Chemoenzymatic formation of novel aminocoumarin antibiotics by the enzymes CouN1 and CouN7

Biochemistry

Volumn 46, Issue 28, 2007, Pages 8462-8471

  Fridman, Micha ^b   Balibar, Carl J ^a   Lupoli, Tania ^b   Kahne, Daniel ^b   Walsh, Christopher T ^a   Garneau Tsodikova, Sylvie ^a,c  

^a HARVARD MEDICAL SCHOOL   (United States)

^b HARVARD UNIVERSITY   (United States)

^c UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOCOUMARIN; CHEMOENZYMATIC FORMATION; INHIBITORY CONCENTRATION; NOVOBIOCIN;

BACTERIA; DNA; ENZYME KINETICS; PROTEINS;

ANTIBIOTICS;

ACYLTRANSFERASE; AMINOCOUMARIN DERIVATIVE; ANTIBIOTIC AGENT; CLOROBIOCIN; COENZYME A; COUMAMYCIN A1; GYRASE INHIBITOR; NOVOBIOCIN; PROTEIN COUN1; PROTEIN COUN7; UNCLASSIFIED DRUG;

ARTICLE; ENZYME ANALYSIS; ENZYME SPECIFICITY; ENZYME SUBSTRATE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN DOMAIN;

ACYL COENZYME A; ACYLTRANSFERASES; ANTI-BACTERIAL AGENTS; APOENZYMES; CARRIER PROTEINS; CHROMATOGRAPHY, LIQUID; MASS SPECTROMETRY; NOVOBIOCIN;

BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA;

EID: 34447545711     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi700433v     Document Type: Article

References (27)

1. Gormley, N. A., Orphanides, G., Meyer, A., Cullis, P. M., and Maxwell, A. (1996) The interaction of coumarin antibiotics with fragments of DNA gyrase B protein, Biochemistry 35, 5083-5092.
2. Maxwell, A., and Lawson, D. M. (2003) The ATP-binding site of type II topoisomerases as a target for antibacterial drugs, Curr. Top. Med. Chem. 3, 283-303.
3. Kampranis, S. C., Gormley, N. A., Tranter, R., Orphanides, G., and Maxwell, A. (1999) Probing the binding of coumarins and cyclothilidines to DNA gyrase, Biochemistry 38, 1967-1976.
4. Drlica, K., and Zhao, X. (1997) DNA gyrase, topoisomerase IV, and the 4-quinolones, Microbiol. Mol. Biol. Rev. 61, 377-392.
5. Munoz, R., and De La Campa, A. G. (1996) ParC subunit of DNA topoisomerase IV of Streptococcus pnewmoniae is the primary target of fluoroquinolones and cooperates with DNA gyrase A subunit in forming resistance phenotype, Antimicrob. Agents Chemother. 40, 2252-2257.
6. Downes, C. S., Ord, M. J., Mullinger, A. M., Collins, A. R., and Johnson, R. T. (1985) Novobiocin inhibition of DNA excision repair may occur through effects on mitochondrial structure and ATP metabolism, not on repair topoisomerases, Carcinogenesis 6, 1343-1352.
7. Martin, M. A. (1994) Methicillin-resistant Staphylococcus aureus: The persistent resistant nosocomial pathogen, Curr. Clin. Top. Infect. Dis. 14, 170-191.
8. Steffensky, M., Muhlenweg, A., Wang, Z.-X., Li, S.-M., and Heide, L. (2000) Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891, Antimicrob. Agents Chemother. 44, 1214-1222.
9. Pojer, F., Li, S.-M., and Heide, L. (2002) Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: New insights into the biosynthesis of aminocoumarin antibiotics, Microbiology 148, 3901-3911.
10. Wang, Z.-X., Li, S.-M., and Heide, L. (2000) Identification of the coumermycin A1 biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489, Antimicrob. Agents Chemother. 44, 3040-3048.
11. Hooper, D. C., Wolfson, J. S., McHugh, G. L., Winters, M. B., and Swartz, M. N. (1982) Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth, Antimicrob. Agents Chemother. 22, 662-671.
12. Garneau, S., Dorrestein, P. C., Kelleher, N. L., and Walsh, C. T. (2005) Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis, Biochemistry 44, 2770-2780.
13. 1, Biochemistry 45, 8568-8578.
14. Quadri, L. E. N., Weinreb, P. H., Lei, M., Nakano, M. M., Zuber, P., and Walsh, C. T. (1998) Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases, Biochemistry 37, 1585-1595.
15. Dorrestein, P. C., Yeh, E., Garneau-Tsodikova, S., Kelleher, N. L., and Walsh, C. T. (2005) Dichlorination of a pyrrolyl-5-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis, Proc. Nat. Acad. Sci. USA. 102, 13843-13848.
16. Freitag, A., Wemakor, E., Li, S.-M., and Heide, L. (2005) Acyl transfer in clorobiocin biosynthesis: Involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar, ChemBioChem 6, 2316-2325.
17. Galm, U., Heller, S., Shapiro, S., Page, M., Li, S.-M., and Heide, L. (2004) Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis, Antimicrob. Agents Chemother. 48, 1307-1312.
18. Sasaki, T., Igarashi, Y., Saito, N., and Furumai, T. (2001) TPU-0031-A and B, new antibiotics of the novobiocin group produced by Streptomyces sp. TP-A0556, J. Antibiot. 54, 441-447.
19. Hinman, J. W., Caron, E. L., and Hoeksema, H. (1957) Novobiocin. V. Carbanoyl migration and isonovobiocin, J. Am. Chem. Soc. 79, 5321-5322.
20. Lewis, R. J., Singh, O. M., Smith, C. V., Skarzynski, T., Maxwell, A., Wonacott, A. J., and Wigley, D. B. (1996) The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography, EMBO J. 15, 1412-1420.
21. Freel Meyers, C. L., Oberthür, M., Xu, H., Heide, L., Kahne, D., and Walsh, C. T. (2004) Characterization of NovP and NovN: Completion of Novobiocin Biosynthesis by Sequential Tailoring of the Noviosyl Ring, Angew. Chem., Int. Ed. 43, 67-70.
22. Xu, H., Heide, L., and Li, S.-M. (2004) New Aminocoumarin Antibiotics Formed by a Combined Mutational and Chemoenzymatic Approach Utilizing the Carbamoyltransferase NovN, Chem. Biol. 11, 655-662.
23. Garneau-Tsodikova, S., Stapon, A., Kahne, D., and Walsh, C. T. (2006) Installation of the pyrrolyl-2-carboxyl pharmacophore by CouN1 and CouN7 in the late biosynthetic steps of the aminocoumarin antibiotics clorobiocin and coumermycin A1, Biochemistry 45, 8568-8578.
24. Liu, F., Garneau, S., and Walsh, C. T. (2004) Hybrid Nonribosomal Peptide-Polyketide Interfaces in Epothilone Biosynthesis: Minimal Requirements at N and C Termini of EpoB for Elongation, Chem. Biol. 11, 1533-1542.
25. O'Connor, S. E., Walsh, C. T., and Liu, F. (2003) Biosynthesis of Epothilone Intermediates with Alternate Starter Units: Engineering Polyketide-Nonribosomal Interfaces, Angew. Chem., Int. Ed. 42, 3917-3921.
26. Galm, U., Schimana, J., Fiedler, H. P., Schmidt, J., Li, S.-M., and Heide, L. (2002) Cloning and analysis of the simocyclinone biosynthetic gene cluster of Streptomyces antibioticus Tu 6040, Arch. Microbiol. 178, 102-114.
27. Ruiz, N., Falcone, B., Kahne, D., and Silhavy, T. J. (2005) Chemical conditionality: A genetic strategy to probe organelle assembly, Cell 121, 307-317.