Characterization of the terminal activation step catalyzed by oxygenase CmmOIV of the chromomycin biosynthetic pathway from streptomyces griseus

Biochemistry

Volumn 50, Issue 8, 2011, Pages 1421-1428

  Bosserman, Mary A ^a   Flórez, Ana B ^b   Shaaban, Khaled A ^a   Braña, Alfredo F ^b   Salas, Jose A ^b   Méndez, Carmen ^b   Rohr, Jürgen ^a  

^a University of Kentucky   (United States)

^b DEPARTAMENTO DE BIOQUÍMICA Y BIOLOGÍA MOLECULAR   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION STEPS; BIOSYNTHETIC PATHWAY; CHROMOMYCIN A; O-METHYLATION; OXYGENASES; STREPTOMYCES GRISEUS;

ACETYLATION; BIOCHEMISTRY; SUGARS;

BIOSYNTHESIS;

CHROMOMYCIN A3; OXYGENASE; PRODRUG; PROTEIN CMMOIV; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INACTIVATION; METHYLATION; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STREPTOMYCES GRISEUS;

BIOCATALYSIS; CHROMOMYCIN A3; ENZYME ACTIVATION; KINETICS; MUTATION; OXYGENASES; STREPTOMYCES GRISEUS; SUBSTRATE SPECIFICITY;

STREPTOMYCES GRISEUS;

EID: 79951892996     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi1016205     Document Type: Article

References (32)

1. Skarbek, J. D. and Speedie, M. K. (1981) Antitumor antibiotics of the aureolic acid group: Chromomycin A3, mithramycin A, and olivomycin A. In Antitumor compounds of natural origin: Chemistry and biochemistry (Aszalos, A., Ed.) pp 191 - 235, CRC Press, Boca Raton, FL.
2. Lombó, F., Menendez, N., Salas, J. A., and Méndez, C. (2006) The aureolic acid family of antitumor compounds: Structure, mode of action, biosynthesis, and novel derivatives Appl. Microbiol. Biotechnol. 73, 1-14
3. 3 and Mithramycin with Poly(dG-dC)·Poly(dC-dG) and Poly(dG)·Poly(dC) Biochemistry 36, 2291-2299
4. 2+-dimer complex Biochemistry 32, 463-471
5. Jayasuriya, H., Lingham, R. B., Graham, P., Quamina, D., Herranz, L., Genilloud, O., Gagliardi, M., Danzeisen, R., Tomassini, J. E., Zink, D. L., Guan, Z. Q., and Singh, S. B. (2002) Durhamycin A, a potent inhibitor of HIV Tat transactivation J. Nat. Prod. 65, 1091-1095
6. Bianchi, N., Osti, F., Rutigliano, C., Corradini, F. G., Borsetti, E., Tomassetti, M., Mischiati, C., Feriotto, G., and Gambari, R. (1999) The DNA-binding drugs mithramycin and chromomycin are powerful inducers of erythroid differentiation of human K562 cells Br. J. Haematol. 104, 258-265
7. Devi, P. G., Chakraborty, P. K., and Dasgupta, D. (2009) Inhibition of a Zn(II)-containing enzyme, alcohol dehydrogenase, by anticancer antibiotics, mithramycin and chromomycin A3 J. Biol. Inorg. Chem. 14, 347-359
8. Menéndez, N., Nur-e-Alam, M., Braña, A. F., Rohr, J., Salas, J. A., and Méndez, C. (2004) Tailoring modification of deoxysugars during biosynthesis of the antitumour drug chromomycin A by Streptomyces griseus ssp. griseus Mol. Microbiol. 53, 903-915
9. Menéndez, N., Nur-e-Alam, M., Braña, A. F., Rohr, J., Salas, J. A., and Méndez, C. (2004) Biosynthesis of the antitumor chromomycin A3 in Streptomyces griseus: Analysis of the gene cluster and rational design of novel chromomycin analogs Chem. Biol. 11, 21-32
10. Menéndez, N., Nur-e-Alam, M., Fischer, C., Braña, A. F., Salas, J. A., Rohr, J., and Méndez, C. (2006) Deoxysugar Transfer during Chromomycin A3 Biosynthesis in Streptomyces griseus subsp. griseus: New Derivatives with Antitumor Activity Appl. Environ. Microbiol. 72, 167-177
11. Montanari, A. and Rosazza, J. P. (1990) Biogenesis of chromomycin A3 by Streptomyces griseus J. Antibiot. 43, 883-889
12. 2+ complex Biochem. Biophys. Res. Commun. 173, 689-696
13. Majee, S., Dasgupta, D., and Chakrabarti, A. (1999) Interaction of the DNA-binding antitumor antibiotics, chromomycin and mithramycin with erythroid spectrin Eur. J. Biochem. 260, 619-626
14. Mir, M. A., Majee, S., Das, S., and Dasgupta, D. (2003) Association of chromatin with anticancer antibiotics, mithramycin and chromomycin A3 Bioorg. Med. Chem. 11, 2791-2801
15. 2+ Complex in Methanol: Role of the Carbohydrates in Complex Formation J. Am. Chem. Soc. 115, 7962-7970
16. Mir, M. A. and Dasgupta, D. (2001) Association of the Anticancer Antibiotic Chromomycin A3 with the Nucleosome: Role of Core Histone Tail Domains in the Binding Process Biochemistry 40, 11578-11585
17. 2. Evidence that the saccharide chains have a role in sequence specificity J. Mol. Biol. 231, 753-767
18. 2 complex: Evidence for an interaction between the E saccharides Biopolymers 54, 104-114
19. 2 complex reveals GGCC binding specificity of the drug dimer chelated by a metal ion Nucleic Acids Res. 32, 2214-2222
20. Hou, M. H., Lu, W. J., Lin, H. Y., and Yuann, J. M. (2008) Studies of sequence-specific DNA binding, DNA cleavage, and topoisomerase I inhibition by the dimeric chromomycin A3 complexed with Fe(II) Biochemistry 47, 5493-5502
21. Gao, X. and Patel, D. J. (1989) Solution structure of the chromomycin-DNA complex Biochemistry 28, 751-762
22. 2: Role of Sugars in Antibiotic-DNA Recognition J. Phys. Chem. B 106, 6947-6953
23. 3, and mithramycin: Roles of minor groove width and ligand flexibility Biopolymers 56, 85-95
24. 2 Indian J. Biochem. Biophys. 38, 64-70
25. 2+ Biopolymers 62, 131-140
26. Menéndez, N., Brana, A. F., Salas, J. A., and Mendez, C. (2007) Involvement of a chromomycin ABC transporter system in secretion of a deacetylated precursor during chromomycin biosynthesis Microbiology 153, 3061-3070
27. Beam, M. P., Bosserman, M. A., Noinaj, N., Wehenkel, M., and Rohr, J. (2009) Crystal structure of Baeyer-Villiger monooxygenase MtmOIV, the key enzyme of the mithramycin biosynthetic pathway Biochemistry 48, 4476-4487
28. Fernandez-Lozano, M. J., Remsing, L. L., Quiros, L. M., Braña, A. F., Fernandez, E., Sanchez, C., Méndez, C., Rohr, J., and Salas, J. A. (2000) Characterization of two polyketide methyltransferases involved in the biosynthesis of the antitumor drug mithramycin by Streptomyces argillaceus J. Biol. Chem. 275, 3065-3074
29. Olano, C., Gómez, C., Pérez, M., Palomino, M., Pineda-Lucena, A., Carbajo, R. J., Braña, A. F., Méndez, C., and Salas, J. A. (2009) Deciphering biosynthesis of the RNA polymerase inhibitor streptolydigin and generation of glycosylated derivatives Chem. Biol. 16, 1031-1044
30. Prado, L., Fernandez, E., Weissbach, U., Blanco, G., Quiros, L. M., Brana, A. F., Méndez, C., Rohr, J., and Salas, J. A. (1999) Oxidative cleavage of premithramycin B is one of the last steps in the biosynthesis of the antitumor drug mithramycin Chem. Biol. 6, 19-30
31. Rodriguez, D., Quiros, L. M., Braña, A. F., and Salas, J. A. (2003) Purification and characterization of a monooxygenase involved in the biosynthetic pathway of the antitumor drug mithramycin J. Bacteriol. 185, 3962-3965
32. Gibson, M., Nur-e-Alam, M., Lipata, F., Oliveira, M. A., and Rohr, J. (2005) Characterization of Kinetics and Products of the Baeyer-Villiger Oxygenase MtmOIV, the Key Enzyme of the Biosynthetic Pathway toward the Natural Product Anticancer Drug Mithramycin from Streptomyces argillaceus J. Am. Chem. Soc. 127, 17594-17595