Hydroxyquinone O-methylation in mitomycin biosynthesis

Journal of the American Chemical Society

Volumn 129, Issue 20, 2007, Pages 6470-6476

  Grüschow, Sabine ^a   Chang, Leng Chee ^a,b   Mao, Yingqing ^a,c   Sherman, David H ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MINNESOTA DULUTH   (United States)

^c RayBiotech   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOGENESIS; DNA-ALKYLATING AGENTS; MITOMYCINS;

BIOSYNTHESIS; CATALYSIS; DRUG THERAPY; ELECTROCHEMISTRY; ENZYME ACTIVITY;

ANTIBIOTICS;

7 NORMITOMYCIN A; 7 NORMITOMYCIN B; ALKYLATING AGENT; METHYLTRANSFERASE; MITOMYCIN; MITOMYCIN A; MITOMYCIN B; MITOMYCIN C; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BACTERIUM MUTANT; CATALYSIS; CULTURE MEDIUM; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; GENE DELETION; GENE OVEREXPRESSION; METHYLATION; MMCR GENE; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; SOLID TUMOR; STREPTOMYCES LAVENDULAE;

CATALYSIS; METHYLATION; METHYLTRANSFERASES; MITOMYCINS; MOLECULAR STRUCTURE; MUTATION; STREPTOMYCES;

EID: 34249002384     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0700193     Document Type: Article

References (49)

1. Bradner, W. T. Cancer Treat. Rev. 2001, 27, 35-50.
2. Tomasz, M. Chem. Biol. 1995, 2, 575-579.
3. Rao, G. M.; Lown, J. W.; Plambeck, J. A. J. Electrochem. Soc. 1977, 124, 195-198.
4. Rao, G. M.; Begleiter, A.; Lown, J. W.; Plambeck, J. A. J. Electrochem. Soc 1977, 124, 199-202.
5. Claridge, C. A.; Bush, J. A.; Doyle, T. W.; Nettleton, D. E.; Moseley, J. E.; Kimball, D.; Kammer, M. F.; Veitch, J. J. Antibiot. 1986, 39, 437-446.
6. Sami, S. M.; Iyengar, B. S.; Tarnow, S. E.; Remers, W. A.; Bradner, W. T.; Schurig, J. E. J. Med. Chem. 1984, 27, 701-708.
7. Arai, H.; Kanda, Y.; Ashizawa, T.; Morimoto, M.; Gomi, K.; Kono, M.; Kasai, M. J. Med. Chem. 1994, 37, 1794-1804.
8. Iyengar, B. S.; Sami, S. M.; Remers, W. A.; Bradner, W. T.; Schurig, J. E. J. Med. Chem. 1983, 26, 16-20.
9. Mao, Y. Q.; Varoglu, M.; Sherman, D. H. Chem. Biol. 1999, 6, 251-263.
10. Hornemann, U.; Kehrer, J. P.; Nunez, C. S.: Ranieri, R. L. J. Am. Chem. Soc. 1974, 96, 320-322.
11. Anderson, M. G.; Kibby, J. J.; Rickards, R. W.; Rothschild, J. M. J. Chem. Soc, Chem. Commun. 1980, 1277-1278.
12. Kim, C. G.; Yu, T. W.; Fryhle, C. B.; Handa, S.; Floss, H. G. J. Biol. Chem. 1998, 273, 6030-6040.
13. August, P. R.; Tang, L.; Yoon, Y. J.; Ning, S.; Müller, R.; Yu, T. W.; Taylor, M.; Hoffmann, D.; Kim, C. G.; Zhang, X. H.; Hutchinson, C. R.; Floss, H. G. Chem. Biol. 1998, 5, 69-79.
14. Yu, T. W.; Bai, L. Q.; Clade, D.; Hoffmann, D.; Toelzer. S.; Trinh, K. Q.; Xu, J.; Moss, S. J.; Leistner, E.; Floss. H. G. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7968-7973.
15. Yu, T. W.; Müller, R.; Müller, M.; Zhang, X. H.; Draeger, G.; Kim, C. G.; Leistner, E.; Floss, H. G. J. Biol. Chem. 2001, 276, 12546-12555.
16. Guo, J. T.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 10642-10643.
17. Arakawa, K.: Müller, R.; Mahmud, T.; Yu, T. W.; Floss, H. G. J. Am. Chem. Soc. 2002, 124, 10644-10645.
18. Guo, J. T.; Frost, J. W. J. Am. Chem. Soc. 2002, 124, 528-529.
19. Eads, J. C; Beeby, M.; Scapin, G.; Yu, T. W.; Floss, H. G. Biochemistry 1999, 38, 9840-9849.
20. Rickards, R. W.; Rukachaisirikul, V. Aust. J. Chem. 1987, 40, 1011-1015.
21. Kirsch, E. J.; Korshalla, J. D. J. Bacteriol. 1964, 87, 247-255.
22. Bezanson, G. S.; Vining, L. C. Can. J. Biochem. 1971, 49, 911-918.
23. Hornemann, U; Cloyd, J. C. J. Chem. Soc, Chem. Commun. 1971, 301-302.
24. Hornemann, U.; Eggert, J. H. J. Antibiot. 1975, 28, 841-843.
25. Wakaki. K.: Huromo, H.; Tomioka, K.; Shimizu, G.; Kato, E.: Kamada, H.; Kudo, S.; Fujimoto, Y. Antibiot. Chemother. 1958. 8, 228-240.
26. Sheldon, P. J.; Johnson, D. A.; August, P. R.; Liu, H. W.; Sherman, D. H. J. Bacteriol. 1997, 179, 1796-1804.
27. Martin, T. W.; Dauter, Z.; Devedjiev, Y.; Sheffield. P.; Jelen, F.; He, M.; Sherman, D. H.; Otlewski, J.; Derewenda, Z. S.; Derewenda, U. Structure 2002, 10, 933-942.
28. August, P. R.; Rahn, J. A.; Flickinger, M. C; Sherman. D. H. Gene 1996, 175, 261-267.
29. Belcourt. M. F.; Penketh, P. G.; Hodnick, W. F.; Johnson, D. A.; Sherman, D. H.; Rockwell. S.: Sartorelli, A. C. Proc. Natl. Acad. Sci. U.S.A. 1999. 96, 10489-10494.
30. Varoglu, M.; Mao, Y. Q.; Sherman, D. H. J. Am. Chem. Soc. 2001, 123, 6712-6713.
31. Nishikohri, K.; Fukui, S. Eur. J. Appl. Microbiol. 1975, 1, 129-145.
32. Sambrook, J.; Russel, D. W. Molecular Cloning - A Laboratory Manual, 3rd ed.; Cold Spring Harbor Laboratory Press: Woodbury, NY, 2001
33. Denis, F.; Brzezinski, R. Gene 1992, 111, 115-118.
34. Bierman, M.; Logan, R.; O'Brien, K.; Seno, E. T.; Rao, R. N.; Schoner B. E. Gene 1992, 116, 43-49.
35. Mao, Y. Q.; Varoglu, M.; Sherman, D. H. J. Bacteriol. 1999. 181, 2199-2208.
36. Baltz, R. H. Dev. Ind. Microbiol. 1980, 21, 43-54.
37. Mazodier, P.; Petter, R.; Thompson. C. J. Bacteriol. 1989, 171, 3583-3585.
38. Garrett, E. R. J. Med. Chem. 1963, 6, 488-501.
39. Beijnen, J. H.; Denhartigh, J.; Underberg, W. J. M. J. Pharm. Biomed. Anal. 1985, 3, 59-69.
40. Kono, M.; Saitoh, Y.; Shirhata, K.; Arai, Y.; Ishii, S. J. Am. Chem Soc 1987, 109, 7224-7225.
41. Beijnen, J. H.; Lingeman, H.; van Munster, H. A.; Underberg W. J. J. Pharm. Biomed. Anal. 1986, 4, 275-295.
42. Shafiee, A.; Motamedi, H.; Chen, T. Eur. J. Biochem. 1994, 225, 755-764.
43. Kreuzman, A. J.; Turner, J. R.; Yeh, W. K. J. Biol. Chem. 1988, 263, 15626-15633.
44. Ibdah, M.; Zhang, X. H.; Schmidt, J.; Vogt, T. J. Biol. Chem. 2003. 278, 43961-43972.
45. Xu, J.; Mahmud, T.; Floss, H. G. Arch. Biochem. Biophys. 2003, 411, 277-288.
46. Freel Meyers, C. L.; Oberthur, M.; Xu, H.; Heide, L.; Kahne, D.; Walsh, C. T. Angew. Chem.. Int. Ed. 2004, 43, 67-70.
47. Lavid, N.; Wang, J.; Shalit, M.; Guterman, I.; Bar, E.; Beuerle, T.; Menda, N.; Shafir, S.; Zamir, D.; Adam, Z.; Vainstein, A.; Weiss, D.; Pichersky, E.; Lewinsohn, E. Plant Physiol. 2002, 129, 1899-1907.
48. Pacholec, M.; Tao, J.; Walsh, C. T. Biochemistry 2005, 44, 14969-14976
49. Wang, J.; Pichersky, E. Arch. Biochem. Biophys. 1999, 368, 172-180.