Chemistry inside molecular containers in the gas phase

Nature Chemistry

Volumn 5, Issue 5, 2013, Pages 376-382

  Lee, Tung Chun ^a   Kalenius, Elina ^b   Lazar, Alexandra I ^c   Assaf, Khaleel I ^c   Kuhnert, Nikolai ^c   Grün, Christian H ^d   Jänis, Janne ^e   Scherman, Oren A ^a   Nau, Werner M ^c  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^c JACOBS UNIVERSITY BREMEN   (Germany)

^d UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

^e UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84876863991     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1618     Document Type: Article

References (50)

1. Cram, D. J. Molecular container compounds. Nature 356, 29-36 (1992
2. Mal, P., Breiner, B., Rissanen, K. & Nitschke, J. R. White phosphorus is air-stable within a self-assembled tetrahedral capsule. Science 324, 1697-1699 (2009
3. Gibb, C. L. D., Sundaresan, A. K., Ramamurthy, V. & Gibb, B. C. Templation of the excited-state chemistry of alpha-(n-alkyl) dibenzyl ketones: How guest packing within a nanoscale supramolecular capsule influences photochemistry. J. Am. Chem. Soc. 130, 4069-4080 (2008
4. Kang, J. & Rebek, J. Jr Acceleration of a Diels-Alder reaction by a self-assembled molecular capsule. Nature 385, 50-52 (1997
5. Yoshizawa, M., Tamura, M. & Fujita, M. Diels-Alder in aqueous molecular hosts: Unusual regioselectivity and efficient catalysis. Science 312, 251-254 (2006
6. Schmidtchen, F. P. Macrotricyclic quaternary ammonium salts: Enzymeanalogous activity. Angew. Chem. Int. Ed. Engl. 20, 466-468 (1981
7. Hooley, R. J., Biros, S. M. & Rebek, J. Jr A deep, water-soluble cavitand acts as a phase-transfer catalyst for hydrophobic species. Angew. Chem. Int. Ed. 45, 3517-3519 (2006
8. Pluth, M. D., Bergman, R. G. & Raymond, K. N. Acid catalysis in basic solution: A supramolecular host promotes orthoformate hydrolysis. Science 316, 85-88 (2007
9. Koblenz, T. S., Wassenaar, J. & Reek, J. N. H. Reactivity within a confined self-assembled nanospace. Chem. Soc. Rev. 37, 247-262 (2008
10. Dong, Z. Y., Luo, Q. & Liu, J. Q. Artificial enzymes based on supramolecular scaffolds. Chem. Soc. Rev. 41, 7890-7908 (2012
11. Schalley, C. A. Molecular recognition and supramolecular chemistry in the gas phase. Mass Spectrom. Rev. 20, 253-309 (2001
12. Jiang, W. & Schalley, C. A. Tandem mass spectrometry for the analysis of self-sorted pseudorotaxanes: The effects of Coulomb interactions. J. Mass Spectrom. 45, 788-798 (2010
13. Pluth, M. D. & Raymond, K. N. Reversible guest exchange mechanisms in supramolecular host-guest assemblies. Chem. Soc. Rev. 36, 161-171 (2007
14. Nuwaysir, L. M., Castoro, J. A., Yang, C. L. C. & Wilkins, C. L. Gas-phase host guest chemistry of carcerands and hemicarcerands. J. Am. Chem. Soc. 114, 5748-5751 (1992
15. van Wageningen, A. M. A. et al. Calix[4]arene-based (hemi)carcerands and carceplexes: Synthesis, functionalization, and molecular modeling study. Chem. Eur. J. 3, 639-654 (1997
16. Schalley, C. A. et al. Structural examination of supramolecular architectures by electrospray ionization mass spectrometry. Eur. J. Org. Chem. 1325-1331 (1999
17. Schalley, C. A., Verhaelen, C., Klärner, F-G., Hahn, U. & Vögtle, F. Gas-phase host-guest chemistry of dendritic viologens and molecular tweezers: A remarkably strong effect on dication stability. Angew. Chem. Int. Ed. 44, 477-480 (2005
18. Kalenius, E., Moiani, D., Dalcanale, E. & Vainiotalo, P. Measuring H-bonding supramolecular complexes by gas phase ion-molecule reactions. Chem. Commun. 3865-3867 (2007
19. Kalenius, E., Koivukorpi, J., Kolehmainen, E. & Vainiotalo, P. Noncovalent saccharide recognition by means of a tetrakis(bile acid)-porphyrin conjugate: Selectivity, cooperation, and stability. Eur. J. Org. Chem. 1052-1058 (2010
20. Zhang, H. Z., Paulsen, E. S., Walker, K. A., Krakowiak, K. E. & Dearden, D. V. Cucurbit[6]uril pseudorotaxanes: Distinctive gas-phase dissociation and reactivity. J. Am. Chem. Soc. 125, 9284-9285 (2003
21. Dearden, D. V. et al. One ring to bind them all: Shape-selective complexation of phenylenediamine isomers with cucurbit[6]uril in the gas phase. J. Phys. Chem. A 113, 989-997 (2009
22. Zhang, H., Grabenauer, M., Bowers, M. T. & Dearden, D. V. Supramolecular modification of ion chemistry: Modulation of peptide charge state and dissociation behavior through complexation with cucurbit[n]uril (n= 5, 6) or a-cyclodextrin. J. Phys. Chem. A 113, 1508-1517 (2009
23. Julian, R. R., May, J. A., Stoltz, B. M. & Beauchamp, J. L. Biomimetic approaches to gas phase peptide chemistry: Combining selective binding motifs with reactive carbene precursors to form molecular mousetraps. Int. J. Mass Spectrom. 228, 851-864 (2003
24. Julian, R. R., May, J. A., Stoltz, B. M. & Beauchamp, J. L. Molecular mousetraps: Gas-phase studies of the covalent coupling of noncovalent complexes initiated by reactive carbenes formed by controlled activation of diazo precursors. Angew. Chem. Int. Ed. 42, 1012-1015 (2003
25. Schalley, C. A. & Springer, A. Mass Spectrometry and Gas-Phase Chemistry of Non-Covalent Complexes. Supramolecular Chemistry in the Gas Phase (Wiley, 2009
26. Vrkic, A. K., O'Hair, R. A. J. & Lebrilla, C. B. Unusual covalent bond-breaking reactions of beta-cyclodextrin inclusion complexes of nucleobases/nucleosides and related guest molecules. Eur. J. Mass Spectrom. 9, 563-577 (2003
27. Heo, S. W. et al. Host-guest chemistry in the gas phase: Selected fragmentations of CB[6]-peptide complexes at lysine residues and its utility to probe the structures of small proteins. Anal. Chem. 83, 7916-7923 (2011
28. Brinker, U. H. & Miesset, J-L. Molecular Encapsulation: Organic Reactions in Constrained Systems (John Wiley & Sons, 2010
29. Carrera, S. S., Kerdelhué, J-L., Langenwalter, K. J., Brown, N. & Warmuth, R. Inner-phase reaction dynamics: The influence of hemicarcerand polarizability and shape on the potential energy surface of an inner-phase reaction. Eur. J. Org. Chem. 2239-2249 (2005
30. Warmuth, R., Kerdelhué, J-L., Carrera, S. S., Langenwalter, K. J. & Brown, N. Rate acceleration through dispersion interactions: Effect of a hemicarcerand on the transition state of inner phase decompositions of diazirines. Angew. Chem. Int. Ed. 41, 96-99 (2002
31. Nau, W. M., Florea, M. & Assaf, K. I. Deep inside cucurbiturils: Physical properties and volumes of their inner cavity determine the hydrophobic driving force for host-guest complexation. Isr. J. Chem. 51, 559-577 (2011
32. Florea, M. & Nau,W. M. Strong binding of hydrocarbons to cucurbituril probed by fluorescent dye displacement: A supramolecular gas-sensing ensemble. Angew. Chem. Int. Ed. 50, 9338-9342 (2011
33. Lagona, J., Mukhopadhyay, P., Chakrabarti, S. & Isaacs, L. The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844-4870 (2005
34. Mock, W. L. & Shih, N. Y. Host-guest binding capacity of cucurbituril. J. Org. Chem. 48, 3618-3619 (1983
35. Wang, R., Yuan, L. & Macartney, D. H. Cucurbit[7]uril mediates the stereoselective [4+4] photodimerization of 2-aminopyridine hydrochloride in aqueous solution. J. Org. Chem. 71, 1237-1239 (2006
36. Klöck, C., Dsouza, R. N. & Nau, W. M. Cucurbituril-mediated supramolecular acid catalysis. Org. Lett. 11, 2595-2598 (2009
37. Koner, A. L., Ma'rquez, C., Dickman, M. H. & Nau, W. M. Transition-metalpromoted chemoselective photoreactions at the cucurbituril rim. Angew. Chem. Int. Ed. 50, 545-548 (2011
38. Lee, J. W., Samal, S., Selvapalam, N., Kim, H. J. & Kim, K. Cucurbituril homologues and derivatives: New opportunities in supramolecular chemistry. Acc. Chem. Res. 36, 621-630 (2003
39. Ma'rquez, C., Hudgins, R. R. & Nau, W. M. Mechanism of host-guest complexation by cucurbituril. J. Am. Chem. Soc. 126, 5806-5816 (2004
40. Biedermann, F., Uzunova, V. D., Scherman, O. A., Nau, W. M., De Simone, A. Release of high-energy water as an essential driving force for the high-affinity binding of cucurbit[n]urils. J. Am. Chem. Soc. 134, 15318-15323 (2012
41. Bakirci, H., Koner, A. L., Dickman, M. H., Kortz, U. & Nau,W. M. Dynamically self-assembling metalloenzyme models based on calixarenes. Angew. Chem. Int. Ed. 45, 7400-7404 (2006
42. Adam, W. & Miranda, M. A. Thermal and photochemical reactions of bicyclic azoalkanes in concentrated sulfuric acid. J. Org. Chem. 52, 5498-5500 (1987
43. Adam, W., Harrer, H. M., Nau, W. M. & Peters, K. Electronic substituent effects on the acid-catalyzed [4+2] cycloaddition of isopyrazoles with cyclopentadiene and the photochemical and thermal denitrogenation of the resulting 1,4-diaryl- 7,7-dimethyl-2,3-diazabicyclo[2.2.1]hept-2-ene azoalkanes to bicyclo[2.1.0]pentanes. J. Org. Chem. 59, 3786-3797 (1994
44. Turecěk, F. & Hanuš, V. Retro-Diels-Alder reaction in mass spectrometry. Mass Spectrom. Rev. 3, 85-152 (1984
45. Ma'rquez, C. & Nau, W. M. Two mechanisms of slow host-guest complexation between cucurbit[6]uril and cyclohexylmethylamine: PH-responsive supramolecular kinetics. Angew. Chem. Int. Ed. 40, 3155-3160 (2001
46. Griffin, L. L. & Mcadoo, D. J. The effect of ion size on rate of dissociation - RRKM calculations on model large polypeptide ions. J. Am. Soc. Mass Spectrom. 4, 11-15 (1993
47. Vekey, K. Internal energy effects in mass spectrometry. J. Mass Spectrom. 31, 445-463 (1996
48. Lifshitz, C. Tropylium ion formation from toluene - solution of an old problem in organic mass spectrometry. Acc. Chem. Res. 27, 138-144 (1994
49. Mecozzi, S. & Rebek, J. Jr The 55% solution: A formula for molecular recognition in the liquid state. Chem. Eur. J. 4, 1016-1022 (1998
50. Ajami, D. et al. Encapsulated carboxylic acid dimers with compressed hydrogen bonds. Angew. Chem. Int. Ed. 50, 528-531 (2011