Abstract
In the scope of a broader study focused on glutamate receptors regulators, we have been engaged in synthesis, analysis and pharmacological characterization of rigid analogues of glutamic acid. These compounds exhibited the bioisosteric replacement of the distal carboxylic group with the sulfonic one. Besides the sophisticated synthetic approach, we targeted preparation of a series of cyclopropyl-containing sulfonyl amino acids and development of a chromatographic enantioselective method suitable for distinguishing and quantifying the resulting isomers. Due to chelating ability, the chiral ligand-exchange chromatography (CLEC) was used for diastereo- and enantioseparation of the synthesized compounds. The CLEC-based enantioseparation was achieved by using a chiral mobile phase (CMP) system with N,N-dimethyl-(S)-phenylalanine [(S)-DMP] as the chiral selector. Only one of the investigated enantiomeric pairs was undiscriminated with the employed CLEC–CMP system which, very importantly, produced the simultaneous diastereo- and enantioseparation of two compounds of the series. Furthermore, the large α and RS values computed for three enantiomer pairs could be a good basis for a successful scale-up to a semi-preparative level.
Similar content being viewed by others
References
Talele, T.T., J. Med. Chem., 2016, vol. 59, p. 8712. doi 10.1021/acs.jmedchem.6b00472
Zhang, T., Shen, W., Liu, M., Zhang, R., Wang, M., Li, L., Wang, B., Guo, H., and Lu, Y., Eur. J. Med. Chem., 2015, vol. 104, p. 73. doi 10.1016/j.ejmech.2015.09.030
Malcomson, T., Yalekci, K., Borrello, M.T., Ganesan, A., Semina, E., De Kimpe, N., Mangelinckx, S., and Ramsay, R.R., FEBS J., 2015, vol. 282, p. 3190. doi 10.1111/febs.13260
Lakkaraju, S.K., Mbatia, H., Hanscom, M., Zhao, Z., Wu, J., Stoica, B., MacKerell A.D., Jr., Faden, A.I., and Xue, F., Bioorg. Med. Chem. Lett., 2015, vol. 25, p. 2275. doi 10.1016/j.bmcl.2015.04.042
Takahashi, H., Riether, D., Bartolozzi, A., Bosanac, T., Berger, V., Binetti, R., Broadwater, J., Chen, Z., Crux, R., De Lombaert, S., Dave, R., Dines, J.A., Fadra-Khan, T., Flegg, A., Garrigou, M., Hao, M.H., Huber, J., Hutzler, J.M., Kerr, S., Kotey, A., Liu, W., Lo, H.Y., Loke, P.L., Mahaney, P.E., Morwick, T.M., Napier, S., Olague, A., Pack, E., Padyana, A.K., Thomson, D.S., Tye, H., Wu, L., Zindell, R.M., Abeywardane, A., and Simpson, T., J. Med. Chem., 2015, vol. 58, p. 1669. doi 10.1021/jm501185j
Zhang, D., Pillow, T.H., Ma, Y., Cruz-Chuh, J.D., Kozak, K.R., Sadowsky, J.D., Lewis Phillips, G.D., Guo, J., Darwish, M., Fan, P., Chen, J., He, C., Wang, T., Yao, H., Xu, Z., Chen, J., Wai, J., Pei, Z., Hop, C.E.C.A., Khojasteh, S.C., and Dragovich, P.S., ACS Med. Chem. Lett., 2016, vol. 7, p. 988. doi 10.1021/acsmedchemlett.6b00233
Pellicciari, R., Natalini, B., Marinozzi, M., Selvi, L., Chiorri, C., Monahan, J.B., Lanthorn, T.H., and Snyder, J.P., in Frontiers in Excitatory Amino Acid Research, Cavalheiro, E.A., Lehman, J., and Turski, L., Eds., New York: Alan R. Liss, Inc., Scientific, Medical and Scholarly Publications, 1988, vol. 46, p. 67. ISBN: 0845127500, 9780845127506
Pellicciari, R., Natalini, B., Marinozzi, M., Monahan, J.B., and Snyder, J.P., Tetrahedron Lett., 1990, vol. 31, p. 139. doi 10.1016/S0040-4039(00)94355-7
Monahan, J.B., Hood, W.F., Compton, R.P., Cordi, A.A., Snyder, J.P., Pellicciari, R., and Natalini, B., Neurosci. Lett., 1990, vol. 112, p. 328. doi 10.1016/0304-3940(90) 90225-X
Dappen, M.S., Pellicciari, R., Natalini, B., Monahan, J.B., Chiorri, C., and Cordi, A.A., J. Med. Chem., 1991, vol. 34, p. 161. doi 10.1021/jm00105a024
Pellicciari, R., Natalini, B., Marinozzi, M., Sadeghpour, B.M., Cordi, A.A., Lanthorn, T.H., Hood, W.F., and Monahan, J.B., Il Farmaco, 1991, vol. 46, p. 1243.
Marinozzi, M., Natalini, B., Ni, M.H., Costantino, G., Pellicciari, R., and Thomsen, C., Il Farmaco, 1995, vol. 50, p. 327.
Pellicciari, R., Marinozzi, M., Natalini, B., Costantino, G., Luneia, R., Giorgi, G., Moroni, F., and Thomsen, C., J. Med. Chem., 1996, vol. 39, p. 2259. doi 10.1016/S0021-9673(99)01281-9
Natalini, B., Capodiferro, V., De Luca, C., and Espinal, R., J. Chromatogr. A, 2000, vol. 873, p. 283. doi 10.1016/S0021-9673(99)01281-9
Sardella, R., Lämmerhofer, M., Natalini, B., and Lindner, W., Chirality, 2008, vol. 20, p. 571. doi 10.1002/chir.20529
Pellicciari, R., Marinozzi, M., Macchiarulo, A., Fulco, M.C., Gafarova, J., Serpi, M., Giorgi, G., Nielsen, S., and Thomsen, C., J. Med. Chem., 2007, vol. 50, p. 4630. doi 10.1021/jm070322e
Langdon, S.R., Ertl, P., and Brown, N., Mol. Inf., 2010, vol. 29, p. 366. doi 10.1002/minf.201000019
Davankov, V.A. and Rogozhin, S.V., J. Chromatogr., 1971, vol. 60, p. 280. doi 10.1016/S0021-9673(00)95566-3
Davankov, V.A., J. Chromatogr. A, 1994, vol. 666, p. 55. doi 10.1016/0021-9673(94)80370-6
Wernicke, R., J. Chromatogr. Sci., 1985, vol. 23, p. 39. doi 10.1093/chromsci/23.1.39
Natalini, B., Marinozzi, M., Bade, K., Sardella, R., Thomsen, C., and Pellicciari, R., Chirality, 2004, vol. 16, p. 314. doi 10.1002/chir.20027
Natalini, B., Marinozzi, M., Sardella, R., Macchiarulo, A., and Pellicciari, R., J. Chromatogr. A, 2004, vol. 1033, p. 363. doi 10.1016/j.chroma.2004.01.054
Natalini, B., Sardella, R., Macchiarulo, A., Marinozzi, M., Camaioni, E., Pellicciari, R., in Advances in Chromatography, Grushka, E. and Grinberg, N., Eds, CRC Press, Taylor and Francis Group, Boca Raton, 2011, vol. 49, p. 71. doi 10.1201/b10721-4
Davankov, V.A., J. Chromatogr. A, 2003, vol. 1000, p. 891. doi 10.1016/S0021-9673(03)00304-2
Davankov, V.A., Kurganov, A.A., and Ponomareva, T.M., J. Chromatogr., 1988, vol. 452, p. 309. doi 10.1016/S0021-9673(01)81455-2
Galaverna, G., Paganuzzi, M.C., Corradini, R., Dossena, A., and Marchelli, R., Electrophoresis, 2001, vol. 22, p. 3171. doi 10.1002/1522-2683(200109)
Davankov, V.A., Enantiomer, 2000, vol. 5, p. 209.
Sardella, R., Ianni, F., Lisanti, A., Scorzoni, S., Marinozzi, M., and Natalini, B., Crit. Rev. Anal. Chem., 2015, vol. 45, p. 323. doi 10.1080/10408347.2014.937851
Davankov, V.A., Bochkov, A.S., and Belov, Y.P., J. Chromatogr., 1981, vol. 218, p. 547. doi 10.1016/S0021-9673(00)82079-8
Carotti, A., Ianni, F., Camaioni, E., Pucciarini, L., Marinozzi, M., Sardella, R., and Natalini, B., J. Pharm. Biomed. Anal., 2017, in press. doi 10.1016/j.jpba.2017.02.009
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Sardella, R., Ianni, F., Pucciarini, L. et al. Cyclopropyl-containing sulfonyl amino acids: Exploring the enantioseparation through chiral ligand-exchange chromatography. Russ J Gen Chem 87, 1079–1084 (2017). https://doi.org/10.1134/S1070363217050309
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363217050309