Chiral Differentiation of Some Cyclopentane and Cyclohexane β-Amino Acid Enantiomers Through Ion/Molecule Reactions

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 7, 2009, Pages 1235-1241

  Hyyryläinen, Anna R M ^a   Pakarinen, Jaana M H ^a   Forró, Eniko ^b   Fülöp, Ferenc ^b   Vainiotalo, Pirjo ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

18-CROWN-6; AMINO ACID ENANTIOMERS; CHIRAL CENTERS; CHIRAL HOST MOLECULES; ENANTIOMERIC PAIRS; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY; HOST GUEST COMPLEXES; ION/MOLECULE REACTIONS; TETRACARBOXYLIC ACID;

AMINATION; AMINO ACIDS; CROWN ETHERS; CYCLOHEXANE; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; ORGANIC ACIDS;

AMINES;

2 AMINOCYCLOPENTANECARBOXYLIC ACID; BETA AMINO ACID; BETA CYCLODEXTRIN; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE; CYCLOHEXYLAMINE DERIVATIVE; CYCLOPENTANE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOMER; INFRARED SPECTROSCOPY;

AMINO ACIDS; BETA-CYCLODEXTRINS; CROWN ETHERS; CYCLOHEXANES; CYCLOPENTANES; ETHYLAMINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 67649378628     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2009.02.018     Document Type: Article

References (43)

1. Steed J.W., and Atwood J.L. Supramolecular Chemistry (2000), Wiley, Chichester, England 88-92 321-334
2. Vögtle F. Supramolecular Chemistry (1991), Wiley, Chichester, England 27-32
3. Li S., and Purdy W.C. Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 92 (1992) 1457-1470
4. Connors K.A. The stability of cyclodextrin complexes in solution. Chem. Rev. 97 (1997) 1325-1357
5. Sallas F., and Darcy R. Amphiphilic cyclodextrins - Advances in synthesis and supramolecular chemistry. Eur. J. Org. Chem. (2008) 957-969
6. Ward T.J. Chiral separations. Anal. Chem. 74 (2002) 2863-2872
7. Hembury G.A., Borovkov V.V., and Inoue Y. Chirality-sensing supramolecular systems. Chem. Rev. 108 (2008) 1-73
8. Hoffmann C.V., Pell R., Lämmerhofer M., and Lindner W. Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC. Anal. Chem. 80 (2008) 8780-8789
9. Péter A., and Fülöp F. High-performance liquid chromatographic method for the separation of isomers of cis- and trans-2-amino-cyclopentane-1-carboxylic acid. J. Chromatogr. A 715 (1995) 219-226
10. Nishi H., Nakamura K., Nakai H., and Sato T. Separation of enantiomers and isomers of amino compounds by capillary electrophoresis and high-performance liquid chromatography utilizing crown ethers. J. Chromatogr. A 757 (1997) 225-235
11. Hyun M.H., Tan G., and Xue J.Y. Unusual resolution of N-(3,5-dinitrobenzoyl)-α-amino acids on a chiral stationary phase based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid. J. Chromatogr. A 1097 (2005) 188-191
12. Berkecz R., Ilisz I., Fülöp F., Pataj Z., Hyun M.H., and Péter A. High-performance chromatographic enantioseparation of β-3-homo-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based stationary phase. J. Chromatogr. A 1189 (2008) 285-291
13. Tanaka Y., Otsuka K., and Terabe S. Separation of enantiomers by capillary electrophoresis-mass spectrometry employing a partial filling technique with a chiral crown ether. J. Chromatogr. A 875 (2000) 323-330
14. Zhou L., Lin Z., Reamer R.A., Mao B., and Ge Z. Stereoisomeric separation of pharmaceutical compounds using CE with a chiral crown ether. Electrophoresis 28 (2007) 2658-2666
15. Bunke A., and Jira T. Use of cationic cyclodextrin for enantioseparation by capillary electrophoresis. J. Chromatogr. A 798 (1998) 275-280
16. Szejtli J., and Juvancz Z. The role of cyclodextrins in chiral selective chromatography. Trends Anal. Chem. 21 (2002) 379-388
17. Sicoli G., Jiang Z., Jicsinsky L., and Schurig V. Modified linear dextrins ("acyclodextrins") as new chiral selectors for the gas-chromatographic separation of enantiomers. Angew. Chem. Int. Ed. 44 (2005) 4092-4095
18. Patrick J.S., Kotiaho T., McLuckey S.A., and Cooks R.G. Thermochemical determinations by the kinetic method. Mass Spectrom. Rev. 13 (1994) 287-339
19. Tao W.A., Zhang D., Wang F., Thomas P.D., and Cooks R.G. Kinetic resolution of D,L-amino acids based on gas-phase dissociation of Copper(II) complexes. Anal. Chem. 71 (1999) 4427-4429
20. Speranza M. Enantioselectivity in gas-phase ion-molecule reactions. Int. J. Mass Spectrom. 232 (2004) 277-317
21. Vincenti M. Host-guest chemistry in the mass spectrometer. J. Mass Spectrom. 30 (1995) 925-939
22. Schalley C.A. Molecular recognition and supramolecular chemistry in the gas phase. Mass Spectrom. Rev. 20 (2001) 253-309
23. Brodbelt J.S. Analytical applications of ion-molecule reactions. Mass Spectrom. Rev. 16 (1997) 91-110
24. Schug K.A., and Lindner W. Chiral molecular recognition for the detection and analysis of enantiomers by mass spectrometric methods. J. Sep. Sci. 28 (2005) 1932-1955
25. Sawada M. Chiral recognition detected by fast atom bombardment mass spectrometry. Mass Spectrom. Rev. 16 (1997) 73-90
26. Takai Y., Yamada H., Nishida J., Kaneda T., Arakawa R., Okamoto M., Hirose K., Tanaka T., Naemura K., and Sawada M. Chiral amino acid recognition detected by electrospray ionization (ESI) and fast atom bombardment (FAB) mass spectrometry (MS) coupled with the enantiomer-labeled (EL) guest method. J. Chem. Soc. Perkin Trans 2 (1998) 701-710
27. Daniel J.M., Friess S.D., Rajagopalan S., Wendt S., and Zenobi R. Quantitative determination of noncovalent binding interactions using soft ionization mass spectrometry. Int. J. Mass Spectrom. 216 (2002) 1-27
28. Kellersberger K.A., Dejsupa C., Liang Y., Pope R.M., and Dearden D.V. Gas phase studies of ammonium-cyclodextrin compounds using Fourier transform ion cyclotron resonance. Int. J. Mass Spectrom. 193 (1999) 181-195
29. Chu I.H., Bradshaw J.S., Huszthy P., Izatt R.M., and Dearden D.V. Chiral host-guest recognition in an ion-molecule reaction. J. Am. Chem. Soc. 115 (1993) 4318-4320
30. Dejsupa C., Liang Y., Bradshaw J.S., Izatt R.M., and Dearden D.V. Intrinsic contributions to chiral recognition: discrimination between enantiomeric amines by dimethyldiketopyridino-18-crown-6 in the gas phase. J. Am. Chem. Soc. 119 (1997) 353-359
31. Liang Y., Bradshaw J.S., and Dearden D.V. The thermodynamic basis for enantiodiscrimination: Gas-phase measurement of the enthalpy and entropy of chiral amine recognition by dimethyldiketopyridino-18-crown-6. J. Phys. Chem. A 106 (2002) 9665-9671
32. Ramirez J., Ahn S., Grigorean G., and Lebrilla C.B. Evidence for the formation of gas-phase inclusion complexes with cyclodextrins and amino acids. J. Am. Chem. Soc. 122 (2000) 6884-6890
33. Ahn S., Ramirez J., Grigorean G., and Lebrilla C.B. Chiral recognition in gas-phase cyclodextrin: amino acid complexes-is the three point interaction still valid in the gas phase?. J. Am. Soc. Mass Spectrom. 12 (2001) 278-287
34. Grigorean G., and Lebrilla C.B. Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions. Anal. Chem. 73 (2001) 1684-1691
35. Grigorean G., Cong X., and Lebrilla C.B. Chiral analysis of peptides by ion/molecule reactions. Int. J. Mass Spectrom. 234 (2004) 71-77
36. Fülöp F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem. Rev. 101 (2001) 2181-2204
37. Fülöp F., Martinek T.A., and Tóth G.K. Application of alicyclic β-amino acids in peptide chemistry. Chem. Soc. Rev. 35 (2006) 323-334
38. Hyyryläinen A.R.M., Pakarinen J.M.H., Fülöp F., and Vainiotalo P. Differentiation of diastereomeric cyclic β-amino acids by varying the neutral reagent in ion/molecule reactions studied by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. Rapid Commun. Mass Spectrom. 22 (2008) 1-8
39. de Koning L.J., Nibbering N.M.M., van Orden S.L., and Laukien F.H. Mass selection of ions in a Fourier transform ion cyclotron resonance trap using correlated harmonic excitation fields (CHEF). Int. J. Mass Spectrom. 165/166 (1997) 209-219
40. Ahn S., Cong X., Gronert S., and Lebrilla C.B. Zwitterion formation in gas-phase cyclodextrin complexes. J. Am. Soc. Mass Spectrom. 16 (2005) 166-175
41. Cong X., Czerwieniec G., McJimpsey E., Ahn S., Troy F.A., and Lebrilla C.B. Structural relationships in small molecule interactions governing gas-phase enantioselectivity and zwitterionic formation. J. Am. Soc. Mass Spectrom. 17 (2006) 442-452
42. Botta B., Subissati D., Tafi A., Monache G.D., Filippi A., and Speranza M. Cavity effects on the enantioselectivity of chiral amino[4]resorcinarene stereoisomers. Angew. Chem. Int. Ed. 43 (2004) 4767-4770
43. Hyyryläinen A.R.M., Pakarinen J.M.H., Stájer G., Fülöp F., and Vainiotalo P. Diastereochemical differentiation of β-amino acids using host-guest complexes studied by Fourier transform ion cyclotron resonance mass spectrometry. J. Am. Soc. Mass Spectrom. 18 (2007) 1038-1045