ESI-mass spectrometry analysis of unsubstituted and disubstituted β-cyclodextrins: Fragmentation mode and identification of the AB, AC, AD regioisomers

Journal of the American Society for Mass Spectrometry

Volumn 14, Issue 2, 2003, Pages 124-135

  Sforza, Stefano ^a   Galaverna, Gianni ^a   Corradini, Roberto ^a   Dossena, Arnaldo ^a   Marchelli, Rosangela ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRIC POTENTIAL; MASS SPECTROMETRY; SUBSTITUTION REACTIONS;

REGIOISOMERS;

ISOMERS;

BETA CYCLODEXTRIN; FUNCTIONAL GROUP; SODIUM CHLORIDE; BETA CYCLODEXTRIN DERIVATIVE; CYCLODEXTRIN; PEPTIDE FRAGMENT;

MASS SPECTROMETRY;

ANALYZER; ARTICLE; ELECTRIC POTENTIAL; FRAGMENTATION REACTION; IONIZATION; ISOMER; MASS SPECTROMETRY; STATISTICAL ANALYSIS; STATISTICAL MODEL; SUBSTITUTION REACTION; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ISOMERISM; METHODOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BETA-CYCLODEXTRINS; CYCLODEXTRINS; ISOMERISM; MOLECULAR STRUCTURE; PEPTIDE FRAGMENTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037805235     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1044-0305(02)00853-X     Document Type: Article

References (25)

1. Atwood J. L.; Davies J. E.; MacNicol D.; Vogtle F.; Lehn J. M. Comprehensive Supramolecular Chemistry; Elsevier Science Ltd.: Oxford, 1996, Vol. III.
2. Li S., Purdy W.C. Circular Dichroism, Ultraviolet, and Proton Nuclear Magnetic Resonance Spectroscopic Studies of the Chiral Recognition Mechanism of β-Cyclodextrin. Anal. Chem. 64:1992;1405-1412.
3. Szejtli J. Cyclodextrin Technology. 1988;Kluwer Academic, Dordrecht.
4. Lehn J.-M. Supramolecular Chemistry. 109:1995;44-45 VCH, Weinheim.
5. Szejtli J. Introduction and General Overview on Cyclodextrin Chemistry. Chem. Rev. 98:1998;1743-1753.
6. Wenz G. Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units. Angew. Chem. Int. Ed. Engl. 33:1994;803-822.
7. Khan A.R., Forgo P., Stine K.J.D.', Souza V.T. Methods for Selective Modifications of Cyclodextrins. Chem. Rev. 98:1998;1977-1996.
8. Fujita K., Matsunaga A., Imoto T. 6A6B, 6A6C, and 6A6D-ditosylates of β-Cyclodextrin. Tetrahedron Lett. 25:1984;5533-5536.
9. Fujita K., Yamamura H., Imoto T. Unsymmetrically Disubstituted β-Cyclodextrins. 6A,6X-Dideoxy-6A-azido-6X-[(mesitylsulfonyl)oxy] Derivatives. J. Org. Chem. 50:1985;4393-4395.
10. Tabushi I., Yamamura K., Nabeshima T. Characterization of Regiospecific A,C- and A,D-Disulfonate Capping of β-Cyclodextrin. Capping as an Efficient Production Technique. J. Am. Chem. Soc. 106:1984;5267-5270.
11. Tabushi I., Nabeshima T., Fujita K., Matsunaga A., Imoto T. Regiospecific A,B Capping onto β-Cyclodextrin. Characteristic Remote Substituent Effect on 13C NMR Chemical Shift and Specific Taka-Amylase Hydrolysis. J. Org. Chem. 50:1985;2638-2643.
12. Breslow R., Canary J.W., Varney M., Waddell S.T., Yang D. Artifical Transaminases Linking Pyridoxamine to Binding Cavities Controlling the Geometry . J. Am. Chem. Soc. 112:1990;5212-5219.
13. Galaverna G., Paganuzzi M.C., Corradini R., Dossena A., Marchelli R. Enantiomeric Separation of Hydroxy Acids and Carboxylic Acids by Diamino-β-Cyclodextrins (AB, AC, AD) in Capillary Electrophoresis. Electrophoresis. 22:2001;3171-3177.
14. Tabushi I., Nabeshima T., Yamamura K., Fujita K. 400 MHz Two-Dimensional NMR Studies of Cyclodextrin Derivatives for 1H and 13C Chemical Shift Determination. Bull. Chem. Soc. Japan. 60:1987;3705-3712.
15. Yamamura H., Nagaoka H., Saito K., Kawai M., Butsugan Y., Nakajima T., Fujita K. Determination of the Structure of Tris(6-O-mesitylenesulfonyl)-α-Cyclodextrin Regioiomers by 1H NMR Analyses of the Corresponding 3,6-Anhydrocyclodextrin Derivatives. J. Org. Chem. 58:1993;2936-2937.
16. Yuan D.Q., Koga K., Yamagushi M., Fujita K. Synthesis and Unique NMR Behavior of a Novel Capped α-Cyclodextrin. J. Chem. Soc. Chem. Commun. 16:1996;1943-1944.
17. Cucinotta V.D., Alessandro F., Impellizzeri G., Pappalardo G., Rizzarelli E., Vecchio G. Cyclopeptide Functionalized β-Cyclodextrin. A New Class of Potentially Enzyme Mimicking Compounds with Two Recognition Sites. J. Chem. Soc. Chem. Commun. 5:1991;293-294.
18. Bonomo P.R., Impellizzeri G., Pappalardo G., Rizzarelli E., Vecchio G. Cyclo-L-Histidyl-L-Histidyl Capped β-Cyclodextrin. A New Potentially Enzyme-Mimicking Compound or Artificial Receptor with Two Recognition Sites. Gaz. Chim. Ital. 123:1993;593-595.
19. Tabushi I., Nabeshima T. Regiospecific A,B Capping onto β-Cyclodextrin. Characteristic Remote Substituent Effect on 13C NMR Chemical Shift and Specific Taka-Amylase Hydrolysis. J. Org. Chem. 50:1985;2638-2643.
20. Tabushi I., Kuroda Y., Yokota K., Yuan L.C. Regiospecific A,C- and A,D-Disulfonate Capping of β-Cyclodextrin. J. Am. Chem. Soc. 103:1981;711-712.
21. Fujita K., Yamamura H., Matsunaga A., Imoto T., Mihashi K., Fujioka T. 6-Polysubstituted α-Cyclodextrins. Application of Koerner's Absolute Method of Isomer Determination. J. Am. Chem. Soc. 108:1986;4509-4513.
22. E-Tri(O-sulfonyl)-β- Cyclodextrins. Tetrahedron Lett. 41:2000;8117-8120.
23. Yamamura H., Iida D., Araki S., Kobayashi K., Katakai R., Kano K., Kawai M. Polysulfonylated Cyclodextrins. Part II. Preparation and Structural Validation of Three Isomeric Pentakis(6-O-mesitylsulfonyl)cyclomaltoheptaoses. J. Chem. Soc. Perkin Trans. 1. 21:1999;3111-3115.
24. Pearce A.J., Sinay P. Diisobutylaluminum-Promoted Regioselective De-O-benzylation of Perbenzylated Cyclodextrins A Powerful New Strategy for the Preparation of Selectively Modified Cyclodextrins . Angew. Chem. Int. Ed. Engl. 39:2000;3610-3612.
25. Hanessian S., Benalil A., Laferriere C. The Synthesis of Functionalized Cyclodextrins as Scaffolds and Templates for Molecular Diversity, Catalysis, and Inclusion Phenomena. J. Org. Chem. 60:1995;4786-4797.