Abstract
The amidoalkylation of a phosphonous acid containing a structural isostere of diethyl glutamiate, using ethyl carbamate and 3-(methylthio)propionaldehyde, was proposed for the synthesis of NC(O)OEt-protected phosphinic pseudo-Met-Glu-peptide. Subsequent adamantyl protection of the phosphorylic function and hydrolysis of carboxylic groups made it possible to obtain phosphinic Met-[P]-Glu peptide in the form of cyclic glutamate anhydride. It was found that the latter reacts with the third amino acid component histidine to form the phosphinic Met-[P]-Glu-γ-His tripeptide.
This is a preview of subscription content, log in via an institution to check access.
Notes
Hereafter [P] = ψ[P(O)(OH)CH2]. The name of acid phosphinic dipeptides has recently been abbreviated in the literature as phosphinic peptides by analogy with literary sources in English. Therefore, the term “phosphinic peptides” is used in this work.
REFERENCES
Shevchenko, K.V., Nagaev, I.Yu., Andreeva, L.A., Shevchenko, V.P., and Myasoedov, N.F., Dokl. Biol. Sci., 2013, vol. 449, no. 1, p. 110. https://doi.org/10.1134/S0012496613020166
Vinyukov, A.V., Dmitriev, M.E.,Andreeva, L.A., Ustyugov, A.A., Shevchenko, V.P., Sidoruk, K.N., Lednev, B.V., Freyman, V.M., Dobrovolskiy, Y.A., Ragulin, V.V., and Myasoedov, N.F., Biochem. Biophys. Res. Commun., 2021, vol. 539, p. 15. https://doi.org/10.1016/j.bbrc.2020.12.087
Collinsova, M. and Jiracek, J., Curr. Med. Chem., 2000, vol. 7, no. 6, p. 629. https://doi.org/10.2174/0929867003374831
Dive, V., Georgiadis, D., Matziari, M., Makaritis, A., Beau, F., Cuniasse, P., and Yiotakis, A., Cell. Mol. Life Sci., 2004, vol. 61, p. 2010. https://doi.org/10.1007/s00018-004-4050-y
Mucha, A., Molecules, 2012, vol. 17, no. 11, p. 13530. https://doi.org/10.3390/molecules171113530
Georgiadis, D. and Dive, V., Top. Curr. Chem., 2015, vol. 360, p. 1. https://doi.org/10.1007/128_2014_571
Zinc Metalloproteases in Health and Disease, Hooper, N.M., Ed., London: Taylor and Francis, 1996, p. 153.
Hori, M. and Nishida, K., Cardiovasc. Res., 2009, vol. 81, no. 3, p. 457. https://doi.org/10.1093/cvr/cvn335
Whittaker, M. and Ayscough, A., Celltransmissions, 2001, vol. 17, no. 1, p. 3.
Pirad, B. and Matter, H., J. Med. Chem., 2006, vol. 49, no. 1, p. 51. https://doi.org/10.1021/jm050363f
Dmitriev, M.E. and Ragulin, V.V., Tetrahedron Lett., 2010, vol. 51, no. 19, p. 2613. https://doi.org/10.1016/j.tetlet.2010.03.020
Dmitriev, M.E. and Ragulin, V.V., Tetrahedron Lett., 2012, vol. 53, no. 13, p. 1634. https://doi.org/10.1016/j.tetlet.2012.01.094
Dmitriev, M.E., Golovash, S.R., Borodachev, A.V., and Ragulin, V.V., J. Org. Chem., 2021, vol. 86, no. 1, p. 593. https://doi.org/10.1021/acs.joc.0c02259
Dmitriev, M.E., Vinyukov, A.V., Ragulin, V.V., and Myasoedov, N.F., Russ. J. Gen. Chem., 2015, vol. 85, no. 9, p. 2215. https://doi.org/10.1134/S1070363215090315
Yiotakis, A., Vassiliou, S., Jiracek, J., and Dive, V., J. Org. Chem., 1996, vol. 61, no. 19, p. 6601. https://doi.org/10.1021/jo9603439
Georgiadis, D., Dive, V., and Yiotakis, A., J. Org. Chem., 2001, vol. 66, no. 20, p. 6604. https://doi.org/10.1021/jo0156363
Kalyanam, N. and Majeed, M., Chim. Oggi., 2008, vol. 26, no. 3, p. 44.
Amino, Y., Nakazawa, M., Kaneko, M., Miyaki, T., Miyamura, N., Maruyama, Y., and Eto, Y., Chem. Pharm. Bull., 2016, vol. 64, no. 8, p. 1181. https://doi.org/10.1248/cpb.c16-00293
Funding
The work was partially supported by the Russian Science Foundation (grant no. 23-23-00158).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Dmitriev, M.E., Shevchenko, K.V., Shevchenko, V.P. et al. Synthesis of Phosphinic Pseudomethionyl-Glutamyl-Histidine. Russ J Gen Chem 93, 2022–2028 (2023). https://doi.org/10.1134/S1070363223080108
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223080108