Alkali Metal-Cationized Serine Clusters Studied by Sonic Spray Ionization Tandem Mass Spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 18, Issue 5, 2007, Pages 856-868

  Nanita, Sergio C ^a   Sokol, Ewa ^a   Cooks, R Graham ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; IONIZATION; MASS SPECTROMETRY; POSITIVE IONS;

HOMOCHIRALITY; OCTAMERS; TETRAMERS;

ALKALI METALS;

ALKALI METAL; CESIUM; LITHIUM; METAL ION; POTASSIUM; RUBIDIUM; SERINE; SODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; FRAGMENTATION REACTION; IONIZATION; TANDEM MASS SPECTROMETRY;

CATIONS; METALS, ALKALI; NEBULIZERS AND VAPORIZERS; SERINE; SONICATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 34247280627     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2007.01.003     Document Type: Article

References (65)

1. Hofstadler S.A., and Griffey R.H. Analysis of Noncovalent Complexes of DNA and RNA by Mass Spectrometry. Chem. Rev 101 (2001) 377-390
2. Borman S. Quadruplex Proposals. Chem. Eng. News 80 (2002) 36-37
3. Borman S. Quadruplex Seen in Human Cells. Chem. Eng. News 80 (2002) 9
4. Fukushima K., and Iwahashi H. 1:1 Complex of Guanine Quartet with Alkali Metal Cations Detected by Electrospray Ionization Mass Spectrometry. Chem. Commun (2000) 895-896
5. Freisinger E., Schimanski A., and Lippert B. Thymine-Metal Ion Interactions: Relevance for Thymine Quartet Structures. J. Biol. Inorg. Chem 6 (2001) 378-389
6. Koch K.J., Aggerholm T., Nanita S.C., and Cooks R.G. Clustering of Nucleobases with Alkali Metals Studied by Electrospray Ionization Mass Spectrometry: Implications for Mechanisms of Multistrand DNA Stabilization. J. Mass Spectrom 37 (2002) 676-686
7. Tirumala S., and Davis J.T. Self-Assembled Ionophores. An Isoguanosine-K+ Octamer. J. Am. Chem. Soc 119 (1997) 2769-2776
8. Mezzina E., Mariani P., Itri R., Masiero S., Pieraccini S., Spada G.P., Spinozzi F., Davis J.T., and Gottarelli G. The Self-Assembly of a Lipophilic Guanosine Nucleoside into Polymeric Columnar Aggregates: The Nucleoside Structure Contains Sufficient Information to Drive the Process Towards a Strikingly Regular Polymer. Chem. Eur. J 7 (2001) 388-395
9. Aggerholm T., Nanita S.C., Koch K., and Cooks R.G. Clustering of Nucleosides in the Presence of Alkali Metals. Biologically Relevant Quartets of Guanosine, Deoxyguanosine, and Uridine Observed by Electrospray Ionization Tandem Mass Spectrometry. J. Mass Spectrom 38 (2003) 87-97
10. Canty A.J., Colton R., D'Agostino A., and Traeger J.C. Positive and Negative Ion Electrospray Mass Spectrometric Studies of Some Amino Acids and Glutathione, and Their Interactions with Alkali Metal Ions and Methylmercury. II. Inorg. Chim. Acta 223 (1994) 103-107
11. Julian R.R., Hodyss R., and Beauchamp J.L. Salt Bridge Stabilization of Charged Zwitterionic Arginine Aggregates in the Gas Phase. J. Am. Chem. Soc 123 (2001) 3577-3583
12. Mark T.D. Mass Spectrometry of Clusters. Adv. Mass Spectrom 13 (1995) 71-94
13. Zhou S.L., and Hamburger M. Formation of Sodium Cluster Ions in Electrospray Mass Spectrometry. Rapid Commun. Mass Spectrom 10 (1996) 797-800
14. Zhang D., Wu L., Koch K.J., and Cooks R.G. Arginine Clusters Generated by Electrospray Ionization and Identified by Tandem Mass Spectrometry. Eur. Mass Spectrom 5 (1999) 353-361
15. 2+: Magic Numbers, Dissociation, and Structure. Int. J. Mass Spectrom 195/196 (2000) 667-684
16. Justes D.R., Mitric R., Moore N.A., Bonacic-Koutecky V., and Castleman A.W. Theoretical and Experimental Consideration of the Reactions between VxOy+ and Ethylene. J. Am. Chem. Soc 125 (2003) 6289-6299
17. Justes D.R., Moore N.A., and Castleman A.W. Reactions of Vanadium and Niobium Oxides with Methanol. J. Phys. Chem. B 108 (2004) 3855-3862
18. Dermota T.E., Zhong Q., and Castleman A.W. Ultrafast Dynamics in Cluster Systems. Chem. Rev 104 (2004) 1861-1886
19. Nemes P., Schlosser G., and Vékey K. Amino Acid Cluster Formation Studied by Electrospray Ionization Mass Spectrometry. J. Mass Spectrom 40 (2005) 43-49
20. Fenn J.B., Mann M., Meng C.K., Wong S.F., and Whitehouse C.M. Electrospray Ionization for Mass-Spectrometry of Large Biomolecules. Science 246 (1989) 64-71
21. Fenn J.B., Mann M., Meng C.K., Wong S.F., and Whitehouse C.M. Electrospray Ionization-Principles and Practice. Mass Spectrom. Rev 9 (1990) 37-70
22. Ramsey R.S., Van Berkel G.J., McLuckey S.A., and Glish G.L. Determination of Pyrimidine Cyclobutane Dimers by Electrospray Ionization/Ion Trap Mass Spectrometry. Biol. Mass Spectrom 21 (1992) 347-352
23. Little D.P., Chorush R.A., Speir J.P., Senko M.W., Kelleher N.L., and McLafferty F.W. Rapid Sequencing of Oligonucleotides by High-Resolution Mass Spectrometry. J. Am. Chem. Soc 116 (1994) 4893-4897
24. Przybylski M., and Glocker M.O. Electrospray Mass Spectrometry of Biomacromolecular Complexes with Noncovalent Interactions-New Analytical Perspectives for Supramolecular Chemistry and Molecular Recognition Processes. Angew. Chem. Int. Ed 35 (1996) 806-826
25. Loo J.A. Studying Noncovalent Protein Complexes by Electrospray Ionization Mass Spectrometry. Mass Spectrom. Rev 16 (1997) 1-23
26. Loo J.A. Electrospray Ionization Mass Spectrometry: A Technology for Studying Noncovalent Macromolecular Complexes. Int. J. Mass Spectrom 200 (2000) 175-186
27. Shelimov K.B., and Jarrold M.F. "Denaturation" and Refolding of Cytochrome c in Vacuo. J. Am. Chem. Soc 118 (1996) 10313-10314
28. Valentine S.J., Anderson J.G., Ellington A.D., and Clemmer D.E. Disulfide-Intact and -Reduced Lysozyme in the Gas Phase: Conformations and Pathways of Folding and Unfolding. J. Phys. Chem. B 101 (1997) 3891-3900
29. Hirabayashi A., Sakairi M., and Koizumi H. Sonic Spray Ionization Method for Atmospheric Pressure Ionization Mass Spectrometry. Anal. Chem 66 (1994) 4557-4559
30. Hirabayashi A., Sakairi M., and Koizumi H. Sonic Spray Mass Spectrometry. Anal. Chem 67 (1995) 2878-2882
31. Shiea J., Wang W.-S., Wang C.-H., Chen P.-S., and Chou C.-H. Analysis of a Reactive Dimethylenedihydrothiophene in Methylene Chloride by Low-Temperature Atmospheric Pressure Ionization Mass Spectrometry. Anal. Chem 68 (1996) 1062-1066
32. Yamaguchi K. Cold-Spray Ionization Mass Spectrometry: Principle and Applications. J. Mass Spectrom 38 (2003) 473-490
33. Takats Z., Wiseman J.M., Gologan B., and Cooks R.G. Electrosonic Spray Ionization. A Gentle Technique for Generating Folded Proteins and Protein Complexes in the Gas Phase and for Studying Ion-Molecule Reactions at Atmospheric Pressure. Anal. Chem 76 (2004) 4050-4058
34. Wiseman J.M., Takáts Z., Gologan B., Davisson V.J., and Cooks R.G. Direct Characterization of Enzyme-Substrate Complexes by Using Electrosonic Spray Ionization Mass Spectrometry. Angew. Chem. Int. Ed 44 (2005) 913-916
35. Takats Z., Nanita S.C., Cooks R.G., Schlosser G., and Vekey K. Amino Acid Clusters Formed by Sonic Spray Ionization. Anal. Chem 75 (2003) 1514-1523
36. Myung S., Julian R.R., Nanita S.C., Cooks R.G., and Clemmer D.E. Formation of Nanometer-Scale Serine Clusters by Sonic Spray. J. Phys. Chem. B 108 (2004) 6105-6111
37. Zhang, D.; Koch, K. J.; Tao, W. A.; Cooks, R. G. Proceedings of the 48th ASMS Conference on Mass Spectrometry and Allied Topics; Long Beach, CA, June 2000.
38. Cooks R.G., Zhang D., Koch K.J., Gozzo F.C., and Eberlin M.N. Chiroselective Self-Directed Octamerization of Serine: Implications for Homochirogenesis. Anal. Chem 73 (2001) 3646-3655
39. Hodyss R., Julian R.R., and Beauchamp J.L. Spontaneous Chiral Separation in Noncovalent Molecular Clusters. Chirality 13 (2001) 703-706
40. Counterman A.E., and Clemmer D.E. Magic Number Clusters of Serine in the Gas Phase. J. Phys. Chem. B 105 (2001) 8092-8096
41. Julian R.R., Hodyss R., Kinnear B., Jarrold M., and Beauchamp J.L. Nanocrystalline Aggregation of Serine Detected by Electrospray Ionization Mass Spectrometry: Origin of the Stable Homochiral Gas Phase Serine Octamer. J. Phys. Chem. B 106 (2002) 1219-1228
42. + Studied by Infrared Photodissociation Spectroscopy. Angew. Chem. Int. Ed 45 (2006) 4130-4134
43. Koch K.J., Gozzo F.C., Zhang D., Eberlin M.N., and Cooks R.G. Serine octamer metaclusters: Formation, Structure Elucidation, and Implications for Homochiral Polymerization. Chem. Commun (2001) 1854-1855
44. Koch K.J., Gozzo F.C., Nanita S.C., Takats Z., Eberlin M.N., and Cooks R.G. Chiral Transmission between Amino Acids: Chirally-Selective Amino Acid Substitution in the Serine Octamer as a Possible Step in Homochirogenesis. Angew. Chem. Int. Ed 41 (2002) 1721-1724
45. Schalley C.A., and Weis P. Unusually Stable Magic Number Clusters of Serine with a Surprising Preference for Homochirality. Int. J. Mass Spectrom 221 (2002) 9-19
46. Takats Z., Nanita S.C., and Cooks R.G. Serine Octamer Reactions: Indicators of Prebiotic Relevance. Angew. Chem. Int. Ed 42 (2003) 3521-3523
47. Takats Z., Nanita S.C., Schlosser G., Vekey K., and Cooks R.G. Atmospheric Pressure Gas-Phase H/D Exchange of Serine Octamers. Anal. Chem 75 (2003) 6147-6154
48. Ustyuzhanin P., Ustyuzhanin J., and Lifshitz C. An Electrospray Ionization-Flow Tube Study of H/D Eexchange in Protonated Serine. Int. J. Mass Spectrom 223-224 (2003) 491-498
49. Geller O., and Lifshitz C. An Electrospray Ionization-Flow Tube Study of H/D Exchange in the Protonated Serine Dimer and Protonated Serine Dipeptide. Int. J. Mass Spectrom 227 (2003) 77-85
50. Julian, R. R.; Myung, S.; Clemmer, D. E. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
51. Julian R.R., Myung S., and Clemmer D.E. Spontaneous Anti-Resolution in Heterochiral Clusters of Serine. J. Am. Chem. Soc 126 (2004) 4110-4111
52. Takats Z., and Cooks R.G. Thermal Formation of Serine Octamer Ions. Chem. Commun (2004) 444-445
53. Nanita, S. C.; Takats, Z.; Cooks, R. G. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
54. Nanita S.C., Takats Z., Myung S., Clemmer D.E., and Cooks R.G. Chiral Enrichment of Serine Via Formation, Dissociation, and Soft-Landing of Octameric Cluster Ions. J. Am. Soc. Mass Spectrom 15 (2004) 1360-1365
55. Hwang, H. Y.; Lin, C.; Oh, H.; Breuker, K.; Carpenter, B. K.; McLafferty, F. W. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
56. Hvelplund, P.; Rangama, J.; Liu, B.; Nielsen, A. B.; Nielsen, S. B.; Tomita, S. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
57. O'Hair, R. A. J.; Gronert, S.; Fagin, A. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
58. Mazurek, U.; Reuben, B. G.; McFarland, M. A.; Marshall, A. G.; Lifshitz, C. Proceedings of the 52nd ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 2004.
59. Gronert S., O'Hair R.A.J., and Fagin A.E. Ion/Molecule Reactions of the Protonated Serine Octamer. Chem. Commun (2004) 1944-1945
60. Mazurek U., McFarland M.A., Marshall A.G., and Lifshitz C. Isolation of Isomers Based on Hydrogen/Deuterium Exchange in the Gas Phase. Eur. J. Mass Spectrom 10 (2004) 755-758
61. Mazurek U., Geller O., Lifshitz C., McFarland M.A., Marshall A.G., and Reuben B.G. Protonated Serine Octamer Cluster: Structure Elucidation by Gas-Phase H/D Exchange Reactions. J. Phys. Chem. A 109 (2005) 2107-2112
62. Nanita S.C., and Cooks R.G. Negatively-Charged Halide Adducts of Homochiral Serine Octamers. J. Phys. Chem. B 109 (2005) 4748-4753
63. Nanita S.C., and Cooks R.G. Serine Octamers: Cluster Formation, Reactions, and Implications for Biomolecule Homochirality. Angew. Chem. Int. Ed 45 (2006) 554-569
64. Wong S.S., and Röllgen F.W. The Effect of a Glycerol Matrix on the Cluster Ion Formation from Salts in Secondary Ion Mass Spectrometry. Int. J. Mass Spectrom. Ion Processes 70 (1986) 135-144
65. Myung S., Fioroni M., Julian R.R., Koeniger S.L., Baik M.-H., and Clemmer D.E. Chirally Directed Formation of Nanometer-Scale Proline Clusters. J. Am. Chem. Soc 128 (2006) 10833-10839