Highly dynamic motion of crown ethers along oligolysine peptide chains

Nature Chemistry

Volumn 1, Issue 7, 2009, Pages 573-577

  Weimann, Dominik P ^a   Winkler, Henrik D F ^a   Falenski, Jessica A ^a   Koksch, Beate ^a   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER; DRUG DERIVATIVE; LYSINE; OLIGOPEPTIDE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; BINDING SITE; CHEMISTRY; DEUTERIUM HYDROGEN EXCHANGE; MOTION; SYNTHESIS;

BINDING SITES; CROWN ETHERS; DEUTERIUM EXCHANGE MEASUREMENT; LYSINE; MOTION; OLIGOPEPTIDES; QUATERNARY AMMONIUM COMPOUNDS;

EID: 70349556565     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.352     Document Type: Article

References (28)

1. Meot-Ner (Mautner), M. The ionic hydrogen bond. Chem. Rev. 105, 213-284 (2005).
2. Lifshitz, C. A review of gas-phase H/D exchange experiments: The protonated arginine dimer and bradykinin nonapeptide systems. Int. J. Mass Spectrom. 234, 63-70 (2004).
3. Kellersberger, K. A., Desjupa, C., Liang, Y. J., Pope, R. M. & Dearden, D. V. Gas phase studies of ammonium-cyclodextrin compounds using Fourier transform ion cyclotron resonance. Int. J. Mass Spectrom. 193, 181-195 (1999).
4. Ventola, E., Rissanen, K. & Vainiotalo, P. Mass spectrometric investigation of noncovalent complexation between a tetratosylated resorcarene and alkyl ammonium ions. Chem. Eur. J. 10, 6152-6162 (2004).
5. Ventola, E., Hyyrylaäinen, A. & Vainiotalo, P. Complex formation between a tetramesityl sulfonated resorcarene and alkylammonium ions: A mass spectrometric study of noncovalent interactions. Rapid Commun. Mass Spectrom. 20, 1218-1224 (2006).
6. Kalenius, E., Moiani, D., Dalcanale, E. & Vainiotalo, P. Measuring H-bonding supramolecular complexes by gas phase ion-molecule reactions. Chem. Commun. 3865-3867 (2007).
7. Wood, T. D. et al. Gas-phase folding and unfolding of cytochrome c cations. Prod. Natl Acad. Sci. USA 92, 2421-2454 (1995).
8. Wyttenbach, T. & Bowers, M. T. Gas phase conformations of biological molecules: The hydrogen/deuterium exchange mechanism. J. Am. Soc. Mass Spectrom. 10, 9-14 (1999).
9. Lee, S.-W., Lee, H.-N., Kim, H. S. & Beauchamp, J. L. 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. J. Am. Chem. Soc. 120, 5800-5805 (1998).
10. Lias, S. G. Thermoneutral isotope exchange-reactions in proton-bound complexes of water with organic-molecules - correlations with energetics of formation of the corresponding association ions. J. Phys. Chem. 88, 4401-4407 (1984).
11. Cram, D. J. & Cram, J. M. Design of complexes between synthetic hosts and organic guests. Acc. Chem. Res. 11, 8-14 (1978).
12. Ruädiger, V. et al. Crown ether-ammonium complexes: binding mechanisms and solvent effects. Eur. J. Org. Chem. 1847-1856 (1999).
13. Maleknia, S. & Brodbelt, J. Cavity-size-dependent dissociation of crown ether/ammonium ion complexes in the gas phase. J. Am. Chem. Soc. 115, 2837-2843 (1993).
14. Dearden, D. V., Liang, Y. J., Nicoll, J. B. & Kellersberger, K. A. Study of gas-phase molecular recognition using Fourier transform ion cyclotron resonance mass spectrometry (FTICR/MS). J. Mass Spectrom. 36, 989-997 (2001).
15. Dearden, D. V., Desjupa, C., Liang, Y. J., Bradshaw, J. S. & Izatt, R. M. Intrinsic contributions to chiral recognition: Discrimination between enantiomeric amines by dimethyldiketopyridino-18-crown-6 in the gas phase. J. Am. Chem. Soc. 119, 353-359 (1997).
16. Wu, H. F. & Brodbelt, J. S. Comparison of the orders of gas-phase basicities and ammonium ion affinities of polyethers by the kinetic method and ligandexchange technique. J. Am. Soc. Mass Spectrom. 4, 718-722 (1993).
17. Liou, C.-C. & Brodbelt, J. S. Comparison of gas-phase proton and ammonium ion affinities of crown ethers and related acyclic analogs. J. Am. Chem. Soc. 114, 6761-6764 (1992).
18. Dearden, D. V. & Chu, I.-H. Relative ammonium ion affinities of 18-crown-6 and the isomers of dicyclohexano-18-crown-6. J. Incl. Phenomena Mol. Recogn. 29, 269-282 (1997).
19. Julian, R. R. & Beauchamp, J. L. The unusually high proton affinity of aza-18- crown-6 ether: Implications for the molecular recognition of lysine in peptides by lariat crown ethers. J. Am. Soc. Mass. Spectrom. 13, 493-498 (2002).
20. 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).
21. Fenn, J. B., Mann, M., Meng, C. K., Wong, S. F. & Whitehouse, C. M. Electrospray ionization for mass spectrometry of large biomolecules. Science 246, 64-71 (1989).
22. Marshall, A. G., Hendrickson, C. S. & Jackson, G. S. Fourier transform ion cyclotron resonance mass spectrometry: A primer. Mass Spectrom. Rev. 17, 1-35 (1998).
23. Hofstadler, S. A., Sannes-Lowery, K. A. & Griffey, R. H. A gated-beam electrospray ionization source with an external ion reservoir. A new tool for the characterization of biomolecules using electrospray ionization mass spectrometry Rapid Commun. Mass. Spectrom. 13, 1971-1979 (1999).
24. Hofstadler, S. A., Sannes-Lowery, K. A. & Griffey, R. H. Enhanced gas-phase hydrogen-deuterium exchange of oligonucleotide and protein ions stored in an external multipole ion reservoir. J. Mass. Spectrom. 35, 62-70 (2000).
25. Campbell, S., Rodgers, M. T., Marzluff, E. M. & Beauchamp, J. L. Deuterium exchange reactions as a probe of biomolecule structure. Fundamental studies of gas phase H/D exchange reactions of protonated glycine oligomers with D2O, CD3OD, CD3CO2D, and ND3. J. Am. Chem. Soc. 117, 12840-12854 (1995).
26. Cox, H. A., Julian, R. R., Lee, S.W. & Beauchamp, J. L. Gas-Phase H/D exchange of sodiated glycine oligomers with ND3: Exchange kinetics do not reflect parent ion structures. J. Am. Chem. Soc. 126, 6485-6490 (2004).
27. Freitas, M. A. & Marshall, A. G. Rate and extent of gas-phase hydrogen/deuterium exchange of bradykinins: Evidence for peptide zwitterions in the gas phase. Int. J. Mass Spectrom. 182-183, 221-231 (1999).
28. 3OD: Solution-phase structures in the gas phase. J. Am. Soc. Mass Spectrom. 18, 512-516 (2007).