRG, Gomes AF, Gozzo FC, Lustri WR, et al. A silver complex with tryptophan: Synthesis, structural characterization, DFT studies and antibacterial and antitumor assays in vitro. J Mol Struct. 2013; doi:10.1016/j.molstruc.2012.07.044.
Shen DK, Gu S. The mechanism for thermal decomposition of cellulose and its main products. Bioresour Technol. 2009; doi:10.1016/j.biortech.2009.06.095.
Görbitz CH, Törnroos KW, Day GM. Single-crystal investigation of l-tryptophan with Z’ = 16. Acta Crystallogr B. 2012; doi:10.1107/S0108768112033484.
Kalinowska M, Świsłocka R, Lewandowski W. The spectroscopic (FT-IR, FT-Raman, UV and 1 H, 13 C NMR) and theoretical studies of alkali metal o-methoxybenzoates. J Mol Struct. 2006; doi:10.1016/j.molstruc.2005.10.062.
Karabacak M, Mehmet C, Kurt M. An experimental and theoretical study of molecular structure and vibrational spectra of 2-chloronicotinic acid by density functional theory and ab initio Hartree–Fock calculations. J Mol Struct. 2008; doi:10.1016/j.molstruc.2007.10.004.
de Siqueira A, da Silva L. Caracterização Térmica e Espectroscópica de Piridin-2-ilaminometileno derivados dos Ácidos de Meldrum. Braz J Therm Anal. 2014; doi:10.1234/bjta.v3i1-2.17.
Vyazovkin S. Computational aspects of kinetic analysis: part C. The ICTAC Kinetics Project—the light at the end of the tunnel? Thermochim Acta. 2000; doi:10.1016/S0040-6031(00)00445-7.
Brown M, Maciejewski M, Vyazovkin S. Computational aspects of kinetic analysis: part A: the ICTAC kinetics project-data, methods and results. Thermochim Acta. 2000; doi:10.1016/S0040-6031(00)00443-3.
Vyazovkin S. A unified approach to kinetic processing of nonisothermal data. Int J Chem Kinet. 1996; doi:10.1002/(SICI)1097.
Lee C, Yang W, Parr R. Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988; doi:10.1103/PhysRevB.37.785.
Carvalho CT De, Siqueira a. B, Ionashiro EY, Pivatto M, Ionashiro M. Synthesis and characterization of solid 2-methoxycinnamylidenepyruvic acid. Eclet. Quim. 2008; 33:61–8. http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-46702008000400008&lng=en&nrm=iso&tlng=en.
Schlegel HB. Optimization of equilibrium geometries and transition structures. J Comput Chem. 1982; doi:10.1002/jcc.540030212.
Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993; doi:10.1063/1.464913.
Priakumari RO, Sheba SGS, Gunasekaran M. Synthesis, growth and characterization of non-linear optical material: l-Tryptophan p-nitrophenol (LTPNP) single crystal. Int J Light Electron Opt. 2014; doi:10.1016/j.ijleo.2014.04.095.
Wagner C, Baran E. Spectroscopic and magnetic behaviour of the copper (II) complex of L-tryptophan. Acta Farm. Bonaer. 2004;23(3):339–42.
Acknowledgements
The authors thank Company Mettler Toledo, LATIG (Laboratório de Análise Térmica Ivo Giolito) IQ-UNESP, FAPEMAT (Proc. 2013/09022-7), CNPq and the CAPES Foundations for financial support and computational facilities of Professor Sebastião Claudino da Silva-UFMT.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
da S. Mello, G., de P. Cardoso, A., Oliveira, E.W.R.S. et al. Tryptophan. J Therm Anal Calorim 122, 1395–1401 (2015). https://doi.org/10.1007/s10973-015-4916-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-015-4916-2