N-linked peptidocalix[4]arene bisureas as enantioselective receptors for amino acid derivatives

Journal of Organic Chemistry

Volumn 72, Issue 9, 2007, Pages 3223-3231

  Yakovenko, Anton V ^a   Boyko, Vyacheslav I ^a   Kalchenko, Vitaly I ^a   Baldini, Laura ^b,c   Casnati, Alessandro ^b,c   Sansone, Francesco ^b,c   Ungaro, Rocco ^b,c  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^b UNIVERSITY OF PARMA   (Italy)

^c INSTM   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ABILITY; CONFORMATIONAL PROPERTIES; ISOCYANATE; METHYL ESTERS;

AMINO ACIDS; CARBOXYLIC ACIDS; CONFORMATIONS; DERIVATIVES; ENANTIOSELECTIVITY; LIGANDS; MOLECULAR MODELING;

UREA;

ALANINE; AMINO ACID DERIVATIVE; CALIXARENE; GLYCINE; ISOCYANATE; ISOLEUCINE; N ACETYLPHENYLALANINE; PEPTIDOCALIX[4]ARENE DERIVATIVE; PHENOL DERIVATIVE; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

AMINO ACID ANALYSIS; ARTICLE; BINDING AFFINITY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMINO ACIDS; ANIONS; BINDING SITES; CALIXARENES; CHEMISTRY, ORGANIC; HYDROGEN; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PHENOLS; PHENYLALANINE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; UREA;

EID: 34247580691     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062410x     Document Type: Article

References (40)

1. Kubik, S.; Reyheller, C.; Stuwe, S. J. Inclusion Phenom. Macrocyclic Chem. 2005, 52, 137-187.
2. Miller, C. Nature 2006, 440, 484-489.
3. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 487-516.
4. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221.
5. Anion Sensing; Stibor, I., Ed.; Topics in Current Chemistry 255; Springer: Berlin, 2005.
6. Meshcheryakov, D.; Böhmer, V.; Bolte, M.; Hubscher-Bruder, W.; Arnaud-Neu, F.; Herschbach, H.; Van Dorsselaer, A.; Thondorf, I.; Mogelin, W. Angew. Chem., Int. Ed. 2006, 45, 1648-1652.
7. Stibor, I.; Zlatuskova, P. Chiral Recognition of Anions. In Anion Sensing; Stibor, I., Ed.; Topics in Current Chemistry 255; Springer: Berlin, 2005; pp 31-63.
8. Casnati, A.; Sansone, F.; Ungaro, R. Calixarene Receptors in Ion Recognition and Sensing. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; Cerberus Press Inc.: South Miami, 2004; Vol. 9, pp 165-218.
9. Lhotak, P. Anion receptors based on calixarenes. In Anion Sensing; Stibor, I., Ed.; Topics in Current Chemistry 255; Springer: Berlin, 2005; pp 65-95.
10. Vysotsky, M.; Schmidt, C.; Bohmer, V. Chirality in Calixarenes and Calixarene Assemblies. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press: Greenwich, CT, 2000; Vol. 7, pp 139-233.
11. Ludwig, R. Microchim. Acta 2005, 152, 1-19.
12. Grady, T.; Harris, S. J.; Smyth, M. R.; Diamond, D.; Hailey, P. Anal. Chem. 1996, 68, 3775-3782.
13. Pinkhassik, E.; Stibor, I.; Casnati, A.; Ungaro, R. J. Org. Chem. 1997, 62, 8654-8659.
14. Zheng, Y. S.; Zhang, C. Org. Lett. 2004, 6, 1189-1192.
15. Erdemir, S.; Tabakci, M.; Yilmaz, M. Tetrahedron: Asymmetry 2006, 17, 1258-1263.
16. Kocabas, E.; Karakucuk, A.; Sirit, A.; Yilmaz, M. Tetrahedron: Asymmetry 2006, 17, 1514-1520.
17. Karakucuk, A.; Durmaz, M. S. A.; Yilmaz, M.; Demirel, A. Tetrahedron: Asymmetry 2006, 17, 1963-1968.
18. Sansone, F.; Baldini, L.; Casnati, A.; Lazzarotto, M.; Ugozzoli, F.; Ungaro, R. Proc Natl. Acad. Sci. U.S.A. 2002, 99, 4842-4847.
19. Qing, G. Y.; He, Y. B.; Zhao, Y.; Hu, C. G.; Liu, S. Y.; Yang, X. Eur. J. Org. Chem. 2006, 1574-1580.
20. Casnati, A.; Sansone, F.; Ungaro, R. Acc. Chem. Res. 2003, 36, 246-254.
21. Bogdan, A.; Rudzevich, Y.; Vysotsky, M. O.; Bohmer, V. Chem. Commun. 2006, 2941-2952 and references therein.
22. Santoyo, G. F.; Torres, P. A.; Barria, C. S. Eur. J. Org. Chem. 2000, 3587-3593.
23. Sansone, F.; Chierici, E.; Casnati, A.; Ungaro, R. Org. Biomol. Chem. 2003, 1, 1802-1809.
24. van Wageningen, A. M. A.; Snip, E.; Verboom, W.; Reinhoudt, D. N.; Boerrigter, H. Liebigs Ann./Recl. 1997, 2235-2245.
25. Boyko, V. I.; Yakovenko, A. V.; Tsymbal, I. F.; Kalchenko, V. I. Mendeleev Commun. 2006, 24-26.
26. Cobben, P. L. H. M.; Egberink, R. J. M.; Bomer, J. G.; Bergveld, P.; Verboom, W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1992, 114, 10573-10582.
27. Bitter, I.; Grun, A.; Toth, G.; Balazs, B.; Horvath, G.; Toke, L. Tetrahedron 1998, 54, 3857-3870.
28. Webber, P. R. A.; Cowley, A.; Drew, M. G. B.; Beer, P. D. Chem.-Eur. J. 2003, 9, 2439-2446.
29. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325-4342.
30. Rincon, A. M.; Prados, P.; de Mendoza, J. Eur. J. Org. Chem. 2002, 640-644.
31. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554.
32. Cierpicki, T.; Otlewski, J. J. Biomol. NMR 2001, 21, 249-261.
33. Although at low resolution, the X-ray crystal structure of a C-linked (N-tosylalaninamido)peptidocalix[4]arene, was recently reported (ref 38) and showed a similar H-bonding pattern of the amide chains.
34. Conners, K. A. Binding Constants; John Wiley & Sons: New York, 1987.
35. Frassineti, C.; Ghelli, S.; Gans, P.; Sabatini, A.; Moruzzi, M. S.; Vacca, A. Anal. Biochem. 1995, 231, 374-382.
36. Frassineti, C.; Alderighi, L.; Gans, P.; Sabatini, A.; Vacca, A.; Ghelli, S. Anal. Bioanal. Chem. 2003, 376, 1041-1052.
37. Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820.
38. Ben Sdira, S.; Felix, C. P.; Giudicelli, M. B. A.; Seigle-Ferrand, P. F.; Perrin, M.; Lamartine, R. J. J. Org. Chem. 2003, 68, 6632-6638.
39. Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. Determination of stability constants [in supramolecular chemistry]. In Comprehensive Supramolecular Chemistry, 8th ed.; Davies, J. E. D., Ripmeester, J. A., Eds.; Elsevier: Oxford, 1996; pp 425-482.
40. SPARTAN 04, release 1.01: Wavefunction, Inc.: Irvine, CA, 2004; http://www.wavefun.com.