Abstract
Reversed-phase HPLC on chiral stationary phases was used to study the influence of the structure of purine and 2-aminopurine conjugates with chiral heterocyclic amines on the retention times. The optimum conditions for separation of enantiomers were found. The best parameters of separation of stereoisomers of all the compounds examined were achieved on a (S,S)-Whelk-O1 column in weakly alkaline aqueous methanol systems.
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H. Rosemeyer, Chem. Biodiversity, 2004, 1,361.
M. Legraverend, D. S. Grierson, Bioorg. Med. Chem., 2006, 14, 3987.
D. C. Baker, J. C. Hanvey, L. D. Hawkins, J. Murphy, Biochem. Pharmacol., 1981, 30, 1159.
M. Bessodes, G. Bastian, E. Abushanab, R. P. Panzica, S. P. Berman, E. J. Marcaccio, S.-F. Chen, J. D. Stoeckler, R. E. Parks, Jr., Biochem. Pharmacol., 1982, 31,879.
P. J. van Galen, A. H. van Bergen, C. Gallo-Rodriguez, N. Melman, M. E. Olah, A. P. Ijzerman, G. L. Stiles, K. A. Jacobson, Mol. Pharmacology, 1994, 45, 1101.
G. B. Evans, S. A. Cameron, A. Luxenburger, R. Guan, J. Suarez, K. Thomas, V. L. Schramm, P. C. Tyler, Bioorg. Med. Chem., 2015, 23, 5326.
A. Yu. Vigorov, V. P. Krasnov, D. A. Gruzdev, A. A. Men’shikova, A. M. Demin, G. L. Levit, V. N. Charushin, Mendeleev Commun., 2014, 24,35.
V. P. Krasnov, A. Yu. Vigorov, D. A. Gruzdev, G. L. Levit, A. M. Demin, I. A. Nizova, A. A. Tumashov, L. Sh. Sadretdinova, E. B. Gorbunov, V. N. Charushin, Russ. Chem. Bull., 2015, 64, 2106.
V. P. Krasnov, A. Yu. Vigorov, V. V. Musiyak, I. A. Nizova, D. A. Gruzdev, T. V. Matveeva, G. L. Levit, M. A. Kravchenko, S. N. Skornyakov, O. B. Bekker, V. N. Danilenko, V. N. Charushin, Bioorg. Med. Chem. Lett., 2016, 26, 2645.
D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Kravchenko, V. P. Krasnov, V. N. Charushin, Mendeleev Commun., 2017, 27,547.
V. P. Krasnov, D. A. Gruzdev, E. N. Chulakov, A. Yu. Vigorov, V. V. Musiyak, T. V. Matveeva, A. A. Tumashov, G. L. Levit, V. N. Charushin, Mendeleev Commun., 2015, 25,412.
D. A. Gruzdev, V. V. Musiyak, E. N. Chulakov, G. L. Levit, V. P. Krasnov, Chem. Heterocycl. Compd., 2015, 51,738.
B. Z. Eletskaya, I. D. Konstantinova, A. S. Paramonov, R. S. Esipov, D. A. Gruzdev, A. Yu. Vigorov, G. L. Levit, A. I. Miroshnikov, V. P. Krasnov, V. N. Charushin, Mendeleev Commun., 2016, 26,6.
W. A. Bowles, F. H. Schneider, L. R. Lewis, R. K. Robins, J. Med. Chem., 1963, 6,471.
D. A. Gruzdev, S. A. Vakarov, G. L. Levit, V. P. Krasnov, Chem. Heterocycl. Compd., 2014, 49, 1795.
N. Ullah, C. N. Fali, I. D. Spenser, Can. J. Chem., 2004, 82, 579.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1704–1709, September, 2018.
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Tumashov, A.A., Gruzdev, D.A., Vigorov, A.Y. et al. Analysis of racemic conjugates of purine with heterocyclic amines by chiral high-performance liquid chromatography. Russ Chem Bull 67, 1704–1709 (2018). https://doi.org/10.1007/s11172-018-2279-0
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DOI: https://doi.org/10.1007/s11172-018-2279-0