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Tryptophan

A proposal of the mechanism of thermal decomposition

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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.

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References

  1. 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.

    Google Scholar 

  2. 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.

    Google Scholar 

  3. 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.

    Google Scholar 

  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.

    Google Scholar 

  5. 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.

    Google Scholar 

  6. 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.

    Google Scholar 

  7. Görbitz CH, Törnroos KW, Day GM. Single-crystal investigation of l-tryptophan with Z’ = 16. Acta Crystallogr B. 2012; doi:10.1107/S0108768112033484.

    Google Scholar 

  8. 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.

    Google Scholar 

  9. 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.

    Google Scholar 

  10. 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.

    Google Scholar 

  11. 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.

    Google Scholar 

  12. 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.

    Google Scholar 

  13. Vyazovkin S. A unified approach to kinetic processing of nonisothermal data. Int J Chem Kinet. 1996; doi:10.1002/(SICI)1097.

    Google Scholar 

  14. 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.

    Google Scholar 

  15. 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.

  16. Schlegel HB. Optimization of equilibrium geometries and transition structures. J Comput Chem. 1982; doi:10.1002/jcc.540030212.

    Google Scholar 

  17. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993; doi:10.1063/1.464913.

    Google Scholar 

  18. 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.

    Google Scholar 

  19. Wagner C, Baran E. Spectroscopic and magnetic behaviour of the copper (II) complex of L-tryptophan. Acta Farm. Bonaer. 2004;23(3):339–42.

    CAS  Google Scholar 

Download references

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.

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Correspondence to Adriano B. Siqueira.

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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

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  • DOI: https://doi.org/10.1007/s10973-015-4916-2

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