Iteration as Programmed Event during Polyketide Assembly; Molecular Analysis of the Aureothin Biosynthesis Gene Cluster

Chemistry and Biology

Volumn 10, Issue 12, 2003, Pages 1225-1232

  He, Jing ^a   Hertweck, Christian ^a  

^a HANS KNÖLL INSTITUTE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES THIOLUTEUS;

EID: 0346968190     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2003.11.009     Document Type: Article

References (49)

1. O'Hagan D. The Polyketide Metabolites. 1991;Ellis Horwood, Chichester, UK.
2. Cortés J., Haydcock S.F., Roberts G.A., Bevitt D.J., Leadlay P.F. An unusually large multifunctional polypeptide in the erythromycin-producing polyketide synthase Saccharopolyspora erythraea. Nature. 348:1990;176-178.
3. Donadio S., Staver M.J., McAlpine J.B., Swanson S.J., Katz L. Modular organisation of genes required for complex polyketide biosynthesis. Science. 252:1991;675-679.
4. Schwecke T., Aparicio J.F., Molnar I., König A., Khaw L.E., Haydock S.F., Oliynyk M., Caffrey P., Cortes J., Lester J.B.et al. The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl. Acad. Sci. USA. 92:1995;7839-7843.
5. August P.R., Tang L., Yoon Y.J., Ning S., Müller R., Yu T.-W., Taylor M., Hoffman D., Kim C.-G., Zhang X.et al. Biosynthesis of the ansamycin antibiotic rifamycin. deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699 Chem. Biol. 5:1998;69-79.
6. Xue Y., Zhao L., Liu H.W., Sherman D.H. A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae. architecture of metaboic diversity Proc. Natl. Acad. Sci. USA. 95:1998;12111-12116.
7. Yu T.W., Shen Y., Doi-Katayama Y., Tang L., Park C., Moore B.S., Hutchinson C.R., Floss H.G. Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively. Proc. Natl. Acad. Sci. USA. 96:1999;9051-9056.
8. Staunton J., Weissman K.J. Polyketide biosynthesis. a millennium review Nat. Prod. Rep. 18:2001;380-416.
9. Maeda K. A crystalline toxic substance of Streptomyces thioluteus producing aureothricin. J. Antibiot. 4:1953;137-138.
10. Schwartz J.L., Tishler M., Arison B.H., Shafer H.M., Omura S. Identification of mycolutein and pulvomycin as aureothin and libilomycin respectively. J. Antibiot. 29:1976;236-241.
11. Kakinuma K., Hanson C.A., Rinehart K.L. Spectinabilin, a new nitro-containing metabolite isolated from Streptomyces spectabilis. Tetrahedron. 32:1976;217-222.
12. Yamazaki M., Maebayashi Y., Katoh H., Ohishi J.-I., Koyama Y. Application of 13C-NMR to the biosynthetic investigations. II Biosynthesis of aureothin and related nitro-containing metabolites of Streptomyces luteoreticuli. Chem. Pharm. Bull. 23:1975;569-574.
13. Criado L.M., Martin J.F., Gil J.A. The pab gene of Streptomyces griseus, encoding p-aminobenzoic acid synthase, is located between genes possibly involved in candicidin biosynthesis. Gene. 126:1993;135-139.
14. Bierman M., Logan R., O'Brien K., Seno E.T., Rao R.N., Schoner B.E. Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene. 116:1992;43-49.
15. Zhou X., Deng Z., Firmin J.L., Hopwood D.A., Kieser T. Site-specific degradation of Steptomyces lividans DNA during electrophoresis in buffers contaminated with ferrous iron. Nucleic Acids Res. 16:1988;4341-4352.
16. Bibb M.J., Findlay P.R., Johnson M.W. The relationship between base composition and codon usage in bacterial genes and its use for the simple and reliable identification of protein-coding sequences. Gene. 30:1984;157-166.
17. Horinouchi S., Kito M., Nishiyama M., Furuya K., Hong S.K., Miyake K., Beppu T. Primary structure of AfsR, a global regulatory protein for secondary metabolite formation in Streptomyces coelicolor A3(2). Gene. 95:1990;49-56.
18. Edman J.C., Goldstein A.L., Erbe J.G. Para-aminobenzoate synthase gene of Saccharomyces cerevisiae encodes a bifunctional enzyme. Yeast. 9:1993;669-675.
19. Brown M.P., Aidoo K.A., Vining L.C. A role for pabAB, a p-aminobenzoate synthase gene of Streptomyces venezuelae ISPS5230, in chloramphenicol biosynthesis. Microbiol. 142:1996;1345-1355.
20. Blanc V., Gil P., Bamas-Jacques N., Lorenzon S., Zagorec M. Identification and analysis of genes from Streptomycetes pristinaespiralis encoding enzymes involved in the biosynthesis of the 4-dimethylamino-L- phenylalanine precursor of pristinamycin I. Mol. Microbiol. 23:1997;191-202.
21. Green J.M., Nichols B.P. p-Aminobenzoate biosynthesis in Escherichia coli. Purification of aminodeoxychorismate lyase and cloning of pabC. J. Biol. Chem. 266:1991;12972-12975.
22. Campelo A.B., Gil J.A. The candicidin gene cluster from Streptomyces griseus IMRU 3570. Microbiol. 148:2002;51-59.
23. Hu Z.H., Boa K., Zhou X.F., Zhou Q., Hopwood D.A., Kieser T., Deng Z.H. Repeated polyketide synthase modules involved in the biosynthesis of a heptaene macrolide by Streptomyces sp. FR-. 008.(Mol. Microbiol. 14):1994;163-172.
24. Moore B.S., Hertweck C. Biosynthesis and attachment of novel bacterial polyketide synthase starter units. Nat. Prod. Rep. 19:2002;70-99.
25. Piel J., Hertweck C., Shipley P., Hunt D.S., Newman M.S., Moore B.S. Cloning, sequencing, and analysis of the enterocin biosynthesis gene cluster from the marine isolate "Streptomyces maritimus" evidence for the derailment of an aromatic polyketide synthase Chem. Biol. 7:2000;943-955.
26. Xiang L., Kalaitzis J.A., Nilsen G., Chen L., Moore B.S. Mutational analysis of the enterocin Favorskii biosynthetic rearrangement. Org. Lett. 4:2002;957-960.
27. 2115. J. Bacteriol. 181:1999;3419-3426.
28. Weber J.M., Leung J.O., Swanson S.J., Idler K.B., McAlpine J.B. An erythromycin derivative produced by targeted gene disruption in Saccharopolyspora erythraea. Science. 252:1991;114-117.
29. Ikeda H., Nonomiya T., Usami M., Ohta T., Omura S. Organization of the biosynthetic gene cluster for the polyketide anthelminthic macrolide avermectin in Streptomyces avermitilis. Proc. Natl. Acad. Sci. USA. 96:1999;9509-9514.
30. Haydock S.F., Aparicio J.F., Molnar I., Schwecke T., Khaw L.E., König A., Marsden A.F.A., Galloway I.S., Staunton J., Leadlay P.F. Divergent sequence motifs correlated with substrate specificity of (methyl)malonyl-CoA:acyl carrier protein transacylase domains in modular polyketide synthases. FEBS Lett. 374:1995;246-248.
31. Aparicio J.F., Molnar I., Schwecke T., König A., Haydcock S.F., Khaw L.E., Staunton J., Leadlay P.F. Organisation 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.
32. Nowak-Thompson B., Gould S.J., Loper J.E. Identification and sequence analysis of genes encoding a polyketide synthase required for pyoluteorin biosynthesis in Pseudomonas fluorescens Pf-5. Gene. 204:1997;17-24.
33. Cane D.E., Walsh C.T. The parallel and convergent universes of polyketide synthases and nonribosomal peptide synthetases. Chem. Biol. 6:1999;R319-R325.
34. Walsh C.T. Combinatorial biosynthesis of antibiotics. challenges and opportunities Chembiochem. 3:2002;124-134.
35. Kirner S., van Pee K.-H. The biosynthesis of nitro compounds. the enzymatic oxidation to pyrrolnitrin of its amino-substituted precursor Angew. Chem. Int. Ed. Engl. 33:1994;352-354.
36. Kirner S., Hammer P.E., Hill D.S., Altmann A., Fischer I., Weislo L.J., Lanahan M., van Pee K.-H., Ligon J.M. Functions encoded by pyrrolnitrin biosynthetic genes from Pseudomonas fluorescens. J. Bacteriol. 180:1998;1939-1943.
37. He J., Magarvey N., Piraee M., Vining L.C. The gene cluster for chloramphenicol biosynthesis in Streptomyces venezuelae ISPS5230 includes novel shikimate pathway homologues and a monomodular non-ribosomal peptide synthetase gene. Microbiol. 147:2001;2817-2829.
38. Aparicio J.F., Fouces R., Mendes M.V., Olivera N., Martin J.F. A complex multienzyme system encoded by five polyketide synthase genes is involved in the biosynthesis of the 26-membered polyene macrolide pimaricin in Streptomyces natalensis. Chem. Biol. 7:2000;895-905.
39. Hardt I.H., Steinmetz H., Gerth K., Sasse F., Reichenbach H., Höfle G. New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13. isolation, structure elucidation and SAR studies J. Nat. Prod. 64:2001;847-856.
40. Wilkinson B., Foster G., Rudd B.A.M., Taylor N.L., Blackaby A.P., Sidebottom P.J., Cooper D.J., Dawson M.J., Buss A.D., Gaisser S.et al. Novel octaketide macrolides related to 6-deoxyerythronolide B provide evidence for iterative operation of the erythromycin polyketide synthase. Chem. Biol. 7:2000;111-117.
41. Staunton J., Caffrey P., Aparicio J.F., Roberts G.A., Bethell S.S., Leadlay P.F. Evidence for a double-helical structure for modular polyketide synthases. Nat. Struct. Biol. 3:1996;188-192.
42. Gokhale R.S., Lau J., Cane D.E., Khosla C. Functional orientation of the acyltransferase domain in a module of the erythromycin polyketide synthase. Biochemistry. 37:1998;2524-2528.
43. Gaitatzis N., Silakowski B., Kunze B., Nordsiek G., Blöker H., Höfle G., Müller R. The biosynthesis of the aromatic myxobacterial electron transport inhibitor stigmatellin is directed by a novel type of modular polyketide synthase. J. Biol. Chem. 277:2002;13082-13090.
44. Beck B.J., Aldrich C.C., Fecik R.A., Reynolds K.A., Sherman D.H. Iterative chain elongation by a pikromycin monomodular polyketide synthase. J. Am. Chem. Soc. 125:2003;4682-4683.
45. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., Hopwood D.A. Practical Streptomyces Genetics. 2000;The John Innes Foundation, Norwich, UK.
46. Li A., Piel J. A gene cluster from a marine Streptomyces encoding the biosynthesis of the spiroketal polyketide griseorhodin A. Chem. Biol. 9:2002;1017-1026.
47. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning. A Laboratory Manual Second Edition:1989;Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
48. Alting-Mees M.A., Short J.M. pBluescript II. gene mapping vectors Nucleic Acids Res. 17:1989;9494.
49. Brautaset T., Sekurova O.N., Sletta H., Ellingsen T.E., Strom A.R., Valla S., Zotchev S.B. Biosynthesis of the polyene antifungal antibiotic nystatin in Streptomyces noursei ATCC 11455. analysis of the gene cluster and deduction of the biosynthetic pathway Chem. Biol. 7:2000;395-403.