Enantioselective binding and extraction of zwitterionic amino acids by chiral lanthanide complexes

Chemical Communications

Volumn , Issue 4, 1996, Pages 477-478

  Tsukube, Hiroshi ^a   Uenishi, Jun Ichi ^b   Kanatani, Tatsuya ^b   Itoh, Hiroyuki ^b   Yonemitsu, Osamu ^b  

^a Osaka Prefecture University   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002541608     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000477     Document Type: Article

References (19)

1. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; S. S. Peacock, D. M. Walba, F. C. A. Gaeta, R. C. Hodgeson and D. J. Cram, J. Am. Chem. Soc., 1980, 102, 2043; G. Li and W. C. Still, J. Org. Chem., 1991, 56, 6964; I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc., 1993, 115, 4318; J. S. Albert, M. S. Goodman and A. D. Hamilton, J. Am. Chem. Soc., 1995, 117, 1143.
2. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; S. S. Peacock, D. M. Walba, F. C. A. Gaeta, R. C. Hodgeson and D. J. Cram, J. Am. Chem. Soc., 1980, 102, 2043; G. Li and W. C. Still, J. Org. Chem., 1991, 56, 6964; I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc., 1993, 115, 4318; J. S. Albert, M. S. Goodman and A. D. Hamilton, J. Am. Chem. Soc., 1995, 117, 1143.
3. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; S. S. Peacock, D. M. Walba, F. C. A. Gaeta, R. C. Hodgeson and D. J. Cram, J. Am. Chem. Soc., 1980, 102, 2043; G. Li and W. C. Still, J. Org. Chem., 1991, 56, 6964; I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc., 1993, 115, 4318; J. S. Albert, M. S. Goodman and A. D. Hamilton, J. Am. Chem. Soc., 1995, 117, 1143.
4. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; S. S. Peacock, D. M. Walba, F. C. A. Gaeta, R. C. Hodgeson and D. J. Cram, J. Am. Chem. Soc., 1980, 102, 2043; G. Li and W. C. Still, J. Org. Chem., 1991, 56, 6964; I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc., 1993, 115, 4318; J. S. Albert, M. S. Goodman and A. D. Hamilton, J. Am. Chem. Soc., 1995, 117, 1143.
5. J.-P. Behr and J.-M. Lehn, J. Am. Chem. Soc., 1973, 95, 6108; S. S. Peacock, D. M. Walba, F. C. A. Gaeta, R. C. Hodgeson and D. J. Cram, J. Am. Chem. Soc., 1980, 102, 2043; G. Li and W. C. Still, J. Org. Chem., 1991, 56, 6964; I. H. Chu, D. V. Dearden, J. S. Bradshaw, P. Huszthy and R. M. Izatt, J. Am. Chem. Soc., 1993, 115, 4318; J. S. Albert, M. S. Goodman and A. D. Hamilton, J. Am. Chem. Soc., 1995, 117, 1143.
6. (a) F. P. Schmidchen, J. Org. Chem., 1986, 51, 5161;
7. (b) J. Rebek, B. Askew, D. Nemeth and K. Parris, J. Am. Chem. Soc., 1987, 109, 2432;
8. (c) L. K. Mohler and A. W. Czarnik, J. Am. Chem. Soc., 1993, 115, 7037;
9. (d) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege and R. Goddard, J. Am. Chem. Soc., 1994, 116, 11588.
10. Y. Aoyama, M. Asakawa, A. Yamagishi, H. Toi and H. Ogoshi, J. Am. Chem. Soc., 1990, 112, 3145; A. Galán, D. Andreu, A. M. Echavarren, P. Prados and J. de Mendoza, J. Am. Chem. Soc., 1992, 114, 1511.
11. Y. Aoyama, M. Asakawa, A. Yamagishi, H. Toi and H. Ogoshi, J. Am. Chem. Soc., 1990, 112, 3145; A. Galán, D. Andreu, A. M. Echavarren, P. Prados and J. de Mendoza, J. Am. Chem. Soc., 1992, 114, 1511.
12. G. R. Sullivan, D. Ciavarella and H. S. Mosher, J. Org. Chem., 1974, 39, 2411; K. Kabuto and Y. Sasaki, J. Chem. Soc., Chem. Commun., 1987, 670.
13. G. R. Sullivan, D. Ciavarella and H. S. Mosher, J. Org. Chem., 1974, 39, 2411; K. Kabuto and Y. Sasaki, J. Chem. Soc., Chem. Commun., 1987, 670.
14. H. Tsukube, H. Shiba and J. Uenishi, J. Chem. Soc., Dalton Trans., 1995, 181.
15. The interaction between anionic lanthanide complexes and cationic species has been demonstrated: R. L. Bassfield, J. Am. Chem. Soc., 1983, 105, 4168; I. Willner, Y. Eichen, S. Susan and B. Shoham, New J. Chem., 1991, 15, 879.
16. The interaction between anionic lanthanide complexes and cationic species has been demonstrated: R. L. Bassfield, J. Am. Chem. Soc., 1983, 105, 4168; I. Willner, Y. Eichen, S. Susan and B. Shoham, New J. Chem., 1991, 15, 879.
17. Y. Okada, Y. Kasai and J. Nishimura, Tetrahedron Lett., 1995, 36, 555.
18. G. Impellizzeri, G. Maccarrone, E. Rizzarelli, G. Vecchio, R. Corradini and R. Marchelli, Angew. Chem., Int. Ed. Engl., 1991, 30, 1348.
19. Macrocyclic polyamides exhibited perfect enantioselectivity for N-acetyl-amino acid amides, though they are not applicable to the extraction of zwitterionic amino acids: S. S. Yoon and W. C. Still, J. Am. Chem. Soc., 1993, 115, 823.