Abstract
The use of electrospray ionization mass spectrometry (ESI/MS) for the detection of neutral organic molecules becomes possible by their derivation with specific ESI/MS tagging reagents that have either proton or metal ion binding sites. We used the neutral crown ether group in several reagents to attach a metal binding site to substrate molecules. Application of this method to steroids, amino acids, vitamin D, fatty acids, and fullerenes is described. Besides characterization, tagged molecules can be used for studying organic reactions by ESI/MS. This work demonstrates that ESI/MS provides a unique window on fullerene solution chemistry. ESI/MS is not only an excellent tool for the analysis of biopolymers but is also useful for studying the organic chemistry of small neutral molecules.
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Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Science 1989, 246, 64; (b) Fenn, J, B.; Mann, M.; Meng, C K.; Wong, S. F.; Whitehouse, C. M. Mass Spectrom. Rev. 1990, 9, 37; (c) Smith, R. D.; Loo, J. A.; Edmonds, C. G.; Barinage, C. J.; Udseth, H. R. Anal Chem. 1990, 62, 882; (d) Beavis, R. C.; Chait, B. T. Proc. Natl Acad. Sci. USA 1990, 87, 6873; (e) McEwen, C. N.; Larsen, B. S. J. Am, Soc. Mass Speclrom. 1991, 2, 205; (f) Dass, C; Kusmierz, J. J.; Desiderio, D. M.; Jaruis, S. A.; Green, B. N. J. Am. Soc. Mass Spectrom. 1991, 2, 149; (g) Guevremont, R.; Siu, K. W. M,; Le Blanc, J. C. Y.; Berman, S. S. J. Am. Soc. Mass Spectrom. 1992, 3, 216; (h) Chait, B. T.; Kent, S. B. H. Science, 1992, 257, 1885; (i) Loo, J. A.; Loo, R. R. O.; Light, K. J.; Edmonds, C. G.; Smith, R. D. Anal Chem. 1992, 64, 81.
Beckner, C.; Caprioli, R. Biomed. Environ. Mass Spectrom, 1984, 11, 60; (b) Caprioli, R. Anal. Chem. 1983, 55, 2387; (c) Johnstone, R. A. W.; Rose, M. E. J. Chem. Soc, Chem. Commun. 1983, 1268; (d) Ikarashi, Y.; Maruyama, Y. J. Chromatogr. 1991, 587, 306; (e) Newton, R. P.; Walton, T. J.; Brenton, A. G.; Kingston, E. E.; Harris, F, M. Rapid Commun. Mass Spectrom. 1989, 3(6), 178–182; (f) Brown, S. M.; Busch, K. L. Anal. Chim. Acta 1989, 218, 231; (g) Lustig, D, A.; Lubman, D. M. Rev. Sci. Instrum. 1991 62(4), 957–962; (h) Hahn, J. H.; Zenobi, R,; Zare, R. N. J. Am. Chem. Soc. 1987, 109, 2842; (i) Teesch, L. M.; Adams, J. Org. Mass Spectrom. 1992, 27, 931; (j) Brown, S. M.; Busch, K. L. Anal. Chim. Acta 1989, 218, 231; (k) DiDonato, G. C.; Busch, K. L. Biomed. Environ. Mass Spectrom. 1985, 12, 364; (I) Cuarini, A.; Guglielmetti, G,; Andriollo, Nunzio; Vmcenti, M. Anal Chem. 1992, 64, 204.
Cheng, Z. L.; Siu, K. W. M.; Guevremont, R.; Berman, S. S. J. Am. Soc. Mass Spectrom. 1992, 3, 281.
4. (a) Wilson, S. R.; Wu, Y. J. Org, Chem. 1992, 57, 6941; (b) Wilson, S. R.; Perez, J.; Wu, Y. Nat. Prod. Lett. 1992, 2, 103; (c) Wilson, S. R.; Wu, Y. Proceedings of the 40th ASMS Conference on Mass Spectrometry and Allied Topics; Washington, DC, 1992; p 594; (d) Wilson, S. R.; Tushinsky, M. L.; Wu, Y. Proceedings of the 40th ASMS Conference on Mass Spectrometry and Allied Topics; Washington, DC, 1992; p 1641; (e) Wilson, S. R.; Wu, Y. Organometallics, 1993, 12, 1478; (f) Perez, J. Ph.D. thesis, New York University, 1992; (g) Wilson, S. R.; Perez, J.; Pasternak, A. J. Am. Chem. Soc., 1993, 115, 1994; (h) Wilson, S. R.; Wu, Y., J. Chem. Soc. Chem. Commun., in press; (i) Wilson, S. R.; Wu, Y., J. Am. Chem. Soc., in press.
Van Berkel, G. J.; McLuckey, S. A.; Glish, G. L. Anal. Chem. 1992, 64, 1586.
Allen, M. H.; Vestal, M. L. J. Am. Soc. Mass Spectrom. 1992, 3, 18.
Wilson, S. R.; Tulchinski, M.; Wu, Y. Bioorg. Med. Chem. Lett., in press.
Aebersold, R.; Bures, E. J.; Namchuk, M.; Goghari, M. H.; Shushan, B.; Covey, T. C. Protein Sci. 1992, 1, 494.
Dole, M.; Mach, L. L.; Hines, R. L.; Mobley, R. C.; Ferguson, L. P.; Alice, M. B. J. Chem. Phys. 1968, 49, 2240; (b) Mach, L. L.; Kralik, P.; Rheude, A.; Dole, M. J. Chem. Phys. 1970, 52, 4977.
Katta, V.; Chowdhury, S. K.; Chait, B. T., J. Am. Chem. Soc. 1990, 112, 5348.
Simmons, M. G.; Wilson, L. J. J. Chem. Soc, Chem. Commun. 1978, 634.
Hutchens, T. W.; Allen, M. H. Rapid Commun. Mass Spectrom. 1992, 6, 469.
Lam, Z.; Reinhold, B. B.; Reinhold, V. N. Proceedings of the 39th ASMS Conference on Mass Spectrometry and Allied Topics; Nashville, TN, May 19-24, 1991; p 282.
Wilson, S. R.; Lu, Q.; Tulchinski, M.; Wu, Y. J. Chem. Soc. Chem. Commun., in press.
Wilson, S. R.; Tulchinski, M., unpublished results.
Koshland, D. Science 1991, 254, 1705.
Braun, T. Angew. Chem. Int. Ed. Engl 1992, 31, 588; (b) Wudl, F.; Hirsch, A.; Khemani, K. C; Suzuki, T.; Allemand, P.-M.; Koch, A.; Eckert, H.; Srdanov, G.; Webb, H. M. In Fullerenes; ACS Symposium Series; American Chemical Society: Washington, DC, 1992; (c) Hirsch, A.; Khemani, K. C.; Suzuki, T.; Allermand, P.-M.; Kolch, A.; Srdanov, G.; Wudl, F. In Large Carbon Clusters; ACS Symposium Series; American Chemical Society: Washington, DC, 1991; (d) Howard, J. B.; McKinon, J. T.; Makarovsky, Y.; Lafleur, A. L.; Johnson, E. Nature 1991, 352, 139–141; (e) Coustel, N.; Bernier, P.; Aznar, R.; Zahad, A.; Lamber, L.-M.; Lyard, P. J. Chem., Soc, Chem. Commun, 1992, 1402; (f) Scrievens, W. A.; Bedworth, P. V.; Tour, J. M.; J. Am. Chem. Soc. 1992, 114, 7917; (g) Khemani, K. C; Prato, M.; Wudl, F. J. Org. Chem. 1992, 57, 3254; (h) Schwarz, H. Angew. Chem. Int Ed. Engl. 1992, 31, 293; (i) Wudl, F. Acc. Chem. Res. 1992, 25, 157; (j) Hoke, S. H., II; Molstad, J.; Dilettato, D.; Jay, M. J.; Carlson, D.; Kahr, B.; Cooks, K. G. J. Org. Chem. 1992, 57, 5069.
McElvany, S. W.; Ross, M. M. J. Am. Soc. Mass. Spectrom. 1992, 3, 268.
Wilson, S. R.; Tulchmski, M, submitted.
Olah, G. A.; Bucsi, J.; Lambert, C.; Aniszfeld, R.; Truverdi, N. J.; Sensharman, D. K.; Prakash, G. K. S. J. Am. Chem. Soc. 1991, 112, 9385.
Cahill, P. A.; Henderson, C. C. MRS Meeting Abstracts, Boston, MA, Dec. 1992.
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Wilson, S.R., Wu, Y. Applications of electrospray ionization mass spectrometry to neutral organic molecules including fullerenes. J Am Soc Mass Spectrom 4, 596–603 (1993). https://doi.org/10.1016/1044-0305(93)85021-O
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DOI: https://doi.org/10.1016/1044-0305(93)85021-O