Synthesis of Peptides Histamine H2 Receptors in Solid-Phase Assisted by Microwave
DOI:
https://doi.org/10.29356/jmcs.v54i3.929Keywords:
Solid Phase, Peptide, MicrowaveAbstract
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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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.
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