Design and synthesis of fluorescent β-cyclodextrins for the enantioselective sensing of α-amino acids

Chirality

Volumn 15, Issue SUPPL., 2003, Pages

  Corradini, R ^a   Paganuzzi, C ^a   Marchelli, Rosangela ^a   Pagliari, S ^a   Sforza, S ^a   Dossena, A ^a   Galaverna, G ^a   Duchateau, A ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b DSM RESEARCH   (Netherlands)

Author keywords

Chiral discrimination; Copper(II) complexes; Enantiomers; Fluorescent sensors; Ligand exchange

Indexed keywords

ALPHA AMINO ACID; AMIDE; AMINE; AMINO ACID AMIDE; BETA CYCLODEXTRIN DERIVATIVE; COPPER COMPLEX; CYCLOHEXYLGLYCINE; DANSYL CHLORIDE; HYDROXYACID; N ACETYLAMINO ACID; N CARBAMOYLAMINO ACID; N METHYLAMINO ACID; PHENYLALANINE; PHENYLGLYCINE; PROLINE; SULFONAMIDE; UNCLASSIFIED DRUG; VALINE;

CHEMOSENSOR; CHIRALITY; COMPLEX FORMATION; CONFERENCE PAPER; DIASTEREOISOMER; ENANTIOSELECTIVITY; FLUORESCENCE SPECTROSCOPY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SENSOR; SYNTHESIS;

AMINO ACIDS; BETA-CYCLODEXTRINS; CYCLODEXTRINS; FLUORESCENT DYES; GLYCINE; LIGANDS; MODELS, CHEMICAL; PHENYLALANINE; PROLINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 0042164780     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10272     Document Type: Conference Paper

References (42)

1. Czarnik AW (ed.). Fluorescent chemosensors for ion and molecule recognition. ACS Symposium Series 538; Washington, DC: American Chemical Society; 1992.
2. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE. Signaling recognition events with fluorescent sensors and switches. Chem Rev 1997;97:1515-1566.
3. Prodi L, Bolletta F, Montalti M, Zaccheroni N. Recent developments in transition metal ion detection by luminescent chemosensors. Coord Chem Rev 2000;205:59-83.
4. Fabrizzi L, Poggi A. Sensors and switching from supramolecular chemistry. Chem Soc Rev 1995;24:197-202.
5. Grynkiewicz G, Poenie M, Tsien RY. A new generation of calcium indicators with greatly improved fluorescence properties. J Biol Chem 1985;260:3440-3450.
6. Czarnik AW. Chemical communication in water using fluorescent chemosensors. Acc Chem Res 1994;27:302-308, and references therein.
7. Charbonnière LJ, Ziessel R, Montalti M, Prodi L, Zaccheroni N, Boehme C, Wipff G. Luminescent lanthanide complexes of a bisbipyridine-phosphine-oxide ligand as tools for anion detection. J Am Chem Soc 2002;124:7779-7788.
8. Metzger A, Anslyn EV. A chemosensor for citrate in beverages. Angew Chem Int Ed Engl 1998;37:649-652.
9. Chen C, Wagner H, Still WC. Fluorescent, sequence-selective peptide detection by synthetic small molecules. Science 1998;279:851-853.
10. de Silva AP, Gunaratne HQN, McVeigh C, Maguire GEM, Maxwell PRS, O'Hanlon E. Fluorescent signalling of the brain neurotransmitter γ-aminobutyric acid and related amino acid zwitterions. Chem Commun 1996;2191.
11. James JD, Linnane P, Shinkai S. Fluorescent saccharide receptors: a sweet solution to the design, assembly and evaluation of boronic acid derived PET sensors. Chem Commun 1996:281-288.
12. Adams SR, Harootunian AT, Buechler YJ, Taylor SS, Tsien RY. Fluorescence ratio imaging of cyclic AMP in single cells. Nature 1991;349: 694-697.
13. Kahn K, De Biaso R, Taylor DL. Patterns of elevated free calcium and calmodulin activator in living cells. Nature 1992;359:736.
14. Yuste R, Peinado A, Katz LC. Neuronal domains in developing neocortex. Science 1992;257:665.
15. Wang D, Liu TJ, Zhang WC, Slaven IV WT, CJ Li. Enantiomeric discrimination of chiral amines with new fluorescent chemosensors. Chem Commun 1998:1747-1748.
16. Grady T, Harris SJ, Smyth MR, Diamond D. Determination of Enantiomeric Composition of chiral amines based on the quenching of the fluorescence of a chiral calixarene. Anal Chem 1996;68:3775-3782.
17. Lin J, Hu QS, Xu MH, Pu L. A practical enantioselective fluorescent sensor for mandelic acid. J Am Chem Soc 2002;124:2088-2089.
18. Pugh VJ, Hu QS, Pu L. The first dendrimer-based enantioselective fluorescent sensor for the recognition of chiral amino alcohols. Angew Chem Int Ed Engl 2000;39:3638-3641.
19. Vogtle F, Knops P. Dyes for visual distinction between enantiomers: crown ethers as optical sensors for chiral compounds. Angew Chem Int Ed Engl 1991;30:958-959.
20. Ueno A. Fluorescent sensors and color indicators for molecules. Adv Mater 1993;5:132-134.
21. Ikeda H, Nakamura M, Ise N, Oguma N, Nakamura A, Ikeda T, Toda F, Ueno A. Fluorescent cyclodextrins for molecule sensing: fluorescence properties, NMR characterization and inclusion phenomena of N-dansylleucine-modified cyclodextrins. J Am Chem Soc 1996;118: 10980-10988.
22. Wang J, Ueno A. Naphthol-modified beta-cyclodextrins as fluorescent sensors for detecting contaminants in drinking water. Macromol Rapid Commun 2000;21:887-890.
23. Ueno A, Ikeda A, Ikeda H, Ikeda T, Toda F. Fluorescent cyclodextrins responsive to molecules and metal ions. Fluorescence properties and inclusion phenomena of N-alpha-dansyl-L-lysine-beta-cyclodextrin and monensin-incorporated N-alpha-dansyl-L-lysine-beta-cyclodextrin. J Org Chem 1999;64:382-387.
24. Tanabe T, Touma K, Hamasaki K, Ueno A. Immobilized fluorescent cyclodextrin on a cellulose membrane as a chemosensor for molecule detection. Anal Chem 2001;73:3126-3130.
25. Liu Y, Han B-H, Sun S-X, Wada T, Inoue Y. Molecular recognition study on supramolecular systems. 20. Molecular recognition and enantioselectivity of aliphatic alcohols by L-tryptophan-modified β-cyclodextrin. J Org Chem 1999;64:1487-1493.
26. Impellizzeri G, Maccarrone G, Rizzarelli E, Vecchio G, Corradini R, Marchelli R. 6-Deoxy-6-N-histamino-β-cyclodextrin copper(II) complex, a new enantioselective receptor for aromatic amino acids. Angew Chem Int Ed Engl 1991;30:1348-1349.
27. Corradini R, Dossena A, Impellizzeri G, Maccarrone G, Marchelli R, Rizzarelli E, Sartor G, Vecchio G. Chiral recognition and separation of amino acids by means of a copper(II) complex of histamine monofunctionalized β-cyclodextrin. J Am Chem Soc 1994;116:10267-10274.
28. Bonomo RP, Cucinotta V, D'Alessandro F, Impellizzeri G, Maccarrone G, Rizzarelli E, Vecchio G, Carima L, Corradini R, Sartor G, Marchelli R. Chiral recognition by the copper(II) complex of 6-deoxy-6-N-(2-methylaminopyridine)-beta-cyclodextrin. Chirality 1997;9:341-349.
29. Corradini R, Dossena A, Marchelli R, Panagia A, Sartor G, Saviano M, Lombardi A, Pavone V. Amodified cyclodextrin with a fully encapsulated dansyl group: self-inclusion in the solid state and in solution. Chem Eur J 1996;2:373-381.
30. Corradini R, Dossena A, Galaverna G, Marchelli R, Panagia A, Sartor G. Fluorescent chemosensor for organic guests and copper(II) ion based on dansyldiethylenetriamine-modified beta-cyclodextrin. J Org Chem 1997;18:6283-6289.
31. Davankov VA. 30 years of chiral ligand exchange. Enantiomer 2000;5: 209-223.
32. Davankov VA, Navratil JD, Walton HF. Ligand exchange chromatography. Boca Raton, FL: CRC Press; 1988.
33. Galaverna G, Corradini R, Dallavalle F, Folesani G, Dossena A, Marchelli R. Chiral separation of amino acids by copper(II) complexes of tetradentate diaminodiamido-type ligands added to the eluent in reversed-phase high-performance liquid chromatography: a ligand exchange mechanism. J Chromatogr A 2001;922:151-163.
34. Galaverna G, Corradini R, Dossena A, Chiavaro E, Marchelli R, Dallavalle F, Folesani G. Chiral discrimination of Dns- and unmodified D,L-amino acids by copper(II) complexes of terdentate ligands in high-performance liquid chromatography. J Chromatogr A 1998;829:101-113.
35. Dallavalle F, Folesani G, Pelosi G, Ferrari MB, Galaverna G, Corradini R, Marchelli R. Copper(II) complexes with chiral diaminodiamido ligands: solution and structural studies. J Coord Chem 2000;51:135-151.
36. Pagliari S, Corradini R, Galaverna G, Sforza S, Dossena A, Marchelli R. Enantioselective sensing of amino acids by copper(II) complexes of phenylalanine-based fluorescent beta-cyclodextrins. Tetrahedron Lett 2000;41:3691-3695.
37. Prodi L, Montalti M, Zaccheroni N, Dallavalle F, Folesani G, Lanfranchi M, Corradini R, Pagliari S, Marchelli R. Dansylated polyamines as fluorescent sensors for metal ions: Photophysical properties and stability of copper(II) complexes in solution. Helvetica Chim Acta 2001; 84:690-706.
38. Pirkle W, Pochapsky TC. Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers. Chem Rev 1989;89:347-362.
39. Dallavalle F, Folesani G, Marchelli R, Galaverna G. Stereoselective formation of ternary copper(II) complexes of (S)-amino-acid amides and (R)-amino or (S)-amino acids in aqueous-solution. Helv Chim Acta 1994;77:1623-1630.
40. Hershenson FM. Synthesis of 4-keto-4,5,6,7-tetrahydroindoles via munchnone intermediates. J Org Chem 1975;40:1260-1264.
41. Sforza S, Corradini R, Ghirardi S, Dossena A, Marchelli R. DNA binding of a D-lysine-based chiral PNA: direction control and mismatch recognition. Eur J Org Chem 2000:2905-2913.
42. Hamasaki K, Ikeda H, Nakamura A, ueno A, Toda F, Suzuki I, Osa T. Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence. J Am Chem Soc 1993;115:5035-5040.