Synthesis of Peptides Histamine H2 Receptors in Solid-Phase Assisted by Microwave

Authors

  • Edgar A. Reynoso-Soto Instituto Tecnológico de Tijuana
  • Ignacio A. Rivero Instituto Tecnológico de Tijuana

DOI:

https://doi.org/10.29356/jmcs.v54i3.929

Keywords:

Solid Phase, Peptide, Microwave

Abstract

The synthesis of histamine H2 receptors peptides was conducted using the methodology of solid phase assisted by microwaves. Microwaves can reduce the reaction times during the coupling and deprotection steps to obtain the desired peptide sequence. The coupling reaction was carried out with a mixture of N,N′-diisopropylcarbodiimide (DIC) and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU). The purity and yield are improved in peptide synthesis assisted by microwaves. Coupling reactions and deprotection on Rink resin were carried out in 5 min depending on amino acid and the length of the peptide chain.

 

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Author Biographies

Edgar A. Reynoso-Soto, Instituto Tecnológico de Tijuana

Centro de Graduados e Investigación del Instituto Tecnológico de Tijuan

Ignacio A. Rivero, Instituto Tecnológico de Tijuana

Centro de Graduados e Investigación del Instituto Tecnológico de Tijuana

Instituto Nacional de Investigaciones Nucleares, Departamento de Química

References

1. (a) Barker, R. Organic Chemistry of Biological Compounds, Prentice-Hall, Englewood Cliffs, 1971. (b) Bladon, C. The Chemistry of Natural Products, Thomsom R. H. Ed, Blackie Academic and Professional (Chapman-Hall), Glasgow, 1993.
2. Rivero, I. A.; González, T.; Basterrechea, M. Rev. Soc. Quím. Méx. 2004, 48, 310-314.
3. (a) Merrifield, R. B.; Mitchell, A. R.; Clarke, J. E. J. Org. Chem. 1974, 39, 660–668. (b) Yu, H. M.; Chen, S. T.; Wang, K. J. Org. Chem. 1992, 57, 4781–4784.
4. (a) Stadler, A.; Kappe, C. O. Eur. J. Org. Chem. 2001, 919–925. (b) Stadler, A.; Kappe, C. O. Tetrahedron 2001, 57, 3915–3920. (c) Leadbeater, N. E.; Torenius, H. M. J. Org. Chem. 2002, 67, 3145–3148.
5. Soriano-Mora, J. M. Nuevos reactivos poliméricos para el acoplamiento y protección de aminoácidos, Tesis doctoral, Facultad de Ciencias, Universidad de Alicante, 2002, p19.
6. DeTar, D. F.; Silverstein, R. J. Am. Chem. Soc. 1966, 88, 1020-1023.
7. Arendt, A.; Kolodziejczyk, A. M. Tetrahedron Lett. 1978, 19, 3867-3868.
8. Scott, F. L.; Glick, R. E.; Winstein, S. Experientia 1957, 13, 183-185.
9. Albericio, F.; Chinchilla, R.; Dodsworth, D. J.; Nájera, C. Org. Prep. Proc. Int. 2001, 33, 203-304.
10. Bishnu, P. J.; Park, J. P.; Kim, J. M., Lohani, C. R.; Cho, H.; Lee, K. H. Tetrahedron Lett. 2008, 49, 98–101.
11. Black, J. W.; Duncan, W. A. M.; Durant, C. J.; Ganellin, C. R.: Parsons, E. M. Nature 1972, 236, 385-390
12. Durant, G. J.; Ganellin, C. R.; Parson, M. E. J. Med. Chern. 1975, 18, 905-909
13. Weinstein, H.; Chou, D.; Johnson, C. L.; Kang, S.; Green, J. P. Mol. Pharrnacol. 1976, 12, 738-745.
14. Gantz, I.; DelValle, J.; Wang, L.-d.; Tashiro, T.; Munzert, G.; Guo, Y.-J. Konda, Y.; Yamada, T. J. Biol. Chem. 1992, 267, 20840- 20843.
15. Rivero, I.A.; González, T.; Pina-Luis, G.; Díaz-Garcia M. E. J. Comb. Chem. 2005, 7, 46-53.

Published

2019-06-05

Issue

Section

Regular Articles