Abstract
The amidoalkylation reactions of a phosphonous acid containing a structural isostere of leucine in acetyl chloride and(or) acetic anhydride were studied under conditions of acid catalysis. A two-component method for the synthesis of a phosphinic analogue of alanylleucine using ethylidenebis(benzylcarbamate) was proposed.
This is a preview of subscription content, log in via an institution to check access.
REFERENCES
Notni, J., Simecek, J., Hermann, P., and Wester, H.-J., Chem. Eur. J., 2011, vol. 17, p. 14718. https://doi.org/10.1002/chem.201103503
Mucha, A., Molecules, 2012, vol. 17, p. 13530. https://doi.org/10.3390/molecules171113530
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 (Sigma Aldrich Inc.), 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
Georgiadis, D. and Dive, V., Top. Curr. Chem., 2015, vol. 360, p. 1. https://doi.org/10.1007/128_2014_571
Baylis, E.K., Campbell, C.D., and Dingwall, J.G., J. Chem. Soc. Perkin Trans. 1, 1984, p. 2845. https://doi.org/10.1039/P19840002845
McCleery, P.P. and Tuck, B., J. Chem. Soc. Perkin Trans. 1, 1989, p. 1319. https://doi.org/10.1039/P19890001319
Rozhko, L.F. and Ragulin, V.V., Amino Acids, 2005, vol. 29, no. 2, p. 139. https://doi.org/10.1007/s00726-005-0194-9
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., Rossinets, E.A., and Ragulin, V.V., Russ. J. Gen. Chem., 2011, vol. 81, no. 6, p. 1092. https://doi.org/10.1134/S1070363211060041
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
Eckhard, U., Huesgen, P.F., Schilling, O., Bellac, C.L., Butler, G.S., Cox, J.H., Dufour, A., Goebeler, V., Kappelhoff, R., Keller, U., Klein, T., Lange, P.F., Marino, G., Morrison, C.J., Prudova, A., Rodriguez, D., Starr, A.E., Wang, Y., and Overall, C.M., Matrix Biol., 2016, vol. 49, p. 37. https://doi.org/10.1016/j.matbio.2015.09.003
Stetter, H. and Kuhlmann, H., Synthesis, 1979, no. 1, p. 29. https://doi.org/10.1055/s-1979-28537
Funding
This work was performed as part of the governmental task of the Institute of Physiologically Active Substances of the Russian Academy of Sciences for 2019 (topic no. 00902019-008) with partial financial support from the Presidium of the Russian Academy of Sciences no. 14P, the Russian Foundation for Basic Research (grants no. 18-03-00959, 18-03-01123) and the Russian Science Foundation (grant no. 19-13-00294, chromatographic, spectral and elemental analysis).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Golovash, S.R., Grigorkevich, O.S., Tsebrikova, G.S. et al. Synthesis of Phosphinic Analogue of Alanylleucine. Russ J Gen Chem 90, 753–756 (2020). https://doi.org/10.1134/S1070363220040313
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363220040313