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