Synthesis and characterization of model compounds of the lysine tyrosyl quinone cofactor of lysyl oxidase

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6113-6125

  Mure, Minae ^a   Wang, Sophie X ^a   Klinman, Judith P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH EFFECTS; SYNTHESIS (CHEMICAL); TITRATION;

NUCLEOPHILIC ADDITIONS;

ORGANIC COMPOUNDS;

2,4,5 TRIHYDROXYPHENYLALANINE QUINONE; 3 N BUTYLAMINO 5 ETHYL 1,2 BENZOQUINONE; 4 ETHYL 1,2 BENZOQUINONE; 4 N BUTYLAMINO 5 ETHYL 1,2 BENZOQUINONE; AMINE; BUTYLAMINE; LYSINE DERIVATIVE; LYSINE TYROSYL QUINONE COFACTOR; PHENYLHYDRAZINE; PROTEIN LYSINE 6 OXIDASE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ADDITION REACTION; ARTICLE; BIOGENESIS; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PH; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

BENZOQUINONES; BIOMIMETIC MATERIALS; BUTYLAMINES; ELECTROCHEMISTRY; HYDROGEN-ION CONCENTRATION; KINETICS; LYSINE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENOLS; PHENYLHYDRAZINES; PROTEIN-LYSINE 6-OXIDASE; QUINONES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0037613389     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0214274     Document Type: Article

References (67)

1. Csiszar, K. Prog. Nucleic Acid Res. Mol. Biol. 2001, 70, 1-32.
2. Rucker, R. B.; Kosonen, T.; Clegg, M. S.; Mitchell, A. E.; Rucker, B. R.; UriuHare, J. Y.; Keen, C. L. Am. J. Clin. Nutr. 1998, 67, S996-S1002.
3. SmithMungo, L. I.; Kagan, H. M. Matrix Biol. 1998, 16, 387-398.
4. Kagan, H. M. Pathol. Res. Pract. 1994, 190, 910-919.
5. Streichenberger, N.; Peyrol, S.; Philit, F.; Loire, R.; Sommer, P.; Cordier, J. F. Virchows. Arch. 2001, 439, 78-84.
6. Kagan, H. M.; Williams, M. A.; Williamson, P. R.; Anderson, J. M. J. Biol. Chem. 1984, 259, 11203-11207.
7. Ohkawa, K.; Fujii, K.; Nishida, A.; Yamauchi, T.; Ishibashi, H.; Yamamoto, H. Biomacromolecules 2001, 2, 773-779.
8. Butler, E.; Handlin, J.; Benson, S. Exp. Cell Res. 1987, 173, 174-182.
9. Kenyon, K.; Contente, S.; Trackman, P. C.; Tang, J.; Kagan, H. M.; Friedman, R. M. Science 1991. 253, 802.
10. Hajnal, A.; Klemenz, R.; Schafer, R. Cancer Res. 1993, 53, 4670-4675.
11. Oberhuber, H.; Seliger, B.; Schafer, R. Mol. Carcinog. 1995, 12, 198-204.
12. Peyrol, S.; Raccurt, M.; Gerard, F.; Gleyzal, C.; Grimaud, J. A.; Sommer, P. Am. J. Pathol. 1997, 150, 497-507.
13. Ren, C. Z.; Yang, G.; Timme, T. L.; Wheeler, T. M.; Thompson, T. C. Cancer Res. 1998, 58, 1285-1290.
14. Csiszar, K.; Entersz, I.; Trackman, P. C.; Samid, D.; Boyd, C. D. Mol. Biol. Rep. 1996, 23, 97-108.
15. Li, W. D.; Liu, G. M.; Chou, I. N.; Kagan, H. M. J. Cell. Biochem. 2000, 78, 550-557.
16. Ito, H.; Akiyama, H.; Iguchi, H.; Iyama, K.; Miyamoto, M.; Ohsawa, K.; Nakamura, T. J. Biol. Chem. 2001, 276, 24023-24029.
17. Omori, K.; Fujiseki, Y.; Suzukawa, J.; Inagaki, C. Matrix Biol. 2002, 21, 337-348.
18. McIntire, W. S.; Hartmann, C. In Principles and applications of quinoproteins; Davidson, V. L., Ed.; Dekker: New York, 1993; pp 97-171.
19. Knowles, P. F.; Dooley, D. M. In Metal ions in biological systems; Sigel, H., Sigel, A., Eds.; Dekker: New York, 1994; Vol. 30, pp 360-403.
20. Klinman, J. P.; Mu, D. Annu. Rev. Biochem. 1994, 63, 299-344.
21. Jalkanen, S.; Salmi, M. EMBO J. 2001, 20, 3893-3901.
22. Mure, M.; Mills, S. A.; Klinman, J. P. Biochemistry 2002, 41, 9269-9278.
23. Gacheru, S. N.; Trackman, P. C.; Shah, M. A.; Ogara, C. Y.; Spacciapoli, P.; Greenaway, F. T.; Kagan, H. M. J. Biol. Chem. 1990, 265, 19022-19027.
24. Iguchi, H.; Sano, S. Connect. Tissue Res. 1985, 14, 129-139.
25. Williamson, P. R.; Moog, R. S.; Dooley, D. M.; Kagan, H. M. J. Biol. Chem. 1986, 261, 16302-16305.
26. Janes, S. M.; Mu, D.; Wemmer, D.; Smith, A. J.; Kaur, S.; Maltby, D.; Burlingame, A. L.; Klinman, J. P. Science 1990, 248, 981-987.
27. Wang, S. X.; Mure, M.; Medzihradszky, K. F.; Burlingame, A. L.; Brown, D. E.; Dooley, D. M.; Smith, A. J.; Kagan, H. M.; Klinman, J. P. Science 1996, 273, 1078-1084.
28. McIntire, W. S.; Wemmer, D. E.; Chistoserdov, A.; Lidstrom, M. E. Science 1991, 252, 817-824.
29. Datta, S.; Mori, Y.; Takagi, K.; Kawaguchi, K.; Chen, Z. W.; Okajima, T.; Kuroda, S.; Ikeda, T.; Kano, K.; Tanizawa, K.; Mathews, F. S. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14268-14273.
30. Vandenberghe, I.; Kim, J. K.; Devreese, B.; Hacisalihoglu, A.; Iwabuki, H.; Okajima, T.; Kuroda, S.; Adachi, O.; Jongejan, J. A.; Duine, J. A.; Tanizawa, K.; Van Beeumen, J. J. Biol. Chem. 2001, 276, 42923-42931.
31. Satoh, A.; Kim, J. K.; Miyahara, I.; Devreese, B.; Vandenberghe, I.; Hacisalihoglu, A.; Okajima, T.; Kuroda, S.; Adachi, O.; Duine, J. A.; Van Beeumen, J.; Tanizawa, K.; Hirotsu, K. J. Biol. Chem. 2002, 277, 2830-2834.
32. Schwartz, B.; Klinman, J. P. Vitam. Horm. 2001, 61, 219-239.
33. Klinman, J. P. J. Biol. Chem. 1996, 271, 27189-27192.
34. Dooley, D. M. J. Biol. Inorg. Chem. 1999, 4, 1-11.
35. Kim, M.; Okajima, T.; Kishishita, S.; Yoshimura, M.; Kawamori, A.; Tanizawa, K.; Yamaguchi, H. Nat. Struct. Biol. 2002, 9, 591-596.
36. Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1993, 115, 7117-7127.
37. Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1995, 117, 8698-8706.
38. Mure, M.; Klinman, J. P. J. Am. Chem. Soc. 1995, 117, 8707-8718.
39. Mure, M.; Klinman, J. P. Methods Enzymol. 1995, 258, 39-52.
40. Lee, Y.; Sayre, L. M. J. Am. Chem. Soc. 1995, 117, 11823-11828.
41. Lee, Y. H.; Sayre, L. M. J. Am. Chem. Soc. 1995, 117, 3096-3105.
42. Lee, Y. H.; Huang, H.; Sayre, L. M. J. Am. Chem. Soc. 1996, 118, 7241-7242.
43. Leem, J. Y.; Nishimura, C.; Kurata, S.; Shimada, I.; Kobayashi, A.; Natori, S. J. Biol. Chem. 1996, 271, 13573-13577.
44. Xu, R. D.; Huang, X.; Hopkins, T. L.; Kramer, K. J. Insect Biochem. Mol. Biol. 1997, 27, 101-108.
45. Kramer, K. J.; Kanost, M. R.; Hopkins, T. L.; Jiang, H. B.; Zhu, Y. C.; Xu, R. D.; Kerwin, J. L.; Turecek, F. Tetrahedron 2001, 57. 385-392.
46. Montine, T. J.; Farris, D. B.; Graham, D. G. J. Neuropathol. Exp. Neurol. 1995, 54, 311-319.
47. Hastings, T. G.; Zigmond, M. J. J. Neurochem. 1994, 63, 1126-1132.
48. Wang, S. X.; Nakamura, N.; Mure, M.; Klinman, J. P.; SandersLoehr, J. J. Biol. Chem. 1997, 272, 28841-28844.
49. Ling, K. Q.; Kim, J.; Sayre, L. M. J. Am. Chem. Soc. 2001, 123, 9606-9611.
50. Akagawa, M.; Suyama, K. Biochem. Biophys. Res. Commun. 2001, 281, 193-199.
51. Vitale, A. A.; Chiocconi, A. A. J. Chem. Res., Suppl. 1996, 336-337.
52. Moenneloccoz, P.; Nakamura, N.; Steinebach, V.; Duine, J. A.; Mure, M.; Klinman, J. P.; Sandersloehr, J. Biochemistry 1995, 34, 7020-7026.
53. Gacheru, S. N.; Trackman, P. C.; Kagan, H. M. J. Biol. Chem. 1988, 263, 16704-16708.
54. Janes, S. M.; Palcic, M. M.; Scaman, C. H.; Smith, A. J.; Brown, D. E.; Dooley, D. M.; Mure, M.; Klinman, J. P. Biochemistry 1992, 31, 12147-12154.
55. Schwartz, B.; Olgin, A. K.; Klinman, J. P. Biochemistry 2001, 40, 2954-2963.
56. Waite, J. H. Comp. Biochem. Physiol. B 1990, 97, 19-29.
57. Burzio, L. A.; Waite, J. H. Biochemistry 2000, 39, 11147-11153.
58. Sugumaran, M. Bioorg. Chem. 1987, 15, 194.
59. Akiyama, N.; Hijikata, M.; Kobayashi, A.; Yamori, T.; Tsuruo, T.; Natori, S. Anticancer Res. 2000, 20, 357-362.
60. Christensen, A. M.; Schaefer, J.; Kramer, K. J.; Morgan, T. D.; Hopkins, T. L. J. Am. Chem. Soc. 1991, 113, 6799-6802.
61. Mason, H. S.; Peterson, E. W. Biochim. Biophys. Acta 1965, 111, 134-146.
62. Rzepecki, L. M.; Waite, J. H. Anal. Biochem. 1989, 179, 375-381.
63. Chen, Z.; Schwartz, B.; Williams, N. K.; Li, R.; Klinman, J. P.; Mathews, F. S. Biochemistry 2000, 39, 9709-9717.
64. Matsuzaki, R.; Fukui, T.; Sato, H.; Ozaki, Y.; Tanizawa, K. FEBS Lett. 1994, 351, 360-364.
65. Cai, D. Y.; Klinman, J. P. J. Biol. Chem. 1994, 269, 32039-32042.
66. Schwartz, B.; Dove, J. E.; Klinman, J. P. Biochemistry 2000, 39, 3699-3707.
67. Mandal, S.; Lee, Y.; Purdy, M. M.; Sayre, L. M. J. Am. Chem. Soc. 2000, 122, 3574-3584.