Synthesis of isomeric analogues of coenzyme pyrroloquinoline quinone (PQQ)

Synthesis

Volumn , Issue 3, 1996, Pages 377-382

  Zhang, Zhoupeng ^b   Tillekeratne, L M V ^a,b   Hudson, Richard A ^b  

^a UNIVERSITY OF TOLEDO   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLOQUINOLINEQUINONE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0029877996     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4226     Document Type: Article

References (44)

1. Salisbury, S. A.; Forrest, H. S.; Cruse, W. B. T.; Kennard, O. Nature (London). 1979, 280, 843. Duine, J. A.; Frank, J. Jr.; Van Zeeland, J. K. FEBS Lett. 1979, 108, 443.
2. Salisbury, S. A.; Forrest, H. S.; Cruse, W. B. T.; Kennard, O. Nature (London). 1979, 280, 843. Duine, J. A.; Frank, J. Jr.; Van Zeeland, J. K. FEBS Lett. 1979, 108, 443.
3. Klinman, J. P.; Mu, D. Ann. Rev. Biochem. 1994, 63, 299. Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993. Pierpoint, W. S. Trends Biochem. Sci. 1990, 15, 299.
4. Klinman, J. P.; Mu, D. Ann. Rev. Biochem. 1994, 63, 299. Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993. Pierpoint, W. S. Trends Biochem. Sci. 1990, 15, 299.
5. Klinman, J. P.; Mu, D. Ann. Rev. Biochem. 1994, 63, 299. Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993. Pierpoint, W. S. Trends Biochem. Sci. 1990, 15, 299.
6. McIntire, W. S. Essays Biochem. 1992, 27, 119. Duine, J. A. Eur. J. Biochem. 1991, 200, 271.
7. McIntire, W. S. Essays Biochem. 1992, 27, 119. Duine, J. A. Eur. J. Biochem. 1991, 200, 271.
8. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
9. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
10. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
11. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
12. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
13. Steinberg, F. M.; Gershwin, M. E.; Rucker, R. B. J. Nutri. 1994, 124, 744. Steinberg, F. M.; Rucker, R. B. In Modern Nutrition in Health and Disease; Shils, M. E.; Olson, J. A.; Shike, M., Eds.; Lea & Febiger: Pennsylvania, 1994; Vol 1, p 473. Steinberg, F. M.; Amidt, C.; Kilgore, J.; Romero-Chapman, N.; Tran, D.; Bui, D.; Rucker, R. B. In Principles of Applications of Quinoproteins; Davidson, V. L., Ed.; Marcel Dekker: New York, 1993; p 367. Smidt, C. R.; Steinberg, F. M.; Rucker, R. B. Proc. Soc. Expl. Biol. Med. 1991, 197, 19. Gibbons, W. Science News 1991, 139, 332. Killgore, J.; Smidt, C.; Duich, L.; Romero-Chapman, N.; Tinker, D.; Reiser, K.; Melko, M.; Hyde, D.; Rucker, R. B. Science 1989, 245, 850.
14. Quandt, K. S.; Hultquist, D. E. Proc. Natl. Acad. Sci. USA 1994, 91, 9322. Christensen, H. N. Nutri. Rev. 1994, 52, 24. Xu, F.; Mack, C. P.; Quandt, K. S.; Shlafer, M.; Massey, V.; Hultquist, D. E. Biochem. Biophys. Res. Commun. 1993, 193, 434. Hultquist, D. E.; Xu, F.; Quandt, K.S.; Shlafer, M.; Mack, C. P.; Till, G. O.; Seekamp, A.; Betz, A. L.; Ennis, S. R. Am. J. Hematol. 1993, 42, 13.
15. Quandt, K. S.; Hultquist, D. E. Proc. Natl. Acad. Sci. USA 1994, 91, 9322. Christensen, H. N. Nutri. Rev. 1994, 52, 24. Xu, F.; Mack, C. P.; Quandt, K. S.; Shlafer, M.; Massey, V.; Hultquist, D. E. Biochem. Biophys. Res. Commun. 1993, 193, 434. Hultquist, D. E.; Xu, F.; Quandt, K.S.; Shlafer, M.; Mack, C. P.; Till, G. O.; Seekamp, A.; Betz, A. L.; Ennis, S. R. Am. J. Hematol. 1993, 42, 13.
16. Quandt, K. S.; Hultquist, D. E. Proc. Natl. Acad. Sci. USA 1994, 91, 9322. Christensen, H. N. Nutri. Rev. 1994, 52, 24. Xu, F.; Mack, C. P.; Quandt, K. S.; Shlafer, M.; Massey, V.; Hultquist, D. E. Biochem. Biophys. Res. Commun. 1993, 193, 434. Hultquist, D. E.; Xu, F.; Quandt, K.S.; Shlafer, M.; Mack, C. P.; Till, G. O.; Seekamp, A.; Betz, A. L.; Ennis, S. R. Am. J. Hematol. 1993, 42, 13.
17. Quandt, K. S.; Hultquist, D. E. Proc. Natl. Acad. Sci. USA 1994, 91, 9322. Christensen, H. N. Nutri. Rev. 1994, 52, 24. Xu, F.; Mack, C. P.; Quandt, K. S.; Shlafer, M.; Massey, V.; Hultquist, D. E. Biochem. Biophys. Res. Commun. 1993, 193, 434. Hultquist, D. E.; Xu, F.; Quandt, K.S.; Shlafer, M.; Mack, C. P.; Till, G. O.; Seekamp, A.; Betz, A. L.; Ennis, S. R. Am. J. Hematol. 1993, 42, 13.
18. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
19. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
20. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
21. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
22. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
23. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
24. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
25. Narutomi, Y.; Katsumata, M.; Osawa, Y. and Uchikuga, S. European Patent Appl. EP 262345 (1988); Chem. Abstr. 1988, 109, 222458. Narutomi, Y.; Katsumata, M.; Osawa, Y.; Uchikuga, S. US Patent 4895870 (1990); Chem. Abstr. 1990, 113, 65272. Nakamura, A.; Inoue, Y.; Uragam, S. Japanese Patent 01 283221 (1989); Chem. Abstr. 1990, 113, 52500. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 63156724 (1988); Chem. Abstr. 1988, 109, 176333.
26. Hobara, N.; Watanabe, A.; Kobayashi, M.; Tsuji, T.; Gomita, Y.; Araki, Y. Pharmacology 1988, 37, 264. Watanabe, M.; Yoshihara, N.; Iwayama, A. Japanese Pat. 63192717 (1988); Chem. Abstr. 1989, 110, 69400.
27. Hobara, N.; Watanabe, A.; Kobayashi, M.; Tsuji, T.; Gomita, Y.; Araki, Y. Pharmacology 1988, 37, 264. Watanabe, M.; Yoshihara, N.; Iwayama, A. Japanese Pat. 63192717 (1988); Chem. Abstr. 1989, 110, 69400.
28. Hobara, N.; Watanabe, A.; Kobayashi, M.; Tsuji, T.; Gomita, Y.; Araki, Y. Pharmacology 1988, 37, 264. Watanabe, M.; Yoshihara, N.; Iwayama, A. Japanese Pat. 63192717 (1988); Chem. Abstr. 1989, 110, 69400.
29. Matsutani, Y.; Sugawara, T.; Kurobe, H.; Takahashi, J.; Moriguchi, Y.; Endo, T. Japanese Patent 02196720 (1990); Chem. Abstr. 1991, 114, 17585.
30. Matsutani, Y.; Sugawara, T.; Kurobe, H.; Takahashi, J.; Moriguchi, Y.; Endo, T. Japanese Patent 02196720 (1990); Chem. Abstr. 1991, 114, 17585.
31. Ameyama, M.; Adachi, O. European Patent 174155 (1986); Chem. Abstr. 1986, 104, 205512.
32. Ameyama, M.; Adachi, O. European Patent 174155 (1986); Chem. Abstr. 1986, 104, 205512.
33. Horiuchi, T.; Horiuchi, H. Japanese Patent 03112912 (1991); Chem. Abstr. 1992, 116, 67189.
34. Horiuchi, T.; Horiuchi, H. Japanese Patent 03112912 (1991); Chem. Abstr. 1992, 116, 67189.
35. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 6348215 (1988); Chem. Abstr. 1989, 110, 82492.
36. Katsumata, M.; Osawa, Y.; Nakagiri, T.; Uchikuga, S. Japanese Patent 6348215 (1988); Chem. Abstr. 1989, 110, 82492.
37. Janes, S. M.; Mu, D.; Wemmer, D.; Smith, A. J.; Kaur, S.; Maltby, D.; Burlingame, A. L.; Klinman, J. P. Science 1990, 248, 9817.
38. Zhang, Z., Tillekeratne, L. M. V. and Hudson, R. A. Biochem. Biophys. Res. Commun. 1995, 212, 41.
39. Corey, E. J.; Tramontano, A. J. Am. Chem. Soc. 1981, 103, 5599.
40. Martin, P.; Winkler, T. Helv. Chim. Acta 1994, 77, 111.
41. Itoh, S.; Fukui, Y.; Haranou, S.; Ogino, M.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 4452.
42. Buckingham, J. Dictionary of Organic Compounds; Chapman and Hall: Pennsylvania, 1982, M-00520.
43. Acheson, R. M.; Hunt, P. G.; Littlewood, D. M.; Murrer, B. A.; Rosenberg, H. E. J. Chem. Soc., Perkin Trans. 1 1978, 1117.
44. Leclerc, G.; Marciniak, G.; Decker, N.; Schwartz, J. J. Med. Chem. 1986, 29, 2433.