Abstract
Reactions of L-methionine, L-serine, and L-valine with 5-substituted-2-hydroxybenzene-1,3-dicarbaldehydes gave a series of chiral Schiff base pincer ligands which were reduced to the corresponding diamines. The new Schiff base ligands reacted with copper(II) chloride to form dinuclear copper complexes which were found to be capable of recognizing tyrosine enantiomers in aqueous solution. The structure of the complexes was determined on the basis of their spectral parameters.
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Cherevin, M.S., Gulevich, T.G., Borisova, N.E., Zubreichuk, Z.P., Kolesnikov, G.V., Reshetova, M.D., and Knizhnikov, V.A., Russ. J. Org. Chem., 2007, vol. 43, p. 1567.
Lee, Ch.-S., Teng, P.-F., Wong, W.-L., Kwong, H.-L., and Chan, A.S.C., Tetrahedron, 2005, vol. 61, p. 7924.
Turgut, Y., Demirel, N., and Hosgoren, H., J. Inclusion Phenom. Macrocycl. Chem., 2006, vol. 54, p. 29.
Sawada, M., Okumura, Y., Yamada, H., Takai, Y., Takahashi, Sh., Kaneda, T., Hirose, K., and Misumi, S., Org. Mass Spectrom., 1993, vol. 28, p. 1525.
Liu, Sh.-Y., He, Y.-B., Qing, G.-Y., Xu, K.-X., and Qin, H.-J., Tetrahedron: Asymmetry, 2005, vol. 16, p. 1527.
Qing, G.-Y., He, Y.-B., Zhao, Y., Hu, Ch.-G., Liu, Sh.-Y., and Yang, X., Eur. J. Org. Chem., 2006, p. 1574.
Lu, G., Liu, F., Song, W., He, W., Prados, P., and de Mendoza, J., Mater. Sci. Eng. C, 1999, vol. 10, p. 29.
Liu, F., Lu, G.-Y., He, W.-J., Liu, M.-H., and Zhu, L.-G., Thin Solid Films, 2004, vol. 468, p. 244.
Du, C.-P., You, J.-S., Yu, X.-Q., Liu, Ch.-L., Lana, J.-B., and Xie, R.-G., Tetrahedron: Asymmetry, 2003, vol. 14, p. 3651.
Dowden, J., Edwards, P.D., Flack, S.S., and Kilburn, J.D., Chem. Eur. J., 1999, vol. 5, p. 79.
Liu, Y., You, Ch.-Ch., Zhang, H.-Y., and Zhao, Y.-L., Eur. J. Org. Chem., 2003, p. 1415.
Belokon’, Y.N., Pritula, L.K., Tatarov, V.I., Bakhmutov, V.I., Gusev, D.G., Saporovskaya, M.B., and Belikov, V.M., J. Chem. Soc., Dalton Trans., 1990, p. 1873.
Belokon’, Yu.N., Pure Appl. Chem., 1992, vol. 64, p. 1917.
Kim, H.-J., Asif, R., Chung, D.S., and Hong, J.-I., Tetrahedron Lett., 2003, vol. 44, p. 4335.
Ye, G., Chai, Y.R., Zhou, L., Li, Y., and Zhang, L., Anal. Sci., 2007, vol. 23, p. 171.
Illán-Cabeza, N.A., Moreno-Carretero, M.N., and Costa Pessoa, J., Inorg. Chim. Acta, 2005, vol. 358, p. 2246.
Jakubke, H.-D. and Jeschkeit, H., Amino Acids, Peptides, and Proteins: An Introduction, New York: Wiley, 1977. Translated under the title Aminokisloty. Peptidy. Belki, Moscow: Mir, 1985, p. 33.
Nakamoto, K., Morimoto, Y., and Martell, A.E., J. Am. Chem. Soc., 1961, vol. 83, p. 4528.
Sorrell, T.N., Jameson, D.L., and O’Connor, Ch.J., Inorg. Chem., 1984, vol. 23, p. 190.
Analytical Methods in Supramolecular Chemistry, Schalley, Ch.A., Weinheim: Wiley, 2007, p. 484.
Gershkovich, A.A. and Kibirev, V.K., Sintez peptidov. Reagenty i metody (Synthesis of Peptides. Reagents and Methods), Kiev: Naukova Dumka, 1987, 264.
Lindoy, L.F., Meehan, G.V., and Svenstrup, N., Synthesis, 1998, p. 1029.
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Original Russian Text © N.E. Borisova, V.A. Knizhnikov, T.G. Gulevich, M.Yu. Seliverstov, E.A. Borisov, M.D. Reshetova, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 377–385.
For communication II, see [1].
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Borisova, N.E., Knizhnikov, V.A., Gulevich, T.G. et al. Pincer ligands based on α-amino acids: III. New ligands based on 4-substituted phenols and their copper complexes. Enantioselective recognition of tyrosine. Russ J Org Chem 45, 365–373 (2009). https://doi.org/10.1134/S107042800903004X
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DOI: https://doi.org/10.1134/S107042800903004X