Multipoint molecular recognition of amino acids and biogenic amines by ureidocalix[5]arene receptors

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1071-1074

  Ballistreri, Francesco P ^a   Notti, Anna ^b   Pappalardo, Sebastiano ^a   Parisi, Melchiorre F ^b   Pisagatti, Ilenia ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BIOGENIC AMINE; CALIXARENE; AMINO ACID; QUATERNARY AMMONIUM DERIVATIVE; UREA;

ARTICLE; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHEMISTRY; MACROMOLECULE;

AMINO ACIDS; BINDING SITES; BIOGENIC AMINES; CALIXARENES; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; UREA;

EID: 0042730198     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034093b     Document Type: Article

References (34)

1. Tabor, W. C.; Tabor, H. Annu. Rev. Biochem. 1984, 53, 749-790.
2. Demello, M. C. F.; Guerrapeixe, R.; Demello, F. G. Neurochem. Int. 1993, 22, 249-253.
3. Perry, T. L.; Berry, K.; Diamond, S.; MoK, J. J. Neurochem. 1971, 18, 513-519. Fahn, S.; Côte, L. J. J. Neurochem. 1968, 15, 209-213.
4. Perry, T. L.; Berry, K.; Diamond, S.; MoK, J. J. Neurochem. 1971, 18, 513-519. Fahn, S.; Côte, L. J. J. Neurochem. 1968, 15, 209-213.
5. Moulinoux, J.-P.; Quemener, V.; Delcros, J.-G.; Cipolla, B. In Polyamines in cancer: Basic Mechanisms and Clinical Approaches; Nishioka, K., Ed.; Springer: New York, 1996; Chapter 10, pp 233-249.
6. Bartholomew, B. A.; Berry, P. R.; Rodhouse, J. C. Gilbert, R. J. Epidemiol. Infect. 1987, 99, 775-782.
7. Shalaby, A. R. Food Res. Int. 1996, 29, 675-690.
8. Khuhawar, M. Y.; Qureshi, G. A. J. Chromatogr. B 2001, 764, 385-407.
9. Arce, L.; Carretero, A. S.; Rios, A.; Cruces, C.; Fernandez, A.; Valcarcel, M. J. Chromatogr. A 1998, 816, 243-249.
10. Poels, I.; Nagels, L. J. Anal. Chim. Acta 2001, 440, 89-98.
11. Sansone, S.; Segura, M.; Ungaro, R. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic: Dordrecht, 2001; Chapter 27, pp 496-512.
12. Cadogan, F.; Nolan, K.; Diamond, D. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic: Dordrecht, 2001; Chapter 34, pp 627-641.
13. (a) Arnaud-Neu, F.; Fuangswasdi, S.; Notti, A.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 1998, 37, 112-114.
14. (b) Ferguson, G.; Notti, A.; Pappalardo, S.; Parisi, M. F.; Spek, A. L. Tetrahedron Lett. 1998, 39, 1965-1968.
15. (c) Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122-2126.
16. Giannetto, M.; Mori, G.; Notti, A.; Pappalardo, S.; Parisi, M. F. Anal. Chem. 1998, 70, 4631-4635.
17. For the molecular recognition of N-α-protected amino acid esters by a self-assembled cylindrical capsule, see: Hayashida, O.; Sebo, L.; Rebek, J., Jr. J. Org. Chem. 2002, 67, 8291-8298.
18. (a) Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
19. (b) Budka, J.; Lhoták, P.; Michlová, V.; Stibor, I. Tetrahedron Lett. 2001, 42, 1583-1586.
20. Arduini, A.; Secchi, A.; Pochini, A. J. Org. Chem. 2000, 65, 9085-9091.
21. Calix[4]-, calix[5]-, and calix[6]arenes with ureido functionalities at the upper rim have also been employed for the self-assembling of molecular capsules; see: Rebek, J., Jr. Chem. Commun. 2000, 637-643; Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem. Eur. J. 2001, 7, 4403-4410. Yanase, M.; Haino, T.; Fukazawa, Y. Tetrahedron Lett. 1999, 40, 2781-2784. Gonzáles, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini, A.; Pochini, A.; Prados, P.; de Mendoza, J. Chem. Eur. J. 2000, 6, 73-80.
22. Calix[4]-, calix[5]-, and calix[6]arenes with ureido functionalities at the upper rim have also been employed for the self-assembling of molecular capsules; see: Rebek, J., Jr. Chem. Commun. 2000, 637-643; Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem. Eur. J. 2001, 7, 4403-4410. Yanase, M.; Haino, T.; Fukazawa, Y. Tetrahedron Lett. 1999, 40, 2781-2784. Gonzáles, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini, A.; Pochini, A.; Prados, P.; de Mendoza, J. Chem. Eur. J. 2000, 6, 73-80.
23. Calix[4]-, calix[5]-, and calix[6]arenes with ureido functionalities at the upper rim have also been employed for the self-assembling of molecular capsules; see: Rebek, J., Jr. Chem. Commun. 2000, 637-643; Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem. Eur. J. 2001, 7, 4403-4410. Yanase, M.; Haino, T.; Fukazawa, Y. Tetrahedron Lett. 1999, 40, 2781-2784. Gonzáles, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini, A.; Pochini, A.; Prados, P.; de Mendoza, J. Chem. Eur. J. 2000, 6, 73-80.
24. Calix[4]-, calix[5]-, and calix[6]arenes with ureido functionalities at the upper rim have also been employed for the self-assembling of molecular capsules; see: Rebek, J., Jr. Chem. Commun. 2000, 637-643; Vysotsky, M. O.; Pop, A.; Broda, F.; Thondorf, I.; Böhmer, V. Chem. Eur. J. 2001, 7, 4403-4410. Yanase, M.; Haino, T.; Fukazawa, Y. Tetrahedron Lett. 1999, 40, 2781-2784. Gonzáles, J. J.; Ferdani, R.; Albertini, E.; Blasco, J. M.; Arduini, A.; Pochini, A.; Prados, P.; de Mendoza, J. Chem. Eur. J. 2000, 6, 73-80.
25. Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25, 839-842.
26. All new compounds were characterized by elemental analysis and NMR and MS spectroscopy.
27. Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586-601. De Salvo, G.; Gattuso, G.; Notti, A.; Parisi, M. F.; Pappalardo, S. J. Org. Chem. 2002, 67, 684-692.
28. Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586-601. De Salvo, G.; Gattuso, G.; Notti, A.; Parisi, M. F.; Pappalardo, S. J. Org. Chem. 2002, 67, 684-692.
29. 3OD to solubilize the dication and amino acid guests under study.
30. ∈-Ahx is a lysine analogue employed as plasminogen inhibitor, see: Markus, G. Fibrinolysis 1996, 10, 75-85.
31. +, respectively.
32. +⊂1a and ∈-Ahx⊂1a complexes.
33. 1H NMR, under the experimental conditions reported in Table 1.
34. -3 M) host-guest mixtures.