Genetic architecture of the polyketide synthases for methymycin and pikromycin series macrolides

Gene

Volumn 245, Issue 1, 2000, Pages 203-211

  Xue, Yongquan ^a   Wilson, Daniel ^a   Sherman, David H ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Antibiotics; Gene cluster; Ketolide; Modular PKS

Indexed keywords

ERYTHROMYCIN; MACROLIDE; METHYMYCIN; OLEANDOMYCIN; PIKROMYCIN; SYNTHETASE;

ARTICLE; DRUG MANUFACTURE; GENE CLUSTER; GENE SEQUENCE; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STREPTOMYCES VENEZUELAE;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; BASE SEQUENCE; DNA, BACTERIAL; FATTY ACID SYNTHETASE COMPLEX; GENES, BACTERIAL; MACROLIDES; MOLECULAR SEQUENCE DATA; MULTIENZYME COMPLEXES; MULTIGENE FAMILY; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, NUCLEIC ACID; STREPTOMYCES; THIOLESTER HYDROLASES;

PROKARYOTA; STREPTOMYCES VENEZUELAE;

EID: 0034615668     PISSN: 03781119     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-1119(00)00003-2     Document Type: Article

References (31)

1. Agouridas C., Denis A., Auger J.M., Benedetti Y., Bonnefoy A., Bretin F., Chantot J.F., Dussarat A., Fromentin C., D'Ambrieres S.G., Lachaud S., Laurin P., Le Martret O., Loyau V., Tessot N. Synthesis and antibacterial activity of ketolides (6-O-methyl-3-oxoerythromycin derivatives) a new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens. J. Med. Chem. 41:1998;4080-4100.
2. 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.
3. Bisang C., Long P.F., Cortes J., Westcott J., Crosby J., Matharu A.L., Cox R.J., Simpson T.J., Staunton J., Leadlay P.F. A chain initiation factor common to both modular and aromatic polyketide synthesis. Nature. 401:1999;502-505.
4. Brockmann H., Hekel W. Pikromycin, ein bitter schmeckendes antibioticum aus actinomyeten. Chem. Ber. 84:1951;284-288.
5. Butler A.R., Bate N., Cundliffe E. Impact of thioesterase activity on tylosin biosynthesis in Streptomyces fradiae. Chem. Biol. 6:1999;287-292.
6. Cane D.E., Lambalot R.H., Prabhakaran P.C., Ott W.R. Macrolide biosynthesis 7. Incorporation of polyketide chain elongation intermediates into methymycin. J. Am. Chem. Soc. 115:1993;522-526.
7. Corbaz R., Ettlinger L., Gäumann E., Keller W., Kradofer F., Kyburz E., Neipp L., Prelog V., Reusser R., Zahner H. Stoffwechselprodukte von actinomyceten. Narbomycin. Helv. Chim. Acta. 38:1955;935-942.
8. Donadio S., Staver M.J., McAlpine J.B., Swanson S.J., Katz L. Modular organization of genes required for complex polyketide biosynthesis. Science. 252:1991;675-679.
9. Donin M.N., Pagano J., Dutcher J.D., McKee C.M. Methymycin a new crystalline antibiotic. Antobiot. Annu. 1:(54):1954;179-185.
10. Gokhale R.S., Tsuji S.Y., Cane D.E., Khosla C. Dissecting and exploiting intermodular communication in polyketide synthases. Science. 284:1999;482-485.
11. Haydock S.F., Aparicio J.F., Molnar I., Schwecke T., Khaw L.E., Konig A., Marsden A.F., Galloway I.S., Staunton J., Leadlay P.F. Divergent sequence motifs correlated with the substrate specificity of (methyl)malonyl-CoA:acyl carrier protein transacylase domains in modular polyketide synthases. FEBS Lett. 374:1995;246-248.
12. Hopwood D.A., Bibb M.J., Chater K.J., Kieser T., Bruton C.J., Kieser H.M., Lydiate D.J., Smith C.P., Ward J.M., Schrempf H. Genetic Manipulation of Streptomyces: A Laboratory Manual. 1985;The John Innes Foundation.
13. Hopwood D.A., Sherman D.H. Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Ann. Rev. Genet. 24:1990;37-66.
14. Hori T., Maezawa I., Nagahama N., Suzuki M. Isolation and structure of narbonolide, narbomycin aglycone from Streptomyces venezuelae and its biological transformation into picromycin via narbomycin. J. Am. Chem. Soc. Chem. Commun. 1971;304-305.
15. Kakavas S.J., Katz L., Stassi D. Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis. J. Bacteriol. 179:1997;7515-7522.
16. Kuhstoss S., Huber M., Turner J.R., Paschal J.W., Rao R.N. Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene. 183:1996;231-236.
17. Lambalot R.H., Cane D.E. Isolation and characterization of 10-deoxymethynolide produced by Streptomyces venezuelae. J. Antibiot. 45:1992;1981-1982.
18. McDaniel R., Kao C.M., Hwang S.J., Khosla C. Engineered intermodular and intramodular polyketide synthase fusions. Chem. Biol. 4:1997;667-674.
19. Maezawa I., Hori T., Kinumaki A., Suzuki M. Biological conversion of narbonolide to picromycin. J. Antibiot. 26:1973;771-775.
20. Marahiel M.A., Stachelhaus T., Mootz H.D. Modular peptide synthetases involved in nonribosomal peptide synthase synthesis. Chem. Rev. 97:1997;2651-2673.
21. Mikkelsen J., Witkowski A., Smith S. Interaction of rat mammary gland thioesterase II with fatty acid synthetase is dependent on the presence of acyl chains on the synthetase. J. Biol. Chem. 262:1987;1570-1574.
22. Mootz H.D., Marahiel M.A. The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains. J. Bacteriol. 179:1997;6843-6850.
23. 13C enriched precursors. J. Antibiot. 29:1976;316-317.
24. Perlman D., O'Brien E. Microbiological production of methymycin and related antibiotics. Antibiot. Chemother. 4:1953-1954;894-898.
25. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning: A Laboratory Manual. 1989;Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
26. Sherman D.H., Malpartida F., Bibb M.J., Kieser H.M., Hallam S.E., Robinson J.A., Bergh S., Ehlen M., Simpson T.J., Hopwood D.A. Cloning and Analysis of Genes for the Biosynthesis of Polyketide Antibiotics in Streptomyces Species. Proc. 8th Int. Symp. Biotechnol. Vol. 1:1988;123-137 Société Française de Microbiologie, Paris.
27. Swan D.G., Rodriguez A.M., Vilches C., Mendez C., Salas J.A. Characterisation of a Streptomyces antibioticus gene encoding a type I polyketide synthase which has an unusual coding sequence. Mol. Gen. Genet. 242:1994;358-362.
28. Tang L., Fu H., Betlach M.C., McDaniel R. Elucidating the mechanism of chain termination switching in the picromycin/methymycin polyketide synthase. Chem. Biol. 6:1999;553-558.
29. Xue Y., Sherman D.H. Alternative modular polyketide synthase expression controls macrolactone structure. Nature. 403:2000;571-575.
30. Xue Y., Wilson D., Zhao L., Liu H.w., Sherman D.H. Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem. Biol. 5:1998;661-667.
31. Xue Y., Zhao L., Liu H.W., Sherman D.H. A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc. Natl. Acad. Sci. USA. 95:1998;12 111-12 116.