Synthesis and Modification of the Amyloid Peptide Sequence 37-42 of Aβ42 (AβPP): Efficient Synthesis of N-methylated Peptides, Expanding the Tools for Peptide Research

Authors

  • María Elena Rosas-Valdéz Universidad Autónoma del Estado de Morelos
  • Jaime Escalante Universidad Autónoma del Estado de Morelos
  • Ismael Bustos-Jaimes Universidad Nacional Autónoma de México
  • Ignacio Regla Universidad Nacional Autónoma de México (UNAM)
  • Alicia Boto Consejo Superior de Investigaciones Científicas (CSIC), La Laguna, Tenerife, Spain

DOI:

https://doi.org/10.29356/jmcs.v60i3.94

Keywords:

Amyloid, Peptides, AβPP, N-Methyl Amino Acids.

Abstract

We report the synthesis and characterization of N-alkyl modified peptides by efficient coupling of N-methyl amino acids in solution phase. As a model peptide, the segment 37-42 (GGVVIA) of the Aβ-42 amyloid peptide derived from the amyloid precursor protein (Aβ-PP) was chosen. This peptide and its derivatives with N-methyl groups on Val40 and Ile41 residues were synthesized and character-ized. Because the synthesis was performed in solution-phase, the procedure can be easily scaled up for the production of larger amounts of the peptides described in this work or any linear N-methyl peptide with potential therapeutic application.

Downloads

Download data is not yet available.

Author Biographies

Ismael Bustos-Jaimes, Universidad Nacional Autónoma de México

Facultad de Medicina

Ignacio Regla, Universidad Nacional Autónoma de México (UNAM)

Facultad de Estudios Superiores Zaragoza

Alicia Boto, Consejo Superior de Investigaciones Científicas (CSIC), La Laguna, Tenerife, Spain

Instituto de Productos Naturales y Agrobiología

References

Marx, V. Chem. Eng. 2005, 83, 17-24.

Banta, S.; Megeed, Z.; Casali, M.; Rege, K.; Yarmush, M.L. J. Nanosci. Nanotechnol. 2007, 7, 387-401.

Chatterjee, J.; Ovadia, O.; Zahn, G.; Marinelli, L.; Hoffman, A.; Gilon, C.; Kessler, H. J. Med. Chem. 2007, 50, 5878-5881.

Chatterjee, J.; Rechenmacher, F.; Kessler, H.; Angew. Chem. Int. Ed. 2013, 52, 254-269.

Di Gioia, M. L.; Leggio, A.; Liguori, A. J. Org. Chem. 2005, 70, 3892-3897.

Farahani, M.D.; Honarparvar, B.; Albericio, F.; Maguire, G. E. M.; Govender, T.; Arvidsson, P. I.; Kruger. H. G. Org. Biomol. Chem., 2014, 12, 4479-4490.

Rajarathnam, K.; Sykes, B. D.; Kay, C. M.; Dewald, B.; Geiser, T.; Baggiolini, M.; Clark-Lewis, I. Science, 1994, 264, 90-92.

Clark, T. D.; Buriak, J. M.; Kobayashi, K.; Isler, M. P.; McRee, D. E.; Ghadirim, M. R. J. Am. Chem. Soc. 1998, 120, 8949-8962.

Jarrett, J. T.; Berger, E. P.; Lansbury, P. T. Ann. N. Y. Acad. Sci. 1993, 695, 144-148.

Eckman, C. B.; Eckman, E. A. Neurol. Clin. 2007, 25, 669-682.

Hardy, J.A.; Higgins, G. A. Science, 1992, 286, 184-185.

Roychaudhuri, R.; Yang, M.; Hoshi, M. M.; Teplow, D. B., J. Biol. Chem., 2009, 284, 4749-4753.

Gordon, D. J.; Sciarretta, K. L.; Meredith, S. C. Biochemistry, 2001, 40, 8237-8245.

Ahmed, M.; Davis, J.; Aucoin, D.; Sato, T.; Ahuja, S.; Aimoto, S.; Elliott, J. I.; Van Nostrand W.; Smith, S. Nature Struct. Mol Biol., 2010, 17, 561-568.

Goldschmidt, L; Teng, PK; Riek, R.; Eisenberg, D. PNAS, 2010, 107(8), 3487-3492.

Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett., 1994, 35, 2279-2282.

Ayman, E. F.; Albericio, F. Chem. Rev. 2011, 111, 6557-6602.

Valeur, E.; Bradley, M. Chem. Soc. Rev., 2009, 38, 606-631.

Otera, J. Esterification: Methods, Reactions, and Application, Wi-ley-VCH: New York, 2003.

Wegman, M. A.; Elzinga, J. M.; Neeleman, E.; van Rantwijk, F.; Sheldon, R. A. Green Chemistry, 2001, 3, 61-64.

Biondini, D.; Brinchi, L.; Germani, R.; Goracci, L.; Savelli, G. Lett. Org. Chem., 2010, 7, 39-44.

Subiros-Funosas, R.; Acosta, G. A.; El-Faham, A.; Albericio, F. Tetrahedron Letters, 2009, 50, 6200-6202.

Pedersen, S. L.; Tofteng, A. P.; Malik, L.; Jensen, K. J., Chem. Soc. Rev., 2012, 41, 1826-1844.

Application Note BIO-0003, Microwave Synthesis: Racemization Studies, CEM Microwave-Enhanced Science.

Isidro-Llobet, A.; Álvarez, M.; Albericio, F., Chem. Rev. 2009, 109, 2455-2504.

Brown, Z. Z.; Schafmeister, C. E. J. Am. Chem. Soc. 2008, 130, 14382-14383.

Liu, Y.; Zhao, C.; Bergbreiter, D. E.; Romo, D. J. Org. Chem. 1998, 63, 3471-3473.

Teixidó, M.; Albericio, F.; Giralt, E. J. Peptide Res., 2005, 65,

-166.

Ovadia, O.; Greenberg, S.; Chatterjee, J.; Laufer, B.; Opperer, F.; Kessler, H.; Gilon, C.; Hoffman, A. Mol. Pharmaceutics, 2011, 8,

-487.

Malkov, A. V.; Vrankova, K.; Cerny, M.; Kocovsky, P. K. J. Org. Chem., 2009, 74, 8425-8427.

Borthwick, A. D. Chem. Rev. 2012, 112, 3641-3716.

Warfield, R.; Bardelang, P.; Saunders, H.; Chan, W. C.; Penfold, C.; James, R.; Thomas, N. R. Org. Biomol. Chem., 2006, 4, 3626-3638.

Downloads

Published

2017-10-12

Issue

Section

Regular Articles

Similar Articles

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