Characterization of the enzymatic domains in the modular polyketide synthase involved in rifamycin B biosynthesis by Amycolatopsis mediterranei

Gene

Volumn 216, Issue 2, 1998, Pages 255-265

  Tang, Li ^a   Yoon, Yeo J ^a   Choi, Cha Yong ^b   Hutchinson, C Richard ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b Seoul National University   (South Korea)

Author keywords

Antibiotics; Modular PKS; Sequence homology

Indexed keywords

3 AMINO 5 HYDROXYBENZOIC ACID; ACYL CARRIER PROTEIN; BENZOIC ACID DERIVATIVE; MALONYL COENZYME A; POLYKETIDE SYNTHASE; RIFAMYCIN B; SYNTHETASE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANTIBIOTIC BIOSYNTHESIS; ARTICLE; CONSENSUS SEQUENCE; CONTROLLED STUDY; DEHYDRATION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GENE SEQUENCE; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN DOMAIN; SEQUENCE HOMOLOGY;

3-OXOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE; ACTINOBACTERIA; ACYL CARRIER PROTEIN; ACYLTRANSFERASES; AMINO ACID SEQUENCE; BINDING SITES; CLONING, MOLECULAR; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; MULTIENZYME COMPLEXES; PROTEIN STRUCTURE, TERTIARY; RIFAMYCINS; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY;

AMYCOLATOPSIS MEDITERRANEI; PROKARYOTA;

EID: 0032584941     PISSN: 03781119     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-1119(98)00338-2     Document Type: Article

References (30)

1. August P.R., Tang L., Yoon Y.J., Ning S., Müller R., Yu T.-W., Taylor M., Hoffmann D., Kim C.-G., Zhang X., Hutchinson C.R., Floss H.G. Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular anaysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699. Chem. Biol. 5:1998;69-79.
2. Aparicio J.F., Molnár I., Schwecke T., König A., Hydock S.F., Khaw L.E., Staunton J., Leadlay P.F. Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of the enzymatic domains in the modular polyketide synthase. Gene. 169:1996;9-16.
3. Beck J., Ripka S., Siegner A., Schiltz E., Schweiser E. The multifunctional 6-methylsalicylic acid synthase gene of Penicillium patulum. Its gene stucture relative to that of other polyketide synthases. Eur. J. Biochem. 192:1990;487-498.
4. Bevitt D.J., Cortés J., Haydock S.F., Leadlay P.F. 6-Deoxyerythronolide B synthase 2 from Saccharopolyspora erythraea. Cloning of the structural gene, sequence analysis and inferred domain structure of the mutifunctional enzyme. Eur. J. Biochem. 204:1992;39-49.
5. Connerton I.F., Fincham J.R., Sandeman R.A., Hynes M.J. Comparison and cross-species expression of the acetyl-CoA synthetase genes of the Ascomycete fungi Aspergillus nidulans and Neurospora crassa. Mol. Microbol. 4:1990;451-460.
6. Devereux J., Haeberli P., Smithies O. A comprehensive set of sequence analysis programs for the VAX. Nucl. Acids Res. 12:1984;387-395.
7. Dickinson J.M., Mitchison D.A. In vitro activity of new rifamycins against rifampicin-resistant M. tuberculosis and MAIS complex mycobacteria. Tubercule. 68:1987;177-182.
8. Donadio S., Katz L. Organization of the enzymatic domains in the multifuctional polyketide synthase involved in erythromycin formation in Saccharopolyspora erythraea. Gene. 111:1992;51-60.
9. Donadio S., Staver M.J., McAlpine J.B., Swanson S.J., Katz L. Modular organization of the genes required for complex polyketide biosynthesis. Science. 252:1991;675-679.
10. Grundy F.J., Waters D.A., Takova T.Y., Henkin T.M. Identification of genes involved in utilization of acetate and acetoin in Bacillus subtilis. Mol. Microbiol. 10:1993;259-271.
11. Haydock S., Aparicio J.F., Molnar I., Schwecke T., König A., Marsden A.F.A., Galloway I.S., Staunton J., Leadlay P.F. Divergent structural motifs correlated with the substrate specificity of (methyl)malonyl-CoA: acyl carrier protein transacylase domains in modular polyketide synthase. FEBS Lett. 374:1995;246-248.
12. Hu Z., Bao K., Zhou X., Zhou Q., Hopwood D.A., Kieser T., Deng Z. Repeated polyketide synthase modules involved in the biosynthesis of a heptaene macrolide by Streptomyces sp. FR-008. Mol. Microbiol. 14:1994;163-172.
13. Huang W., Jia J., Edwards J., Dehesh K., Schneider G., Lindqvist Y. Crystal structure of β-ketoacyl-acyl carrier protein synthase II from E. coli reveals the molecular architecture of condensing enzyme. EMBO J. 17:1998;1183-1191.
14. Katz L. Manipulation of modular polyketide synthases. Chem. Rev. 97:1997;2557-2575.
15. Leesong M., Handerson B.S., Gilling J.R., Schwab J.M., Smith J.L. Structure of a dehydratase-isomerase from the bacterial pathway for biosynthesis of unsaturated fatty acids: two catalytic activities in one active site. Structure. 4:1996;253-264.
16. Lowden P.A.S., Böhm G.A., Staunton J., Leadlay P.F. The nature of the starter unit for the rapamycin polyketide synthase. Angew. Chem. Int. Ed. Engl. 35:1996;2249-2251.
17. MacNeil D.J., Occi J.L., Gewain K.M., MacNeil T., Gibbons P.H., Ruby C.L., Danis S.J. Complex organization of the Streptomyces avermitilis genes encoding the avermectin polyketide synthase. Gene. 115:1992;119-125.
18. Mandell, G.L., Sande, M.A., 1980. Drugs used in the chemotherapy of tuberculosis and leprosy. In: Goodman, A.G., Goodman, L.S., Gulman, A. (Eds.), The Pharmocological Basis of Therapeutics, 6th ed. Macmillan, New York, pp. 1203-1206.
19. Schupp T., Toupet C., Cluzel B., Neff S., Hill S., Beck J.J., Ligon J.M. A Sorangium cellulosum (myxobacterium) gene cluster for the biosynthesis of the macrolide antibiotic soraphen A: cloning, characterization, and homology to polyketide synthase genes from actinomycetes. J. Bacteriol. 177:1995;3673-3679.
20. Schupp T., Toupet C., Engel N., Goff S. Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei. FEMS Microbiol. Lett. 159:1998;201-207.
21. Schwecke T., Aparicio J.F., Molnár I., König A., Khaw L.E., Hydock S.F., Olinyk M., Caffrey P., Cortés J., Lester J.B., Böhm G.A., Staunton J., Leadlay P.F. The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl. Acad. Sci. USA. 92:1995;7839-7843.
22. Scrutton N.S., Berry A., Perham R.N. Redesign of the coenzyme specificity of a dehydrogenase by protein engineering. Nature. 343:1990;38-43.
23. Sensi P., Margalith P., Timbal M.T. Rifomycin, a new antibiotic. Preliminary report. . Farmaco. ED. Sci. 14:1959;146-147.
24. Serre L., Verbee E.C., Dauter Z., Stuitje A.R., Derewenda Z.S. The Escherichia coli malonyl-CoA:acyl carrier protein transacylase at 1.5 Å resolution. J. Biol. Chem. 270:1995;12961-12964.
25. Swan D.G., Rodriguez A.M., Vilches C., Méndez C., Salas J.A. Characterization of a Streptomyces antibioticus gene encoding a type I polyketide synthase which has an unusual coding sequence. Mol. Gen. Genet. 242:1994;358-362.
26. Wakil S.J. Fatty acid synthase, a proficient multifunctional enzyme. Biochemistry. 28:1989;4523-4530.
27. Wehrli W. Rifampin: mechanisms of actions and resistance. Rev. Infect. Dis. 5:1983;S407-S411.
28. Wehrli W., Staehelin M. Actions of rifamycins. Bacteriol. Rev. 35:1971;290-309.
29. Witkowski A., Rangan V.S., Randhawa Z.I., Amy C.M., Smith S. Structural organization of the multifuctional animal fatty-acid synthase. Eur. J. Biochem. 198:1991;571-579.
30. Woodley C.L., Kilburn J.O. In vitro susceptibility of Mycobacterium avium complex and Mycobacterium tuberculosis strains to a spiropiperidyl rifamycin. Am. Rev. Respir. Dis. 126:1982;586.