A model compound of the novel organic cofactor CTQ (cysteine tryptophylquinone) of quinohemoprotein amine dehydrogenase

European Journal of Organic Chemistry

Volumn , Issue 14, 2004, Pages 3074-3079

  Murakami, Yoko ^a   Tachi, Yoshimitsu ^a   Itoh, Shinobu ^a  

^a Osaka City University   (Japan)

Author keywords

Amine dehydrogenases; Cofactors; Post translational modification; Quinones; Quinoprotein

Indexed keywords

BENZENE DERIVATIVE; CYSTEINE DERIVATIVE; INDOLE DERIVATIVE; OXIDOREDUCTASE; SULFIDE;

ARTICLE; INFRARED SPECTROSCOPY; MICHAEL ADDITION; OXIDATION REDUCTION REACTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

EID: 4544255691     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400191     Document Type: Article

References (22)

1. O. Adachi, T. Kubota, A. Hacisalihoglu, H. Toyama, E. Shinagawa, J. A. Duine, K. Matsushita, Biosci. Biotechnol. Biochem. 1998, 62, 469-478.
2. K. Takagi, M. Torimura, K. Kawaguchi, K. Kano, T. Ikeda, Biochemistry 1999, 38, 6935-6942.
3. S. Datta, Y. Mori, K. Takagi, K. Kawaguchi, Z.-W. Chen, T. Okajima, S. Kuroda, T. Ikeda, K. Kano, K. Tanizawa, F. S. Mathews, Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 14268-14273.
4. A. Satoh, J.-K. Kim, I. Miyahara, B. Devreese, I. Vandenberghe, A. Hacisalihoglu, T. Okajima, S. Kuroda, O. Adachi, J. A. Duine, J. Van Beeumen, K. Tanizawa, K. Hirotsu, J. Biol. Chem. 2002, 277, 2830-2834.
5. S. M. Janes, D. Mu, D. Wemmer, A. J. Smith, S. Kaur, D. Maltby, A. L. Burlingame, J. P. Klinman, Science 1990, 248, 981-987.
6. S. X. Wang, M. Mure, K. F. Medzihradszky, A. L. Burlingame, D. E. Brown, D. M. Dooley, A. J. Smith, H. M. Kagan, J. P. Klinman, Science 1996, 273, 1078-1084.
7. N. Ito, S. E. V. Phillips, C. Stevens, Z. B. Ogel, M. J. McPherson, J. N. Keen, K. D. S. Yadav, P. F. Knowles, Nature 1991, 350, 87-90.
8. W. S. McIntire, D. E. Wemmer, A. Chistoserdov, M. E. Lidstrom, Science 1991, 252, 817-824.
9. D. P. Sun, K. Ono, T. Okajima, K. Tanizawa, M. Uchida, Y. Yamamoto, F. S. Mathews, V. L. Davidson, Biochemistry 2003, 42, 10896-10903.
10. N. Fujieda, M. Mori, K. Kano, T. Ikeda, Biochemistry 2002, 41, 13736-13743.
11. S. Itoh, M. Ogino, M. Komatsu, Y. Ohshiro, J. Am. Chem. Soc. 1992, 114, 7294-7295.
12. S. Itoh, M. Ogino, S. Haranou, T. Terasaka, T. Ando, M. Komatsu, Y. Ohshiro, S. Fukuzumi, K. Kano, K. Takagi, T. Ikeda, J. Am. Chem. Soc. 1995, 117, 1485-1493.
13. F. Benington, R. D. Morin, L. C. Clark Jr., J. Org. Chem. 1959, 24, 917-919.
14. P. Magnus, L. Gazzard, L. Hobson, A. H. Payne, T. J. Rainey, N. Westlund, V. Lynch, Tetrahedron 2002, 58, 3423-3443.
15. Deprotection of the methoxy groups of the non-tosylated derivative 4 under the same experimental conditions gave a complicated mixture of products.
16. 2, while competitive addition of the mercaptan to the C-6 carbonyl carbon atom induces oxidative coupling of the mercaptan to produce quinol 6 and the corresponding disulfide, see: S. Itoh, N. Kato, M. Mure, Y. Ohshiro, Bull. Chem. Soc. Jpn. 1987, 60, 420-422.
17. 2 (the quinol form of 1), but it is easily converted into quinone 1 by air oxidation during work up, see: S. Itoh, Y. Ohshiro, T. Agawa, Bull. Chem. Soc. Jpn. 1986, 59, 1911-1914.
18. R. A. Abramovitch, X. C. Ye, W. T. Pennington, G. Schimek, D. Bogdal, J. Org. Chem. 2000, 65, 343-351.
19. H. Brunner, D. Mijolovic, M. Zabel, Synthesis 2001, 1671-1680.
20. A. R. Pearson, L. H. Jones, L. A. Higgins, A. E. Ashcroft, C. M. Wilmot, V. L. Davidson, Biochemistry 2003, 42, 3224-3230.
21. D. D. Perrin, W. L. F. Armarego, D. R. Perrin, Purification of Laboratory Chemicals, 4th ed., Pergamon Press, Elmsford, New York, 1996.
22. Crystal Structure: Crystal Structure Analysis Package, version 3.5.1, Molecular Structure Corp. and Rigaku Corp., Tokyo, Japan, 2003.