Abstract
Methods were developed for the first time for the modification of the natural neuropeptides Ile–Gly–Leu and Leu–Gly–Leu simultaneously with the phosphonate moiety and the triazole ring or solely with the triazole ring by means of click chemistry. All of the peptidomimetics synthesized were isolated as a mixture of diastereomers and were characterized by spectroscopic methods.
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References
L. Pickart, J. Biomater, Sci. Polym. Ed., 2008, 19, 969.
M. Yu. Smakhtin, A. I. Konoplya, L. A. Severýanova, I. I. Bobyntsev, A. A. Kurtseva, V. Yu. Cherdakov, Kursk. Nauch.Prakt. Vestn. "Chelovek i Ego Zdorové" [Kursk Sci. Practic Bull "Man and Its Health"], 2006, 3, 11 (in Russian).
M. R. Ahmed, S. H. Basha, D. Gopinath, R. Muthusamy, R. Jayakumar, J. Peripher. Nerv. Syst., 2005, 10, 17.
V. Kh. Khavinson, A. Yu. Solovév, S. I. Tarnovskaya, N. S. Lińkova, Biol Bull Rev., 2013, 3, 451 [Usp. Sovrem. Biol.], 2013, 133, 310.
R. Mileusnic, C. L. Lancashire, A. N. B. Johnston, S. P. R. Rose, Eur. J. Neurosci., 2000, 12, 4487.
K. Bifulco, I. Longanesi-Cattani, L. Gargiulo, O. Maglio, M. Cataldi, M. De Rosa, M. P. Stoppelli, V. Pavone, M. V. Carriero, FEBS Lett., 2009, 582, 1141.
R. Mileusnic, S. P. R. Rose, Eur. Pat. EP 1381627, 2004.
E. D. Matveeva, E. A. Podrugina, M. V. Prisyazhnyi, S. O. Bachurin, N. S. Zefirov, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 200 [Izv. Akad. Nauk, Ser. Khim., 2010, 196].
R. Mileusnic, C. L. Lancashire, S. P. R. Rose, Ann._N. Y. Acad. Sci., 2005, 1048, 149.
R. Huisgen, G. Szeimies, L. Meldal, J. Org. Chem., 1967, 100, 2494.
V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596.
Yu. L. Angell, K. Burgess, Chem. Soc. Rev., 2007, 36, 1674.
O. N. Zefirova, N. S. Zefirov, Vestn. Mosk. Univ., Ser. Khim., 2002, 43, No. 4, 251 [Vestn. Mosk. Univ., Ser. Khim. (Engl. Transl.), 2002, 43].
D. Sikora, T. Nonas, T. Gayda, Tetrahedron, 2001, 57, 1619.
D. A. McLeod, R. I. Brinkworth, J. A. Ashley, K. D. Janda, P. Wirsching, Med. Chem. Lett., 1991, 1, 653.
T. Gajda, Synthesis, 1990, 8, 717.
S. Haridas, R. P. Verma, S. Sadanandan, B. G. Kacheshwar, Tetrahedron, 2011, 67, 1873.
R. Srinivasan, L. P. Tan, H. Wu, P.-Y. Yang, K. A. Kalesh, S. Q. Yao, Org. Biomol. Chem., 2009, 7, 1821.
R. Ramapanicker, R. Gupta, R. Megha, S. Chandrasekaran, Int. J. Peptides, 2011, doi: 10.1155/2011/854952.
S. P. Bew, G. D. Hiatt-Gipson, J. Org. Chem., 2010, 75, 3897.
E. V. Sharova, G. K. Genkina, E. V. Matveeva, I. B. Goryunova, E. I. Goryunov, O. I. Artyushin, V. K. Brel, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 2546 [Izv. Akad. Nauk, Ser. Khim., 2014, 2546].
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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2172–2177, September, 2015.
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Artyushin, O.I., Sharova, E.V., Yarkevich, A.N. et al. Design of phosphonate analogs of short peptides by “click” chemistry. Russ Chem Bull 64, 2172–2177 (2015). https://doi.org/10.1007/s11172-015-1134-9
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DOI: https://doi.org/10.1007/s11172-015-1134-9