Chiral recognition and separation of β2-amino acids using non-covalently molecularly imprinted polymers

Analyst

Volumn 129, Issue 12, 2004, Pages 1211-1215

  Shim, Yong Ho ^a   Yilmaz, Ecevit ^b,d   Lavielle, Solange ^a   Haupt, Karsten ^c  

^a SORBONNE UNIVERSITÉ   (France)

^b LUND UNIVERSITY   (Sweden)

^c UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

^d Ideon Science Park   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

4 VINYLPYRIDINE; AMINO ACID DERIVATIVE; BENZYLOXYCARBONYL ALPHA AMINO ACID; BETA AMINO ACID; CARBONYL DERIVATIVE; ETHYLENE GLYCOL DIMETHACRYLATE; METHACRYLIC ACID; N (2 CHLOROBENZYLOXYCARBONYL) BETA 2 HOMOPHENYLALANINE; N (9 FLUORENYLMETHYLOXYCARBONYL) BETA 2 HOMOPHENYLALANINE; N BENZYLOXYCARBONYL BETA 2 HOMOPHENYLALANINE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COVALENT BOND; CROSS LINKING; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMERIZATION; RACEMIC MIXTURE; SYNTHESIS;

EID: 11944260598     PISSN: 00032654     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409836f     Document Type: Article

References (37)

1. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913-941; M. Werder, H. Hauser, S. Abele and D. Seebach, Helv. Chim. Acta, 1999, 82, 1774-1783; J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber and D. Seebach, ChemBioChem, 2001, 2, 445-455; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Helv. Chim. Acta, 2001, 84, 3503-3510; K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, J. Med. Chem., 2001, 44, 2460-2468.
2. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913-941; M. Werder, H. Hauser, S. Abele and D. Seebach, Helv. Chim. Acta, 1999, 82, 1774-1783; J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber and D. Seebach, ChemBioChem, 2001, 2, 445-455; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Helv. Chim. Acta, 2001, 84, 3503-3510; K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, J. Med. Chem., 2001, 44, 2460-2468.
3. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913-941; M. Werder, H. Hauser, S. Abele and D. Seebach, Helv. Chim. Acta, 1999, 82, 1774-1783; J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber and D. Seebach, ChemBioChem, 2001, 2, 445-455; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Helv. Chim. Acta, 2001, 84, 3503-3510; K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, J. Med. Chem., 2001, 44, 2460-2468.
4. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913-941; M. Werder, H. Hauser, S. Abele and D. Seebach, Helv. Chim. Acta, 1999, 82, 1774-1783; J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber and D. Seebach, ChemBioChem, 2001, 2, 445-455; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Helv. Chim. Acta, 2001, 84, 3503-3510; K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, J. Med. Chem., 2001, 44, 2460-2468.
5. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel and H. Widmer, Helv. Chim. Acta, 1996, 79, 913-941; M. Werder, H. Hauser, S. Abele and D. Seebach, Helv. Chim. Acta, 1999, 82, 1774-1783; J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber and D. Seebach, ChemBioChem, 2001, 2, 445-455; D. Seebach, M. Rueping, P. I. Arvidsson, T. Kimmerlin, P. Micuch, C. Noti, D. Langenegger and D. Hoyer, Helv. Chim. Acta, 2001, 84, 3503-3510; K. Gademann, T. Kimmerlin, D. Hoyer and D. Seebach, J. Med. Chem., 2001, 44, 2460-2468.
6. J. Lynas and B. Walker, Biochem. J., 1997, 325, 609-616.
7. D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz and H. Widmer, Helv. Chim. Acta. 1996, 79, 2043-2066; D. Seebach, J. V. Schreiber, P. I. Arvidsson and J. Frackenpohl, Helv. Chim. Acta, 2001, 84, 271-279; M. Rueping, J. V. Schreiber, G. Lelais, B. Jaun and D. Seebach, Helv. Chim. Acta, 2002, 85, 2577-2593.
8. D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz and H. Widmer, Helv. Chim. Acta. 1996, 79, 2043-2066; D. Seebach, J. V. Schreiber, P. I. Arvidsson and J. Frackenpohl, Helv. Chim. Acta, 2001, 84, 271-279; M. Rueping, J. V. Schreiber, G. Lelais, B. Jaun and D. Seebach, Helv. Chim. Acta, 2002, 85, 2577-2593.
9. D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz and H. Widmer, Helv. Chim. Acta. 1996, 79, 2043-2066; D. Seebach, J. V. Schreiber, P. I. Arvidsson and J. Frackenpohl, Helv. Chim. Acta, 2001, 84, 271-279; M. Rueping, J. V. Schreiber, G. Lelais, B. Jaun and D. Seebach, Helv. Chim. Acta, 2002, 85, 2577-2593.
10. Y.-D. Wu. J.-Q. Lin and Y.-L. Zhao, Helv. Chim. Acta, 2002, 85, 3144-3160.
11. D. C. Cole, Tetrahedron, 1994, 50, 9517-9582.
12. G. Cardillo and C. Tomasini, Chem. Soc. Rev., 1996, 117-128.
13. F. Felluga, P. Giuliana, M. Prodan, S. Priel, M. Visintin and E. Valentin, Tetrahedron Asym., 2001, 12, 3241-3249.
14. G. Guichard, S. Abele and D. Seebach, Helv. Chim. Acta, 1998, 81, 187-206; P. Micuch and D. Seebach, Helv. Chim. Acta, 2002, 85, 1567-1577.
15. G. Guichard, S. Abele and D. Seebach, Helv. Chim. Acta, 1998, 81, 187-206; P. Micuch and D. Seebach, Helv. Chim. Acta, 2002, 85, 1567-1577.
16. M. Liu and M. P. Sibi, Tetrahedron, 2002, 58, 7991-8035.
17. R. Ponsinet, G. Chassaing, J. Vaissermann and S. Lavielle, Eur. J. Org. Chem., 2000, 83-90.
18. E. Arvanitis, H. Ernst, A. A. Ludwig, A. J. Robinson and P. B. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1998, 3, 521-528.
19. H.-S. Lee, J.-S. Park, B. M. Kim and S. H. Gellman, J. Org. Chem., 2003, 68, 1575-1578.
20. (a) V. Piette, M. Lämmerhofer, W. Lindner and J. Crommen, J. Chromatogr. A, 2003, 987, 421-427;
21. (b) W. R. Oberleitner, N. M. Maier and W. Lindner, J. Chromatogr. A, 2002, 960, 97-108;
22. (c) M. Lämmerhofer and W. Lindner, J. Chromatogr. A, 1996, 741, 33-48.
23. A. Péter, L. Lázár, F. Fülöp and D. W. Armstrong, J. Chromatogr. A, 2001, 926, 229-238; A. Péter, J. Chromatogr. A, 2002, 955, 141-500.
24. A. Péter, L. Lázár, F. Fülöp and D. W. Armstrong, J. Chromatogr. A, 2001, 926, 229-238; A. Péter, J. Chromatogr. A, 2002, 955, 141-500.
25. M. Kempe, L. Fischer and K. Mosbach, J. Mol. Recog., 1993, 6, 25-29; M. Kempe and K. Mosbach, J. Chromatogr. A, 1995, 694, 3-13: K. Mosbach and O. Ramström, Bio/Technology, 1996, 14, 163-170; K. Haupt and K. Mosbach, Chem. Rev., 2000, 100, 2495-2504; K. Haupt and A. Fradet, L'actualité Chimique, 2001, 23-32.
26. M. Kempe, L. Fischer and K. Mosbach, J. Mol. Recog., 1993, 6, 25-29; M. Kempe and K. Mosbach, J. Chromatogr. A, 1995, 694, 3-13: K. Mosbach and O. Ramström, Bio/Technology, 1996, 14, 163-170; K. Haupt and K. Mosbach, Chem. Rev., 2000, 100, 2495-2504; K. Haupt and A. Fradet, L'actualité Chimique, 2001, 23-32.
27. M. Kempe, L. Fischer and K. Mosbach, J. Mol. Recog., 1993, 6, 25-29; M. Kempe and K. Mosbach, J. Chromatogr. A, 1995, 694, 3-13: K. Mosbach and O. Ramström, Bio/Technology, 1996, 14, 163-170; K. Haupt and K. Mosbach, Chem. Rev., 2000, 100, 2495-2504; K. Haupt and A. Fradet, L'actualité Chimique, 2001, 23-32.
28. M. Kempe, L. Fischer and K. Mosbach, J. Mol. Recog., 1993, 6, 25-29; M. Kempe and K. Mosbach, J. Chromatogr. A, 1995, 694, 3-13: K. Mosbach and O. Ramström, Bio/Technology, 1996, 14, 163-170; K. Haupt and K. Mosbach, Chem. Rev., 2000, 100, 2495-2504; K. Haupt and A. Fradet, L'actualité Chimique, 2001, 23-32.
29. M. Kempe, L. Fischer and K. Mosbach, J. Mol. Recog., 1993, 6, 25-29; M. Kempe and K. Mosbach, J. Chromatogr. A, 1995, 694, 3-13: K. Mosbach and O. Ramström, Bio/Technology, 1996, 14, 163-170; K. Haupt and K. Mosbach, Chem. Rev., 2000, 100, 2495-2504; K. Haupt and A. Fradet, L'actualité Chimique, 2001, 23-32.
30. G. Wulff, Am. Chem. Soc. Symp. Ser., 1986, 308, 186-230 (and references cited therein).
31. R. Arshady and K. Mosbach, Macromol. Chem. Phys., 1981, 182, 687-692.
32. W. Oppolzer, R. Moretti and S. Thomi, Tetrahedron, 1987, 43, 6009-6010.
33. V. R. Meyer, Chromatographia, 1987, 24, 639-645.
34. K. Haupt, A. Dzgoev and K. Mosbach, Anal. Chem., 1998, 70, 628-631.
35. L. I. Andersson and K. Mosbach, J. Chromatogr., 1990, 516, 313-322.
36. O. Ramström, L. I. Andersson and K. Mosbach, J. Org. Chem., 1993, 58, 7562-7564.
37. M. Kempe, PhD Thesis, University of Lund, 1994, p 44.