Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

Organic and Biomolecular Chemistry

Volumn 2, Issue 12, 2004, Pages 1712-1718

  Lara, Karen Ochoa ^a   Godoy Alcántar, Carolina ^b   Eliseev, Alexey V ^c   Yatsimirsky, Anatoly K ^d  

^a UNIVERSIDAD DE SONORA   (Mexico)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

^c UNIVERSITY AT BUFFALO   (United States)

^d UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ALGORITHMS; ANTIBIOTICS; AROMATIC COMPOUNDS; CARBOXYLIC ACIDS; COMPUTER SIMULATION; DERIVATIVES; ELECTROPHORESIS; ELECTROSTATICS; NEGATIVE IONS; ORGANIC POLYMERS; POTENTIAL ENERGY; SPECTROMETERS; TITRATION; X RAYS;

ENANTIOMERS; MACROCYCLIC RECEPTORS; QUATERNIZATION; RECEPTORS;

AMINO ACIDS;

ALKALOID; AMINO ACID; ANION; BENZYL DERIVATIVE; BENZYLISOQUINOLINE DERIVATIVE; CALIX(4)ARENE; CALIXARENE; CYCLODEXTRIN; DEUTERIUM OXIDE; PHENOL DERIVATIVE; TETRANDRINE;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ACETYLATION; ALKALOIDS; AMINO ACIDS; ANIONS; BENZYL COMPOUNDS; BENZYLISOQUINOLINES; CALIXARENES; CYCLODEXTRINS; DEUTERIUM OXIDE; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; STEREOISOMERISM;

EID: 3042707764     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b402698e     Document Type: Article

References (50)

1. (a) J. L. Sessler, P. I. Sanson, A. Andrievsky and V. Kral, in Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James and E. García-España, Wiley-VCH, New York, 1997; p. 369;
2. (b) R. J. Fitzmaurice, G. M. Kyne, D. Douheret and J. D. Kilburn, J. Chem. Soc., Perkin Trans. 1, 2002, 841.
3. (a) C. Bazzicalupi, A. Bencini, E. Berni, A. Bianchi, P. Fornasari, C. Giorgi and B. Valtancoli, Eur. J. Inorg. Chem., 2003, 1974;
4. (b) A. Livoreil, T. Hayashi, J. P. Sauvage and H. J. Ogoshi, Inorg. Biochem., 1997, 67, 117;
5. (c) R. Asif, D. S. Chung and J. I. Hong, Tetrahedron Lett., 2003, 44, 4335.
6. (a) K. Araki, M. Goto and S. Furusaki, Anal. Chim. Acta, 2002, 469, 173;
7. (b) P. S. Reddy, T. Kobayashi, M. Abe and N. Fujii, Eur. Polym. J., 2002, 38, 521.
8. (a) T. Fukahori, T. Ugawa and S. Nishikawa, J. Phys. Chem. A, 2002, 106, 9442;
9. (b) M. V. Rekharsky, F. P. Schwarz, Y. B. Tewari and R. N. Goldberg, J. Phys. Chem., 1994, 98, 10282;
10. (c) A. Cooper and D. D. MacNicol, J. Chem. Soc., Perkin Trans. 2, 760, 1978;
11. (d) M. Rekharsky and Y. Inoue, J. Am. Chem. Soc., 2000, 122, 4418.
12. (a) T. Kitae, T. Nakayama and K. Kano, J. Chem. Soc., Perkin Trans. 2, 207, 1998;
13. (b) Y. Liu, L. Li, X. Y. Li, H. Y. Zhang, T. Wada and Y. Inoue, J. Org. Chem., 2003, 68, 3646;
14. (c) R. Corradini, C. Paganuzzi, R. Marchelli, S. Pagliari, S. Sforza, A. Dossena, G. Galaverna and A. Duchateau, Chirality, 2003, 15, S30;
15. (d) M. Rekharsky, H. Yamamura, M. Kawai and Y. Inoue, J. Am. Chem. Soc., 2001, 123, 5360;
16. (e) Y. Liu, B. H. Han, A. D. Qi and R. T. Chen, Bioorg. Chem., 1997, 25, 155;
17. (f) Y. Liu, C.-C. You, H.-Y Zhang and Y.-L. Zhao, Eur. J. Org. Chem., 2003, 1415.
18. (a) G. Arena, A. Contino, F. G. Gulino, A. Magri, F. Sansone, D. Sciotto and R. Ungaro, Tetrahedron Lett., 1999, 40, 1597;
19. (b) F. Sansone, E. Chierici, A. Casnati and R. Ungaro, Org. Biomol. Chem., 2003, 1, 1802;
20. (c) F. P. Ballistreri, A. Notti, S. Pappalardo, M. F. Parisi and I. Pisagatti, Org. Lett., 2003, 5, 1071;
21. (d) E. K. Kazakova, A. U. Ziganshina, L. A. Muslinkina, J. E. Morozova, N. A. Makarova, A. R. Mustafina and W. D. Habicher, J. Inclusion Phenom. Macrocyclic Chem., 2002, 43, 65;
22. (e) J.-S. You, X.-Q. Yu, G.-L. Zhang, Q.-X. Xiang, J.-B. Lan and R.-G. Xie, Chem. Commun., 2001, 1819;
23. (f) F. Gasparrini, D. Misiti, M. Pierini and C. Villani, Org. Lett., 2002, 4, 3993;
24. (g) X. Chen, D.-M. Du and W.-T. Hua, Tetrahedron: Asymmetry, 2003, 14, 999;
25. (h) H. W. Zhao and W. T. Hua, J. Org. Chem., 2000, 65, 2933.
26. (a) O. Hayashida, L. Sebo and J. Rebek, Jr., J. Org. Chem., 2002, 67, 8291;
27. (b) N. Higashi, T. Koga and M. Niwa, ChemBioChem, 2002, 5, 448;
28. (c) P. Breccia, M. Van Gool, R. Perez-Fernandez, S. Martin-Santamaria, F. Gago, P. Prados and J. de Mendoza, J. Am. Chem. Soc., 2003, 125, 8270;
29. (d) G. M. Kyne, M. E. Light, M. B. Hursthouse, J. de Mendoza and J. D. Kilburn, J. Chem. Soc., Perkin Trans. 1, 2001, 1258;
30. (e) C. P. Du, J. S. You, X. Q. Yu, C. L. Liu, J. B. Lan and R. B. Xie, Tetrahedron: Asymmetry, 2003,14, 3651.
31. (a) O. Hayashida, K. Ono, Y. Hisaeda and Y. Murakami, Tetrahedron, 1995, 51, 8423;
32. (b) K. H. Krawinkler, N. M. Maier, R. Ungaro, F. Sansone, A. Casnati and W. Lindner, Chirality, 2003, 15, 817.
33. (a) T. J. Ward and A. B. Farris III, J. Chromatogr., A, 2001, 906, 73;
34. (b) D. W. Armstrong, M. P. Gasper and K. L. Rundlett, J. Chromatogr., A, 1995, 689, 285;
35. (c) A. Berthod, Y. Liu, C. Bagwill and D. W. Armstrong, J. Chromatogr., A, 1996, 731, 123;
36. (d) C. Desiderio and S. Fanali, J. Chromatogr., A, 1998, 807, 37.
37. (a) C. Godoy-Alcántar, A. V. Eliseev and A. K. Yatsimirsky, Bioorg. Med. Chem. Lett., 1995, 5, 2993;
38. (b) C. Godoy-Alcántar, M. I. Nelen, A. V. Eliseev and A. K. Yatsimirsky, J. Chem. Soc., Perkin Trans. 2, 1999, 353.
39. 5f The reasons for this increased affinity and selectivity are not clear.
40. (a) G. Hembury, M. Rekharsky, A. Nakamura and Y. Inoue, Org. Lett., 2000, 2, 3257;
41. (b) S. Li and W. C. Purdy, Anal. Chem., 1992, 64, 1405.
42. C. M. Pearce, U. Gerhard and D. H. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 159.
43. K. O. Lara, C. Godoy-Alcántar, I. L. Rivera, A. V. Eliseev and A. K. Yatsimirsky, J. Phys. Org. Chem., 2001, 14, 453.
44. J. C. Gilmore, R. F. Bryan and S. M. Kupchan, J. Am. Chem. Soc., 1976, 98, 1947.
45. H.-J. Schneider, F. Hacket and V. Rüdiger, Chem. Rev., 1998, 98, 1755 and references therein.
46. D. H. Williams, J. P. L. Cox, A. J. Doig, M. Gardner, U. Gerhard, P. T. Kaye, A. R. Lal, I. A. Nicholls, C. Salter and R. C. Mitchell, J. Am. Chem. Soc., 1991, 113, 7020.
47. R. J. Abraham, S. C. M. Fell and K. M. Smith, Org. Magn. Reson., 1977, 9, 367.
48. J. P. Brown, L. Terenius, J. Feeney and A. S. V. Burgen, Mol. Pharmacol., 1975, 11, 126.
49. (a) S. Kotha, Acc. Chem. Res., 2003, 36, 342;
50. (b) S. E. Gibson (née Thomas), N. Guillo and M. J. Tozer, Tetrahedron, 1999, 55, 585.