Chiral discrimination on the host-guest complexation of resorc[4]arenes with quarternary amines

European Journal of Mass Spectrometry

Volumn 10, Issue 5, 2004, Pages 649-655

  Mehdizadeh, Ahmad ^a   Letzel, Matthias C ^a   Klaes, Michael ^a   Agena, Ceno ^a   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Calixarene; Chiral discrimination recognition; Electrospray mass spectrometry; Host guest chemistry; Resorc 4 arene

Indexed keywords

AMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; ENANTIOMER; ISOTOPE ANALYSIS; MASS; NUCLEAR MAGNETIC RESONANCE; OPTICAL ROTATION; REACTION ANALYSIS; SYNTHESIS;

AMINES; CALIXARENES; HYDROCARBONS; QUATERNARY AMMONIUM COMPOUNDS; RESORCINOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 10044252167     PISSN: 14690667     EISSN: None     Source Type: Journal    
DOI: 10.1255/ejms.675     Document Type: Article

References (33)

1. (a) C.A. Schalley, R.K. Castellano, M.S. Brody, D.M. Rudkevich, G. Siuzdak and J. Rebek, Jr, "Investigating Molecular Recognition by Mass Spectrometry: Characterization of Calixarene-Based Self-Assembling Capsule Hosts with Charged Guests", J. Am. Chem. Soc. 121, 4568 (1999);
2. (b) M. Makinen, P. Vainiotalo and K. Rissanen, "Alkali metal mediated resorcarene capsules: An ESI-FTICRMS study on gas-phase structure and cation binding of tetraethyl resorcarene and its per-methylated derivative", J. Am. Soc. Mass Spectrom. 13, 851 (2002);
3. (c) A. Shivanyuk, M. Saadioui, F. Broda, I. Thondorf, M.O. Vysotsky, K. Rissanen, E. Kolehmainen and V. Böhmer, "Sterically and Guest-Controlled Self-Assembly of Calix[4]arene Derivatives", Chem. Eur. J. 10, 2138 (2004);
4. (d) M. Lehn, "Supramolecular Chemistry - Scope and Perspectives Molecules, Supermolecules, and Molecular Devices", Angew. Chem. Int. Ed. 27, 89 (1988);
5. (e) B. Linton and A.D. Hamilton, "Formation of Artificial Receptors by Metal-Templated Self-Assembly", Chem. Rev. 97, 1669 (1997); S.J. Cantrill, D.A. Fulton, A.M. Heiss, A.R. Pease, J.F. Stoddart, A.J.P. White and D.J. Williams, "Molecular Meccano, Part 60: The Influence of Macrocyclic Polyether Constitution upon Ammonium Ion/Crown Ether Recognition Processes", Chem. Eur. J. 6, 2274 (2000);
6. (e) B. Linton and A.D. Hamilton, "Formation of Artificial Receptors by Metal-Templated Self-Assembly", Chem. Rev. 97, 1669 (1997); S.J. Cantrill, D.A. Fulton, A.M. Heiss, A.R. Pease, J.F. Stoddart, A.J.P. White and D.J. Williams, "Molecular Meccano, Part 60: The Influence of Macrocyclic Polyether Constitution upon Ammonium Ion/Crown Ether Recognition Processes", Chem. Eur. J. 6, 2274 (2000);
7. (f) A. Shivanyuk and J. Rebek, "Hydrogen-bonded capsules in polar, protic solvents", Chem. Commun. 2374 (2001);
8. (g) A.W. Coleman, A.N. Lazar and E. Da Silva, in Encyclopedia of Supramolecular Chemistry, Ed by J.L. Atwood and J.W. Steed. Marcel Dekker, New York, USA, pp. 137-144, (2004);
9. (h) I. Stibor and P. Lhoták, in Encyclopedia of Supramolecular Chemistry, Ed by J.L. Atwood and J.W. Steed. Marcel Dekker, New York, USA, pp. 145-152, (2004);
10. M.V. Rekharsky, H. Yamamura, M. Kawai and Y. Inoue, "Critical Difference in Chiral Recognition of N-Cbz-D/L-aspartic and -glutamic Acids by Mono- and Bis(Trimethylammonio)-β-cyclodextrins", J. Am. Chem. Soc. 123, 5360 (2001).
11. (a) J.L. Beck, M.L. Colgrave, S.F. Ralph and M.M. Sheil, "Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals, and proteins", Mass Spectrom. Rev. 20, 61 (2001);
12. (b) M.L. Colgrave, C.J. Bramwell and C.S. Creaser, "Nanoelectrospray ion mobility spectrometry and ion trap mass spectrometry studies of the non-covalent complexes of amino acids and peptides with polyethers", Int. J. Mass Spectrom. 229, 209 (2003).
13. M. Sawada, "Chiral Recognition detected by Fast Atom Bombardment Mass Spectrometry", Mass Spectrom. Rev. 16, 73 (1997).
14. M. Sawada, Y. Takai, H. Yamada, M. Yoshikawa, R. Arakawa, H. Tabuchi, M. Takada, J. Tanaka, M. Shizuma, H. Yamaoka, K. Hirose, K. Fukuda and Y. Tobe, "Depression of the apparent chiral recognition ability obtained in the host-guest complexation systems by electrospray and nano-electrospray ionization mass spectrometry", Eur. J. Mass Spectrom. 10, 27 (2004).
15. (a) S. Ahn, J. Ramirez, G. Grigorean and C.B. Lebrilla, "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, 278 (2001);
16. (b) C.B. Lebrilla, "The gas-phase chemistry of cyclodextrin inclusion complexes", Acc. Chem. Res. 34, 653 (2001);
17. (c) Y. Liang, J.S. Bradshaw and D.V. Dearden, "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, 9665 (2002);
18. (d) D. Scuderi, A. Paladini, M. Satta, D. Catone, A. Filippi, S. Piccirillo, A. Lagana, M. Speranza and A. Giardini Guidoni, "Gas-phase complexes: noncovalent interactions and stereospecificity", Int. J. Mass Spectrom. 223/224, 159 (2003).
19. (a) C. Garcia, J. Guyot, G. Jeminet, E. Leize-Wagner, H. Nierengarten and A. Van Dorsselaer, "Chiral Recognition Properties of Spiroacetal Polyethers Using Electrospray Ionization Mass Spectrometry", Tetrahedron Lett. 40, 4997 (1999);
20. (b) H. Nierengarten, E. Leize, C. Garcia, G. Jeminet and A. Van Dorsselaer, "Electrospray Ionization Mass Spectrometry (ESI-MS): a powerful tool for the evaluation of chiral recognition in host-guest complexation", Analusis 28, 259 (2000).
21. M. Klaes, C. Agena, M. Köhler, M. Inoue, T. Wada, Y. Inoue and J. Mattay, "First Synthesis, Isolation and Characterization of Enantiomerically Pure and Inherently Chiral Resorc[4]arenes by Lewis Acid Cyclization of a Resorcinol Monoalkyl Ether", Eur. J. Org. Chem. 8, 1404 (2003).
22. M. Klaes, B. Neumann, H.-G. Stammler and J. Mattay, "Determination of the absolute configuration of inherently chiral resorcarenes", Eur. J. Org. Chem. submitted (2004).
23. F. Inokuchi, Y. Shiomi, H. Kawabata, T. Sakaki and S. Shinkai, "Alkali-metal selectivity of calix[n]aryl acetates as estimated by mass-spectrometry on the relative stability of the 2/1 metal calix[n]arene complex", Chem. Lett. 9, 1595 (1993).
24. F. Inokuchi, Y. Miyahara, T. Inazu and S. Shinkai, "Cation-PI interactions detected by mass-spectrometry-selective recognition of Alkali-metal cations by a PI-basic molecular cavity", Angew. Chem. Int. Ed. Engl. 34, 1364 (1995).
25. P.S.H. Wong, X.J. Yu and D.V. Dearden, "Complexes of p-tert-butylcalix[4]arene with mono- and dipositive cations in the gas phase", Inorg. Chem. Acta 246, 259 (1996).
26. M.C. Letzel, C. Agena and J. Mattay, "Investigation of homo- and heterodimer alkali metal cation complexes of resorc[4]arenes by electrospray ionization mass spectrometry", J. Mass Spectrom. 37, 63 (2002).
27. (a) The deuteration approach was invented by M. Sawada, Y. Takai, H. Yamada, S. Hirayama, T. Kaneda, T. Tankaka, K. Kamada, T. Mizooku, S. Takeuchi, K. Ueno, K. Hirose, Y. Tobe and K. Naemura, "Chiral recognition in host-guest complexation determined by the enantiomer-labeled guest method using Fast-Atom-Bombardment Mass-Spectrometry", J. Am. Chem. Soc. 117, 7726 (1995);
28. (b) M. Sawada, Y. Takai, T. Kaneda, R. Arakawa, M. Okamoto, H. Doe, T. Matsuo, K. Naemura, K. Hirose and Y. Tobe, "Chiral molecular recognition in electrospray ionization mass spectrometry", Chem. Commun. 1735 (1996).
29. Y.J. Liang, J.S. Bradshaw, R.M. Izatt, R.M. Pope and D.V. Dearden, "Analysis of enantiomeric excess using mass spectrometry: fast atom bombardment and electrospray ionization/Fourier transform mass spectrometric approaches", Int. J. Mass Spectrom. 187, 977 (1999).
30. J. Lacour, L. Vial and C. Herse, "Efficient NMR enantio- differentiation of chiral quats with BINPHAT anion", Org. Lett. 4, 1351 (2002).
31. The "◇"-sign indicates that the guest is labeled by deuterium, i.e. the methyl groups at the nitrogen are perdeuterated.
32. W. Schrader, A. Eipper, D.J. Pugh and M.T. Reetz, "Second-generation MS-based high-throughput screening system for enantioselective catalysts and biocatalysts", Can. J. Chem. 80, 626 (2002).
33. The ISIR value is defined in analogy to the IRIS value in References 3 and 4. In contrast to M. Sawada, our ISIR value just reflects the measured signal ratios and the chiral as well as the isotope effect.