CouO and NovO: C-methyltransferases for tailoring the aminocoumarin scaffold in coumermycin and novobiocin antibiotic biosynthesis

Biochemistry

Volumn 44, Issue 45, 2005, Pages 14969-14976

  Pacholec, Michelle ^a   Tao, Junhua ^b   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; BIOSYNTHESIS; DIMERS; ORGANIC ACIDS; PHENOLS; SUBSTRATES;

PHENOLIC OXYGEN; STREPTOMYCETE;

ENZYMES;

AMIDE; ANTIBIOTIC AGENT; CLOROBIOCIN; COUMAMYCIN; COUMAMYCIN A1; COUMARIN; HYDROXYL GROUP; LIGASE; METHYLTRANSFERASE; NOVOBIOCIC ACID; NOVOBIOCIN; PHENOL DERIVATIVE; PROTEIN COUL; PROTEIN COUO; PROTEIN NOVH; PROTEIN NOVL; PROTEIN NOVM; PROTEIN NOVO; TYROSINE; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; ENZYME PURIFICATION; ESCHERICHIA COLI; GLYCOSYLATION; METHYLATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STREPTOMYCETACEAE;

AMINOCOUMARINS; ANTI-BACTERIAL AGENTS; ESCHERICHIA COLI; KINETICS; METHYLTRANSFERASES; NOVOBIOCIN; STREPTOMYCES;

ESCHERICHIA COLI; STREPTOMYCETACEAE;

EID: 27744564434     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi051599o     Document Type: Article

References (25)

1. Kampranis, S. C., Gormley, N, A., Tranter, R., Orphanides, G., and Maxwell, A. (1999) Probing the binding of coumarins and cyclothialidines to DNA gyrase. Biochemistry 38, 1967-1976.
2. Chatterji, M., Unniraman, S., Maxwell, A., and Nagaraja, V. (2000) The additional 165 amino acids in the B protein of Escherichia coli DNA gyrase have an important role in DNA binding. J. Biol. Chem. 275, 22888-22894.
3. 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.
4. 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.
5. 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.
6. Wang, Z. X., Li, S. M., and Heide, L. (2000) Identification of the coumermycin A(1) biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Antimicrob. Agents Chemother. 44, 3040-3048.
7. Li, S. M., Westrich, L., Schmidt, J., Kuhnt, C., and Heide, L. (2002) Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments. Microbiology 148, 3317-3326.
8. Xu, H., Wang, Z. X., Schmidt, J., Heide, L., and Li, S. M. (2002) Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin. Mol. Genet. Genomics 268, 387-396.
9. Chen, H., and Walsh, C. T. (2001) Coumarin formation in novobiocin biosynthesis: beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI. Chem. Biol. 8, 301-312.
10. Pacholec, M., Hillson, N., and Walsh, C. T. (2005) NovJ/NovK Catalyze Benzylic Oxidation of a β-Hydroxyl Tyrosyl-S-Pantetheinyl Enzyme During Aminocoumarin Ring Formation in Novobiocin Biosynthesis. Biochemistry, in press.
11. Freel Meyers, C. L., Oberthur, M., Anderson, J. W., Kahne, D., and Walsh, C. T. (2003) Initial characterization of novobiocic acid noviosyl transferase activity of NovM in biosynthesis of the antibiotic novobiocin. Biochemistry 42, 4179-4189.
12. Freel Meyers, C. L., Oberthur, 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.
13. Freel Meyers, C. L., Oberthur, M., Heide, L., Kahne, D., and Walsh, C, T. (2004) Assembly of dimeric variants of coumermycins by tandem action of the four biosynthetic enzymes CouL, CouM, CouP, and NovN. Biochemistry 43, 15022-15036.
14. Steffensky, M., Li, S. M., and Heide, L. (2000) Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891. J. Biol. Chem. 275, 21754-21760.
15. Schmutz, E., Steffensky, M., Schmidt, J., Porzel, A., Li, S. M., and Heide, L. (2003) An unusual amide synthetase (CouL) from the coumermycin A1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489. Eur. J. Biochem. 270, 4413-4419.
16. 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.
17. Xu, H., Kahlich, R., Kammerer, B., Heide, L., and Li, S. M. (2003) CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin. Microbiology 149, 2183-2191.
18. Eustaquio, A. S., Gust, B., Luft, T., Li, S. M., Chater, K. F., and Heide, L. (2003) Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs. Chem. Biol. 10, 279-288.
19. Tao, J., Hu, S., Pacholec, M., and Walsh, C. T. (2003) Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway. Org. Lett. 5, 3233-3236.
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. Tsai, F. T., Singh, O. M., Skarzynski, T., Wonacott, A. J., Weston, S., Tucker, A., Pauptit, R. A., Breeze, A. L., Poyser, J. P., O'Brien, R., Ladbury, J. E., and Wigley, D. B. (1997) The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Proteins 28, 41-52.
22. Thuy, T. T. T., Lee, H. C., Kim, C., Heide, L., and Sohng, J. K. (2005) Functional characterization of novWUS involved in novobiocin biosynthesis from Streptomyces spheroides. Arch. Biochem. Biophys. 436, 161-167.
23. Couch, R., O'Connor, S., Seidle, H., Walsh, C. T., and Parry, R. (2004) Characterization of CmaA, an adenylation-thiolation di-domain enzyme involved in the biosynthesis of coronatine. J. Bacteriol. 186, 35-42.
24. 2-dependent halogenase. Proc. Natl. Acad. Sci. U.S.A. 102, 10111-10116.
25. Yeh, E., Garneau, S., and Walsh, C. T. (2005) Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 102, 3960-3965.