Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis

Authors

  • Javier Eduardo García Castañeda Universidad Nacional de Colombia
  • Cristian Francisco Vergel Galeano Universidad Nacional de Colombia
  • Zuly Jenny Rivera Monroy Universidad Nacional de Colombia
  • Javier Eduardo Rosas Pérez Universidad Nacional de Colombia

DOI:

https://doi.org/10.29356/jmcs.v58i4.47

Keywords:

Synthetic Peptide, piperidine, 4-methylpiperidine, Fmoc removal reaction, Solid Phase Peptide Synthesis

Abstract

Solid phase peptide synthesis using the Fmoc/t-Bu strategy (SPPS-Fmoc/tBu) is the most widely used methodology for obtaining synthetic peptides. In this paper, we evaluate the viability of using 4-methylpiperidine as a reagent for deprotection of the amino acid alpha amino group in SPPS-Fmoc/tBu. For this purpose, the peptide (RRWQWRMKKLG) was simultaneously synthesized using 4-methylpiperidine or piperidine for Fmoc removal reagent. The obtained products had similar purities and yields. Finally, 21 peptides were synthesized using 4-methylpiperidine. Our results suggest that is possible to obtain synthetic peptides efficiently by the strategy SPPS-Fmoc/tBu when 4-methylpiperidine was used as reagent to remove Fmoc groups N-alpha protected amino acids.

Downloads

Download data is not yet available.

Author Biographies

Javier Eduardo García Castañeda, Universidad Nacional de Colombia

Departamento de Farmacia

Cristian Francisco Vergel Galeano, Universidad Nacional de Colombia

Departamento de Farmacia

Zuly Jenny Rivera Monroy, Universidad Nacional de Colombia

Departmento de Química, Facultad de Ciencias

Javier Eduardo Rosas Pérez, Universidad Nacional de Colombia

Departamento de Farmacia

References

Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149-2154. DOI: https://doi.org/10.1021/ja00897a025

Carpino, L.A. Acc. Chem. Res. 1987, 20, 401-407. DOI: https://doi.org/10.1021/ar00143a003

Carpino, L.A.; Han, G.Y. J. Am. Chem. Soc. 1970, 92, 5748-5749. DOI: https://doi.org/10.1021/ja00722a043

Athertohn, E.; Fox, H.; Harkissc, D.; Logan, J.C.; Sheppard, R.C; Williams, B.J. J. Chem. Soc., Chem. Commun. 1978, 13, 537-539. DOI: https://doi.org/10.1039/c39780000537

Carpino, L.A.; Han, G.Y. J Org. Chem. 1972, 37, 3404-3409. DOI: https://doi.org/10.1021/jo00795a005

Fields, G.; Noble, R. Int. J. Peptide Protein Res. 1990, 35, 161-214. DOI: https://doi.org/10.1111/j.1399-3011.1990.tb00939.x

Larsen, B.; Holm, A. Int. J. Peptide Protein Res. 1994, 43, 1-9. DOI: https://doi.org/10.1111/j.1399-3011.1994.tb00368.x

Zinieris, N.; Leondiadis, L.; Ferderigos, N. J. Comb. Chem. 2005, 7, 4-6. DOI: https://doi.org/10.1021/cc049872d

Várady, L.; Rajur, S.; Nicewonger, R.; Guo, M.; Ditto, L. J. Chrom. A. 2000, 869, 171-179. DOI: https://doi.org/10.1016/S0021-9673(99)00844-4

Bodanszky, M.; Deshmane, S.; Martinez, J. J. Org. Chem. 1979, 44, 1622-1625. DOI: https://doi.org/10.1021/jo01324a008

Rawer, S.; Roeder, R.; Henklein, P. J Pept Sci. 2006, 12, Issue S1. 29th European Peptide Symposium.

Orain, D.; Ellard, J.; Bradley, M. J. Comb. Chem. 2002, 4, 1-16. DOI: https://doi.org/10.1021/cc0001093

Sheppeck, J.E.; Kar, H.; Hong, H. Tetrah. Lett. 2000, 41, 5329-5333. DOI: https://doi.org/10.1016/S0040-4039(00)00853-4

Isidro-Llobet, A.; Alvarez, M.; Albericio, F. Chem. Rev. 2009, 109, 2455-2504. DOI: https://doi.org/10.1021/cr800323s

Carpino, L.A.; Sadat-Aalaee, D.: Beyermann, M. J. Org. Chem. 1990, 55, 1673-1675. DOI: https://doi.org/10.1021/jo00292a050

Beyermann, M.; Bienert, M.; Niedrich, H.; Carpino, L.; Sadat-Aalaee, D. J. Org. Chem. 1990, 55, 721-728. DOI: https://doi.org/10.1021/jo00289a056

Hachmann, J.; Lebl, M. J. Comb. Chem. 2006, 8, 149. DOI: https://doi.org/10.1021/cc050123l

Shiryaev, S.; Kozlov, I.; Ratnikov, B.; Smith, J.; Lebl, M.; Strongin, A.Y. Biochem. J. 2007, 401, 743-752. DOI: https://doi.org/10.1042/BJ20061136

Sarin, V.K.; Kent, S.B.; Tam, J.P.; Merrifield, R.B. Anal.Biochem. 1981, 117, 147-157. DOI: https://doi.org/10.1016/0003-2697(81)90704-1

Jensen, J.K.; Alsina, J.; Songster, F.M.; Vagner, J.; Albericio, F.; Barany, G.J. Am. Chem. Soc. 1998, 120, 5441. DOI: https://doi.org/10.1021/ja974116f

×

Downloads

Published

2017-10-12

Issue

Section

Regular Articles
x

Similar Articles

<< < 5 6 7 8 9 10 11 12 13 14 > >> 

You may also start an advanced similarity search for this article.

Loading...