Synthesis and amino acid extraction abilities of chiral calix[4]arene triamides containing amino alcohol units

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 59, Issue 3-4, 2007, Pages 197-202

  Erdemir, Serkan ^a   Tabakci, Mustafa ^a   Yilmaz, Mustafa ^a  

^a SELCUK UNIVERSITY   (Turkey)

Author keywords

Amino acids; Calix 4 arene; Liquid liquid extraction; Triamide

Indexed keywords

EID: 36048992769     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-007-9336-x     Document Type: Article

References (46)

1. For general references on calixarenes, see: (a) Gutsche, C.D.: In: Stoddart, J.F. (ed.) Calixarenes Revisited, Monographs in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge, UK (1998)
2. (b) Mandolini, L., Ungaro, R. (eds.) Calixarenes in Action, Imperial College Press, London (2000)
3. (c) Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.) Calixarenes 2001, Kluwer, Dordrecht (2001)
4. (a) Böhmer, V.: CalIxarenes, Macrocycles wIth (almost) unlimited possibilities. Angew. Chem. 34, 713-745 (1995)
5. (b) Arnaud-Neu, F., Schwing-Weill, M.-J.: Calixarenes, new selective molecular receptors. Synthetic Metals 90, 157-164 (1997).
6. (c) Ludwig, R.: Calixarenes in analytical and separation chemistry. Fresenius J. Anal. Chem. 367, 103-128 (2000)
7. (d) Rebek, J. Jr.: Host-guest chemistry of calixarene capsules. J. Chem. Soc. Chem. Commun. 637-643 (2000)
8. (e) Moyer, B.A.: In: Gokel, G.W. (ed.) Molecular Recognition: Receptors for Cationic Guests. Comprehensive Supramolecular Chemistry, vol. 1, p. 377, Pergamon Press, New York, Oxford (1996)
9. Casnati, A., Sansone, F., Ungaro, R.: Peptido- and Glycocalixarenes: Playing with Hydrogen Bonds around Hydrophobic Cavities. Acc. Chem. Res. 36, 246-254 (2003)
10. Fulton, D.A., Stoddart, F.: Neoglycoconjugates Based on Cyclodextrins and Calixarenes. Bioconjugate Chem. 12, 655-672 (2001)
11. Hartley, J.H., James, T.D., Ward, C.J.: Synthetic receptors. J. Chem. Soc. Perkin Trans. 1 19, 3155-3184 (2000)
12. (a) Crossley, R.: Chirality and the Biological Activity of Drugs. CRC, New York (1995)
13. (b) Blaschke, G., Kraft, H.P., Fickentscher, K., Kohler, F.: Arzeneim-Forsch. 29, 1640 (1979)
14. For a general review on chiral calixarenes, see: Vysotsky, M.O., Schmidt, C., Böhmer, V.: In: Gokel, G. (ed.) Advances in Supramolecular Chemistry, vol. 7, pp. 139, Jai Press, Stanford (2000)
15. (a) Iwamoto, K., Shimizu, M., Araki, K., Shinkai, S.: Correction.Synthesis and Optical Resolution of Calix[4]arenes with Molecular Asymmetry. Systematic Classificaton of All Possible Chiral Isomers Derivable from Calix[4]arene. J. Am. Chem. Soc. 115, 12228 (1993)
16. (b) Ferguson, G., Gallagher, J.F., Giunta, L., Neri, P., Pappalardo, S., Parisi, M.J.: Synthetic strategies to inherently chiral calix[4]arenes with mixed ligating functionalities at the lower rim. Org. Chem. 59, 42-53 (1994)
17. (c) Böhmer, V., Kraft, D., Tabatabai, M.: Inherently chiral calixarenes. J. Incl. Phenom. 19, 17-39 (1994), and references cited therein.
18. For recent examples of preparative-scale optical resolution of inherently chiral calixarenes, see: (a) Cao, Y.D., Luo, J., Zheng, Q.Y., Chen, C.F., Wang, M.X., Huang, Z.T.: Preparation of Both Antipodes of Enantiopure Inherently Chiral Calix[4]crowns. J. Org. Chem. 69, 206-208 (2004)
19. (b) Narumi, F., Hattori, T., Yamabuki, W., Kabuto, C., Kameyama, H.: Resolution of inherently chiral anti-O,O'-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods. Tetrahedron: Asymmetry 16, 793-800 (2005)
20. (c) Li, S.Y., Zheng, Q.Y., Chen, C.F., Huang, Z.T.: Preparation of enantiopure inherently chiral calix[5]arenes. Tetrahedron: Asymmetry 16, 641-645 (2005)
21. (a) Okada, Y., Kasai, Y., Nishimura, J.: The selective extraction and transport of amino acids by calix[4]arene-derived esters. Tetrahedron Lett. 36, 555-558 (1995)
22. (b) Sansone, F., Barboso, S., Casnati, A., Fabbi, M., Pochini, A., Ugozzoli, F., Ungaro R.: Synthesis and Structure of Chiral Cone Calix[4]arenes Functionalized at the Upper Rim with L-Alanine Units. Eur. J. Org. Chem. 897-905 (1998)
23. (c) Xu, X., He, J., Chan, A.S.C., Han, X., Cheng, J.-P.: New chiral macrocyclic ligands. Design and synthesis of (R)-cysteine-containing calix[4]arenes. Tetrahedron: Asymmetry 10, 2685-2689 (1999)
24. (a) Sansone, F., Baldini, L., Casnati, A., Chierici, E., Faimani, G., Ugozzoli, F., Ungaro, R.: Chiral Dimeric Capsules from N, C-Linked Peptidocalix[4]arenes Self-Assembled through an Antiparallel β-Sheetlike Motif. J. Am. Chem. Soc. 126, 6204-6205 (2004)
25. (b) Francese, S., Cozzolino, A., Caputo, I., Esposito, C., Martino, M., Gaeta, C., Troisi, F., Neri, P.: Transglutaminase surface recognition by peptidocalix[4]arene diversomers. Tetrahedron Lett. 46, 1611-1615 (2005)
26. Zheng, Y.S., Zhang, C.: Exceptional Chiral Recognition of Racemic Carboxylic Acids by Calix[4]arenes Bearing Optically Pure α,β-Amino Alcohol Groups. Org. Lett. 6, 1189-1192 (2004)
27. (a) Meunier, S.J., Roy, R.: Polysialosides scaffolded on p-Tert-butylcalix[4]arene. Tetrahedron Lett. 37, 5469-5472 (1996)
28. (b) Dondoni, A., Marra, A., Scherrmann, M.-C., Casnati, A., Sansone, F., Ungaro, R.: Synthesis and Properties of O-Glycosyl Calix[4]Arenes (Calixsugars). Chem. Eur. J. 3, 1774-1782 (1997)
29. Yuan, H.-S., Huang, Z.-T.: Synthesis of chiral calix[4]arenes bearing tartaric ester moieties. Tetrahedron: Asymmetry 10, 429-437 (1999)
30. (a) Kubo, Y., Maeda, S., Tokite, S., Kubo, M.: Colorimetric chiral recognition by a molecular sensor. Nature 382, 522-524 (1996)
31. (b) Pinkhassik, E., Stibor, I., Casnati, A., Ungaro, R.: Synthesis of Upper and Lower Rim Binaphthyl Bridged Calix[4]arenes: New Potential Chiral Hosts for Molecular Recognition and Catalysis. J. Org. Chem. 62, 8654 (1997)
32. Neri, P., Bottino, A., Geraci, C., Piattelli, M.: Synthesis of glycidyl calixarenes, versatile substrates for the preparation of chiral calixarene-based ligands. Tetrahedron: Asymmetry 7, 17-20 (1996)
33. Soi, A., Pfeiffer, J., Jauch, J., Schurig, V.: Synthesis of chiral calix[n]arenes. Part 2: Synthesis of new chiral calix[n]arenes based on (p-hydroxy-phenyl)-menthone. Tetrahedron: Asymmetry 12, 177-182 (1999)
34. Liu, F., Lu, G.-Y., He, W.-J., Liu, M.-H., Zhu, L.-G.: Enantioselective Recognition Of Calix[4]Arene Derivatives Bearing Chiral Bicyclic Guanidinium For D/L-Phenylalanine Zwitterions At The Air-Water Interface. Thin Solid Films 468, 244-249 (2004)
35. (a) Tabakci, M., Tabakci, B., Yilmaz, M.: Design and Synthesis of New Chiral Calix[4]arenes as Liquid Phase Extraction Agents for α-Amino Acid Methylesters and Chiral α-Amines. J. Incl. Phenom. Macrocycl. Chem. 53, 51-56 (2005)
36. (b) Erdemir, S., Tabakci, M., Yilmaz, M.: Synthesis and chiral recognition abilities of new calix[6]arenes bearing amino alcohol moieties. Tetrahedron: Asymmetry 17, 1258-1263 (2006)
37. Gutsche, C.D., Iqbal, M.: p-tert-butylcalix[4]arene. Org. Synth. 68, 234-237 (1990)
38. Abidi, R., Oueslati, I., Amri, H., Thuery, P., Nierlich, M., Asfari, Z., Vicens, J.: Synthesis, structure and complexing properties of new calix[4](aza)crowns. Tetrahedron Lett. 42, 1685-1689 (2001)
39. (a) Wu, Y., Shen, X., Duan, C., Liu, Y., Xu, Z.: New double-1,2-amide- bridged calix[4]arenes by aminolysis of calix[4]arene esters. Tetrahedron Lett. 40, 5749-5752 (1999)
40. (b) Wu, Y., Liu, H., Liu, Y., Duan, C., Hu, J., Xu, Z.: A Facile Method of Synthesis of a Calix[4]arene Amide and the Crystal Structure of a Self-assembled Calix[4]arene Amide via van Der Waals Interaction. J. Incl. Phenom. Macrocycl. Chem. 36, 473-478 (2000)
41. Bozkurt, S., Karakucuk, A., Sirit, A., Yilmaz, M.: Synthesis of two calix[4]arene diamide derivatives for extraction of chromium(VI). Tetrahedron 61, 10443-10448 (2005)
42. Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M.: Synthesis and Extraction Studies of a Versatile Calix[4]arene-Based "Proton-Switchable Extractant" for Toxic Metals and Dichromate Anions. J. Incl. Phenom. Macrocycl. Chem. 45, 267-270 (2003)
43. Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D.M., Yilmaz, M.: Polyme Supported Calix[4]Arene Derivatives for the Extraction of Metals and Dichromate Anions. J. Polym. Environ. 11, 67-74 (2003)
44. Tabakci, M., Ersoz, M., Yilmaz, M.: A Calix[4]arene-Containing Polysiloxane Resin for Removal of Heavy Metals and Dichromate Anion. J. Macromol. Sci. Pure Appl. Chem. 43, 57-69 (2006)
45. Garrier, E., le Gac, S., Jabin, I.: First enantiopure calix[6]aza-cryptand: synthesis and chiral recognition properties towards neutral molecules. Tetrahedron: Asymmetry 16, 3767-3771 (2005)
46. Pedersen, C.J.: Ionic complexes of macrocyclic polyethers. J. Fed. Proc. Fed. Am. Soc. Exp. Biol. 27, 1305-1309 (1968)