Efficient and selective transport of ω-amino acids across a bulk chloroform membrane by a macrocyclic dicopper(II) complex

Tetrahedron Letters

Volumn 45, Issue 8, 2004, Pages 1643-1646

  Pichler, Umberto ^a   Scrimin, Paolo ^a   Tecilla, Paolo ^b   Tonellato, Umberto ^a   Veronese, Andrea ^a   Verzini, Massimo ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Amino acid transport; Copper(II); Macrocyclic receptor; Molecular recognition; Supramolecular chemistry

Indexed keywords

CHLOROFORM; COPPER COMPLEX; LIGAND; MACROCYCLIC COMPOUND; OMEGA AMINO ACID;

AMINO ACID TRANSPORT; ARTICLE; BINDING AFFINITY; LIPOPHILICITY; MEMBRANE TRANSPORT; TRANSPORT KINETICS;

EID: 0842283443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.125     Document Type: Article

References (38)

1. For an overview see: Roberts S.M. Molecular Recognition, Chemical and Biochemical Problems. 1989;The Royal Society of Chemistry, London.
2. For an excellent collection of reviews on molecular recognition see: Atwood J.L., Davies J.E.D., Macnicol D.D., Vögtle F. Comprehensive Supramolecular Chemistry. 1996;Elsevier, Exeter.
3. Also see: Lehn J.-M. Supramolecular Chemistry. 1995;VCH, Weinheim.
4. Schneider H.-J., Yatsimirsky A. Principles and Methods in Supramolecular Chemistry. 2000;Wiley, Chichester.
5. Tabushi I., Kuroda Y., Mizutani T. J. Am. Chem. Soc. 108:1986;4514-4518.
6. Aoyama Y., Asakawa M., Yamagishi A., Toi H., Ogoshi H. J. Am. Chem. Soc. 112:1990;3145-3151.
7. Galàn A., Andreu D., Echavarren A.M., Prados P., de Mendoza J. J. Am. Chem. Soc. 114:1992;1511-1512.
8. Corradini R., Dossena A., Impellizzeri G., Maccarrone G., Marchelli R., Rizzarelli E., Sartor G., Vecchio G. J. Am. Chem. Soc. 116:1994;10267-10274.
9. Metzger A., Gloe K., Stephan H., Schmidtchen F.P. J. Org. Chem. 61:1996;2051-2055.
10. Chen H.C., Ogo S., Fish R.H. J. Am. Chem. Soc. 118:1996;4993-5001.
11. Tsukube H., Uenishi J., Kanatani T., Itoh H., Yonemitsu O. Chem. Commun. 1996;477-478.
12. Chin J., Lee S.S., Lee K.J., Park S., Kim D.H. Nature. 401:1999;254-257.
13. Sasaki S., Hashizume A., Citterio D., Fujii E., Suzuki K. Tetrahedron Lett. 43:2002;7243-7245.
14. Hortala M.A., Fabbrizzi L., Marcotte N., Stomeo F., Taglietti A. J. Am. Chem. Soc. 125:2003;20-21.
15. Gao J., Martell A.E., Reibenspies J. Helv. Chim. Acta. 86:2003;196-203.
16. Ballistreri F.P., Notti A., Pappalardo S., Parisi M.F., Pisagatti I. Org. Lett. 5:2003;1071-1074.
17. Hernandez J.V., Muniz F.M., Oliva A.I., Simon L., Perez E., Moran J.R. Tetrahedron Lett. 44:2003;6983-6985.
18. Sunamoto J., Iwamoto K., Mohri Y., Kominato T. J. Am. Chem. Soc. 104:1982;5502-5504.
19. Rebek J. Jr., Askew B., Nemeth D., Parris K. J. Am. Chem. Soc. 109:1987;2432-2434.
20. Reetz M.T., Huff J., Rudolph J., Töllner K., Deege A., Goddard R. J. Am. Chem. Soc. 116:1994;11588-11589.
21. Scrimin P., Tecilla P., Tonellato U. Tetrahedron. 51:1995;217-230.
22. Sessler J.L., Andrievsky A. Chem. Eur. J. 4:1998;159-167.
23. Pietraszkiewicz M., Kozbial M., Pietraszkiewicz O. J. Membr. Sci. 138:1998;109-113.
24. Tsukube H., Shinoda S., Uenishi J., Kanatani T., Itoh H., Shiode M., Iwachido T., Yonemitsu O. Inorg. Chem. 37:1998;1585-1591.
25. Barboiu M., Hovnanian N.D., Luca C., Cot L. Tetrahedron. 55:1999;9221-9232.
26. Breccia P., Van Gool M., Perez-Fernandez R., Martin-Santamaria S., Gago F., Prados P., de Mendoza J. J. Am. Chem. Soc. 125:2003;8270-8284.
27. Scrimin P., Tecilla P., Tonellato U. Eur. J. Org. Chem. 1:1998;1143-1153.
28. Bertoncin F., Mancin F., Scrimin P., Tecilla P., Tonellato U. Langmuir. 14:1998;975-978.
29. Tecilla P., Tonellato U., Veronese A., Felluga F., Scrimin P. J. Org. Chem. 62:1997;7621-7628.
30. Scrimin P., Tecilla P., Tonellato U., Valle G., Veronese A. J. Chem. Soc., Chem. Comm. 1995;1163-1164.
31. Scrimin P., Tecilla P., Tonellato U., Valle G., Veronese A. Tetrahedron. 51:1995;527-538.
32. 2: C, 79.49; H, 9.22; N, 8.18; Found: C, 79.02; H, 9.31, N, 8.09.
33. 3O: C, 79.00; H, 9.44; N, 8.37; Found: C, 78.72; H, 9.48, N, 8.26.
34. 2 complex). See: Arnaud-Neu F., Sanchez M., Schwing-Weill M.J. Helv. Chim. Acta. 68:1985;840-845.
35. 2. The tube was immersed in a thermostatic bath kept at 25°C. The stirring speed of the magnetic bar was >200 rpm. Above this value the rate of transport does not depend on the stirring speed.
36. In these experiments the metal ion is transported at a higher rate than the amino acids and this is probably related to the formation of a ternary complex comprising two ligands and two metal ions (or two ligand and one metal ion in the case of 2 ). This ternary complex is productive as a Cu(II) carrier but not as an amino acid carrier and competes with the ternary complex comprising ligand, copper and amino acid. This behaviour has already been observed. It has been ascribed to a lower affinity for the metal ion of the amino acid with respect to the ligand (see Ref. [4d]).
37. This is based on the rough assumption that the binding constant of the second Cu(II) ion by the macrocycle is the same as that of the first one. Quite likely it is lower (see Ref. 8) and, as a consequence, the transport efficiency of the macrocycle is underestimated.
38. The apparent binding constants of the carriers for the three amino acids were obtained by interpolation of the rate of transport as a function of carrier concentration (see Fig. 2 for 1 and β-Phe) plots by using a Michaelis-Menten-like equation. In the case of α- and γ-amino acids the curvature of the profiles was less defined than that of the β-analogue and, therefore, the error in the determination of the formation constant is probably higher. However, since we are considering ratios of constants the effect of the error is somehow minimized.