Mass spectrometric study of oligourea macrocycles and their anion binding behavior

Journal of Mass Spectrometry

Volumn 44, Issue 9, 2009, Pages 1338-1347

  Becherer, Tobias ^a   Meshcheryakov, Denys ^b   Springer, Andreas ^a   Böhmer, Volker ^b   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Anion recognition; Gas phase chemistry; H D exchange; Hydrogen bonding; Macrocycles; Supramolecular chemistry; Urea compounds

Indexed keywords

ANION RECOGNITION; GAS-PHASE CHEMISTRY; H/D EXCHANGE; HYDROGEN BONDING; MACROCYCLES;

BINDING ENERGY; CHLORINE COMPOUNDS; ETHERS; HYDROGEN; MACROMOLECULES; MASS SPECTROMETERS; MASS SPECTROMETRY; METABOLISM; NEGATIVE IONS; SUPRAMOLECULAR CHEMISTRY; UREA;

HYDROGEN BONDS;

ANION; DIPHENYL ETHER; MACROCYCLIC COMPOUND; OLIGONUCLEOTIDE; UREA; XANTHENE;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON TRANSPORT; RECEPTOR BINDING; SYNTHESIS;

EID: 70349266036     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1616     Document Type: Article

References (26)

1. P. D. Beer, P. A. Gale. Anion recognition and sensing: the state of the art and future perspectives. Angewandte Chemie International Edition 2001, 40, 486. DOI: 10.1002/1521-3773(20010202)40:3〈486::AID-ANIE486〉3.0.CO;2-P.
2. P. A. Gale, P. Anzenbacher Jr, J. L. Sessler. Calixpyrroles II. Coordination Chemistry Reviews 2001, 222, 57. DOI: 10.1016/S0010- 8545(01)00346-350
3. J. L. Sessler, J. M. Davis. Sapphyrins: versatile anion binding agents. Accounts of Chemical Research 2001, 34, 989. DOI 10.1021/ar980117g.
4. F. P. Schmidtchen, M. Belger. Artificial organic host molecules for anions. Chemical Reviews 1997, 97, 1609. DOI: 10.1021/cr9603845.
5. V. Amendola, L. Fabrizzi, C. Mangano, P. Pallavicini, A. Poggi, A. Taglietti. Anion recognition by dimetallic cryptates. Coordination Chemistry Reviews 2001, 219-221, 821. DOI: 10.1016/S0010-8545(01)00368-X.
6. S. J. Brooks, S. E. García-Garrido, M. E. Light, P. A. Cole, P. A. Gale. Conformational control of selectivity and stability in hybrid Amide/Urea macrocycles. Chemistry-A European Journal 2007, 13, 3320. DOI: 10.1002/chem.200601647.
7. B. H. M. Snellink-Ruël, M. M. G. Antonisse, J. F. J. Engbersen, P. Timmermann, D. N. Reinhoudt. Neutral anion receptors with multiple urea- binding sites. European Journal of Organic Chemistry 2000, 1, 165. DOI: 10.1002/(SICI)1099-0690(200001)2000:1〈165::AIDEJOC165〉 3.0.CO;2-#.
8. R. Herges, A. Dikmans, U. Jana, F. Köhler, P. G. Jones, I. Dix, T. Fricke, B. König. Design of a neutral macrocyclic ionophore: synthesis and binding properties for nitrate and bromide anions. European Journal of Organic Chemistry 2002, 17, 3004. DOI: 10.1002/1099- 0690(200209)2002:17〈3004::AID- EJOC3004〉3.0.CO;2-O.
9. D. Ranganathan, C. Lakshmi. Cystine-based cyclic oligoureas: a new class of hydrogen-bonding electroneutral anion receptors. Chemical Communications 2001, 1250. DOI: 10.1039/b102720b.
10. C. R. Bondy, P. A. Gale, S. J. Loeb. Metal-organic anion receptors: arranging urea hydrogen-bond donors to encapsulate sulfate ions. Journal of the American Chemical Society 2004, 126, 5030. DOI: 10.1021/ja039712q S0002-7863(03)09712-9719
11. P. A. Gale. Amide- and urea-based anion receptors. Encyclopedia of Supramolecular Chemistry 2004, 31. DOI: 10.1081/E-ESMC 120012830.
12. D. Meshcheryakov, F. Arnaud-Neu, V. Böhmer, M. Bolte, V. Hubscher-Bruder, E. Jobin, I. Thondorf, S. Werner. Cyclic triureas-synthesis, crystal structures and properties. Organic and Biomolecular Chemistry 2008, 6, 1004. DOI: 10.1039/b718114k.
13. D. Meshcheryakov, V. Böhmer, M. Bolte, V. Hubscher-Bruder, F. Arnaud-Neu. Macrocyclic hexaureas: synthesis, conformation and anion binding. Chemistry-A European Journal 2009, 15, 4811. DOI: 10.1002./chem. 200802573.
14. D. Meshcheryakov, V. Böhmer, M. Bolte, V. Hubscher-Bruder, F. Arnaud-Neu, H. Herschbach, A. Van Dorsselaer, I. Thondorf, W. Mögelin. Two chloride ions as a template in the formation of a cyclic hexaurea. Angewandte Chemie International Edition 2006, 45, 1648. DOI: 10.1002/anie.200503766.
15. B. Baytekin, H. T. Baytekin, C. A. Schalley. Mass spectrometric studies of non-covalent compounds: why supramolecular chemistry in the gas phase? Organic and Biomolecular Chemistry 2006, 4, 2825. DOI: 10.1039/b604265a.
16. M. Kogej, C. A. Schalley. Mass spectrometry and gas phase chemistry of supramolecules. Analytical Methods in Supramolecular Chemistry. Wiley-VCH: Weinheim, 2006, 104.
17. M. Meot-Ner (Mautner). The ionic hydrogen bond. Chemical Reviews 2005, 105, 213. DOI: 10.1021/cr941178.
18. S. A. Hofstadler, K. A. Sannes-Lowery, R. H. Griffey. Journal of Mass Spectrometry 2000, 35, 62. DOI: 10.1002/(SICI)1096- 9888(200001)35:1〈62:: AID-JMS913〉3.0.CO;2-9.
19. S.-W. Lee, H.-N. Lee, H. S. Kim, J. L. Beauchamp. Selective binding of crown ethers to protonated peptides can be used to probe mechanisms of H/D exchange and collision-induced dissociation reactions in the gas phase. Journal of the American Chemical Society 1998, 120, 5800. DOI: 10.1021/ja980056h.
20. E. Ventola, K. Rissanen, P. Vainiotalo. Mass spectrometric investigation of noncovalent complexation between a tetratosylated resorcarene and alkyl ammonium ions. Chemistry-A European Journal 2004, 10, 6152. DOI: 10.1002/chem.200400431.
21. E. Ventola, A. Hyyrylainen, P. Vainiotalo. Complex formation betweenatetramesityl sulfonated resorcareneandalkylammonium ions: a mass spectrometric study of noncovalent interactions. Rapid Communications in Mass Spectrometry 2006, 20, 1218. DOI: 10.1002/rcm.2440.
22. E. Kalenius, D. Moiani, E. Dalcanale, P. Vainiotalo. Measuring H-bonding supramolecular complexes by gas phase ion-molecule reactions. Chemical Communications 2007, 3865. DOI: 10.1039/b707842k.
23. T. Wyttenbach, M. T. Bowers. Gas phase conformations of biological molecules: the hydrogen/deuterium exchangemechanism. Journal of the American Society for Mass Spectrometry 1999, 10, 9. DOI: 10.1016/S1044-0305(98)00121-4.
24. 3- anions do not exist. Journal of Physical Chemistry 1994, 98, 2298. DOI: 10.1021/j100060a015.
25. 2-, and some related species. Journal of the American Chemical Society 1994, 116, 10761. DOI: 10.1021/ja00102a046.
26. 2- and its solvation stabilization. Journal of Chemical Physics 2000, 113, 10837. DOI: 10.1063/1.1333703.