Chiral cyclohexane based fluorescent chemosensors for enantiomeric discrimination of aspartate

Tetrahedron

Volumn 64, Issue 14, 2008, Pages 3217-3224

  Costero, Ana M ^a   Colera, Manuel ^a   Gaviña, Pablo ^a   Gil, Salvador ^a   Kubinyi, Miklós ^b,c   Pál, Krisztina ^b   Kállay, Mihály ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; CYCLOHEXANE; DICARBOXYLIC ACID; GLUTAMIC ACID; TARTARIC ACID; TETRAMETHYLAMMONIUM;

ARTICLE; BIOSENSOR; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; ENANTIOMER; FLUORESCENCE; PRIORITY JOURNAL; SENSOR; STOICHIOMETRY; SYNTHESIS;

EID: 39649096055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.085     Document Type: Article

References (37)

1. Fabbrizzi L., Licchelli M., and Labaioli G. Coord. Chem. Rev. 205 (2000) 85-108
2. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419-4476
3. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
4. Gale P.A., García-Garrido S.E., and Garric J. Chem. Soc. Rev. 37 (2008) 151-190
5. Suksai C., and Tuntulani T. Chem. Soc. Rev. 32 (2003) 192-202
6. James T.D., Samankumara Sandanayake K.R.A., and Shinkai S. Nature 374 (1996) 345-347
7. Kubo Y., Maeda S., Tokita S., and Kubo M. Nature 382 (1996) 522-524
8. Naemura K., Tobe Y., and Kaneda T. Coord. Chem. Rev. 148 (1996) 199-219
9. Zhang X.X., Bradshaw J.S., and Izatt R.M. Chem. Rev. 97 (1997) 3313-3361
10. Webb T.H., and Wicox C.S. Chem. Soc. Rev. 22 (1993) 383-395
11. Finn M.G. Chirality 14 (2002) 534-540
12. See for example:.
13. Ragusa A., Rossi S., Hayes J.M., Stein M., and Kilburn J.D. Chem.-Eur. J. 11 (2005) 5674-5688
14. Rossi S., Kyne G.M., Turner D.L., Wells N.J., and Kilburn J.D. Angew. Chem., Int. Ed. 41 (2002) 4233-4236
15. Lee C.-S., Teng P.-F., Wong W.-L., Kwong H.-L., and Chan A.S.C. Tetrahedron 61 (2005) 7924-7930
16. Alfonso I., Dietrich B., Rebolledo F., Gotor V., and Lehn J.-M. Helv. Chim. Acta 84 (2001) 280-295
17. Folmer A.J., Frantz L., Vincent M., and Anslyn E.V. J. Am. Chem. Soc. 127 (2005) 7986-7987
18. Tsubaki K., Tanima D., Nuruzzaman M., Kusumoto T., Fuji K., and Kawabata T. J. Org. Chem. 70 (2005) 4609-4616
19. Pagliari S., Corradini R., Galaverna G., Sforza S., Dossena A., Montalti M., Prodi L., Zaccheroni N., and Marchelli R. Chem.-Eur. J. 10 (2004) 2749-2758
20. Wong W.-L., Huang K.-H., Teng P.-F., Lee C.-S., and Kwong H.-L. Chem. Commun. (2004) 384-385
21. De Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., Mc Coy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515-1566
22. Nishizawa S., Kaneda H., Uchida T., and Teramae N. J. Chem. Soc., Perkin Trans. 2 (1998) 2325-2328
23. Nishizawa S., Kaneda H., Kato Y., and Teramae N. J. Am. Chem. Soc. 121 (1999) 9463-9464
24. Samoshin V.V. Mini-Rev. Org. Chem. 2 (2005) 225-235
25. Amendola V., Boiocchi M., Esteban-Gómez D., Fabrizzi L., and Monzani E. Org. Biomol. Chem. 3 (2005) 2632-2639
26. Costero A.M., Colera M., Gaviña P., and Gil S. Chem. Commun. (2006) 761-763
27. Costero A.M., Villarroya J.P., Gil S., Aurell M.J., and Ramirez de Arellano M.C. Tetrahedron 58 (2002) 6729-6734
28. Chandrasekar M., Sekar G., and Singh V.K. Tetrahedron Lett. 41 (2000) 10079-10089
29. Berova N., and Nakanishi N. In: Berova N., Nakanishi N., and Woody R.W. (Eds). Circular Dichroism: Principles and Applications. 2nd ed. (2000), Wiley-VCH, New York, NY 337-382
30. Kwit M., and Gawronski J. Tetrahedron 59 (2003) 9323-9331
31. Boiadjiev S.E., and Lightner D.A. Chirality 17 (2005) 316-322
32. The spectrum was calculated by ZINDO/S method (. Hanson L.K., Fajer J., Thompson M.A., and Zerner M.C. J. Am. Chem. Soc. 109 (1987) 4728-4730 )
33. using Gaussian 03 program package (. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.01 (2003), Gaussian, Pittsburgh, PA )
34. Rubio M., Merchan M., Orti E., and Roos B.O. Chem. Phys. 179 (1994) 395-409
35. Halgren (. J. Comput. Chem. 17 (1996) 490-519 ) and simulated annealing algorithm were used.
36. They were carried out by Spartan'02 package (. Spartan'02 (2002), Wavefunction, Irvine, CA, USA )
37. SPECFIT/32TM GLOBAL ANALYSIS SYSTEM v.3.0 (2000), Spectrum Software Associates, Marlborough, MA, USA. www.bio-logic.info/rapid-kinetics/specfit.html