View PDF Version
 
DOI: 10.1039/A705567F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1709-1714

EPR investigation on radical trap reactions of 2-methyl-2-nitrosopropane encapsulated by cyclodextrins with external organic radicals produced by photolysis of coenzyme B12 and its analogues

(Note: The full text of this document is currently only available in the PDF Version )

Lai Bin Luo, De Yan Han, Yue Wu, Xin Yi Song and Hui Lan Chen

Abstract

1H NMR studies reveal that 2-methyl-2-nitrosopropane (MNP) in the dimeric state can decompose into monomer effectively in the presence of cyclodextrins (Cds) in aqueous solution. The inclusion complexes formed are more soluble than MNP itself and stable to light. MNP–Cds are used as radical traps in the photolysis of coenzyme B12 and alkylcobalamins in the present study. The N and H hyperfine splitting parameters of the spin adducts are obtained by the EPR technique. Models for the interaction between Cds and aminoxyls are proposed, which mimic coenzyme B12–enzyme interactions to a certain extent.

References

  1. M. L. Bender and M. Komiyama, Cyclodextrin Chemistry, Springer, Berlin, 1978 Search PubMed.
  2. J. Szejtli, Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest, 1982 Search PubMed.
  3. G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803 CrossRef.
  4. R. Breslow, Acc. Chem. Res., 1995, 28, 146 CrossRef CAS.
  5. (a) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1995, 71 RSC; (b) S. R. McAlpine and A. Garcia-Garibay, J. Am. Chem. Soc., 1996, 118, 2750 CrossRef CAS; (c) U. H. Brinker, R. Buchkremer, M. Kolodziejczyk, R. Kupfer, M. Rosenberg, M. D. Poliks, M. Orlando and M. L. Gross, Angew. Chem., Int. Ed. Engl., 1993, 32, 1344 CrossRef; (d) E. Monflier, E. Blouet, Y. Barbaux and A. Mortreux, Angew. Chem., Int. Ed. Engl., 1994, 33, 2100 CrossRef.
  6. M. Lucarini and B. P. Roberts, Chem. Commun., 1996, 1557 RSC.
  7. M. Okazaki and K. Kuwata, J. Phys. Chem., 1984, 88, 3163 CrossRef CAS; ibid., 1984, 88, 4181 Search PubMed.
  8. Y. Kotake and E. G. Janzen, J. Am. Chem. Soc., 1989, 111, 2066 CrossRef CAS; ibid., 1989, 111, 5138 Search PubMed; ibid., 1989, 111, 7319 Search PubMed; ibid., 1992, 114, 2872 Search PubMed; M. Luarini and B. P. Roberts, Chem. Commun., 1996, 1577 Search PubMed.
  9. S. Kazma, S. Ihara, I. Morito, H. Yoshioka, M. Kamiya and Y. Akahori, Chem. Pharm. Bull., 1993, 41, 2022.
  10. Y. Motozato, T. Nishihara, C. Hirayama and Y. Furuya, Can. J. Chem., 1982, 60, 1959.
  11. K. Flohr, R. M. Paton and E. T. Kaiser, J. Am. Chem. Soc., 1975, 97, 1209 CrossRef CAS.
  12. J. Martinie, J. Michon and A. Rassat, J. Am. Chem. Soc., 1975, 97, 1818 CrossRef CAS.
  13. K. Kano, K. Mori, B. Uno, M. Goto and T. Kubota, J. Am. Chem. Soc., 1990, 112, 8645 CrossRef CAS.
  14. P. Boulas, W. Kutner, M. T. Jones and K. M. Kadish, J. Phys. Chem., 1994, 98, 1282 CrossRef CAS.
  15. C. Lagercrantz, J. Phys. Chem., 1971, 75, 3466 CrossRef CAS.
  16. (a) H. Yan, H. L. Chen, Y. Qian and W.-X. Tang, J. Inorg. Biochem., 1994, 56, 265 CrossRef CAS; (b) H. L. Chen, Y. Qian, G. J. Chen and W. X. Tang, Chin. Sci. Bull., 1991, 36, 42 Search PubMed; (c) H. Yan, Ph.D. Thesis, Nanjing University, 1993.
  17. (a) B12, ed. D. Dolphin, Wiley, New York, 1982 Search PubMed; (b) J. M. Pratt, Inorganic Chemistry of Vitamin B12, Academic Press, New York, 1972 Search PubMed.
  18. J. Halpern, Science, 1985, 227, 869 CAS.
  19. (a) R. G. Finke, in Molecular Mechanisms in Biorganic Processes, ed. C. Bleasdale and B. T. Golding, Royal Society of Chemistry, Cambridge, 1990, p. 224 Search PubMed; (b) R. G. Finke, D. A. Schiraldi and B. J. Mayer, Coord. Chem. Rev., 1984, 54, 1 CrossRef CAS.
  20. L. G. Marzilli, in Bioinorganic Catalysis, ed. J. Reedijk, Marcel Dekker, New York, 1993 Search PubMed.
  21. (a) C. D. Garr and R. G. Finke, J. Am. Chem. Soc., 1992, 114, 10 440 CrossRef CAS; (b) C. D. Garr and R. G. Finke, Inorg. Chem., 1993, 32, 4414 CrossRef.
  22. (a) H. L. Chen, H. Yan, H. Z. Sun and W. X. Tang, Synth. React. Inorg. Met.-Org. Chem., 1993, 23, 347 CrossRef CAS; (b) B. H. Zhu, Z. H. Liu, H. Yan, J. Liu and H. L. Chen, J. Inorg. Biochem., 1997, 65, 45 CrossRef CAS; (c) D. Dolphin, Inorg. Synth., 1982, 20, 152.
  23. J. C. Stowell, J. Org. Chem., 1971, 36, 3055 CrossRef CAS.
  24. N. M. Atherton and S. J. Strach, J. Chem. Soc., Faraday Trans. 1, 1975, 71, 357 RSC.
  25. C. Heller and H. M. McConnell, J. Chem. Phys., 1960, 32, 1535 CrossRef CAS.
  26. A. M. Calafat, S. Taoka, J. M. Puckett, C. Semerad, H. Yan, L. B. Luo, H. L. Chen, R. Banerjee and L. G. Marzilli, Biochemistry, 1995, 34, 14 125 CrossRef CAS.
  27. (a) P. G. Lenhert and D. C. Hodgkin, Nature (London), 1961, 192, 937 CAS; (b) P. G. Lenhert, Proc. R. Soc. London A, 1968, 303, 45 CAS; (c) H. F. J. Savage, P. F. Lindley, J. L. Finney and P. A. Timmins, Acta Crystallogr., Sect. B, 1987, 43, 296 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.