5S Clavam Biosynthetic Genes Are Located in Both the Clavam and Paralog Gene Clusters in Streptomyces clavuligerus

Chemistry and Biology

Volumn 14, Issue 2, 2007, Pages 131-142

  Tahlan, Kapil ^a   Anders, Cecilia ^a   Wong, Annie ^a   Mosher, Roy H ^a   Beatty, Perrin H ^a   Brumlik, Michael J ^a   Griffin, Allison ^b   Hughes, Claire ^b   Griffin, John ^b   Barton, Barry ^b   Jensen, Susan E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

CHEMBIOL; MICROBIOL

Indexed keywords

BACTERIAL DNA; CLAVAM; CLAVULANIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; DNA SEQUENCE; GENE EXPRESSION REGULATION; GENETICS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MULTIGENE FAMILY; SOUTHERN BLOTTING; STREPTOMYCES;

BLOTTING, SOUTHERN; CHROMATOGRAPHY, LIQUID; CLAVULANIC ACID; CLAVULANIC ACIDS; DNA, BACTERIAL; GENES, BACTERIAL; MASS SPECTROMETRY; MULTIGENE FAMILY; MUTAGENESIS, INSERTIONAL; SEQUENCE ANALYSIS, DNA; STREPTOMYCES;

STREPTOMYCES CLAVULIGERUS;

EID: 33847161732     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2006.11.012     Document Type: Article

References (48)

1. Jensen S.E., and Paradkar A.S. Biosynthesis and molecular genetics of clavulanic acid. Antonie Van Leeuwenhoek 75 (1999) 125-133
2. Brown D., Evans J.R., and Fletton R.A. Structures of three novel β-lactams isolated from Streptomyces clavuligerus. J. Chem. Soc. Chem. Commun. 1979 (1979) 282-283
3. Higgens C.E., and Kastnar R.E. Streptomyces clavuligerus sp. nov. a β-lactam antibiotic producer. Int. J. Syst. Bacteriol. 21 (1971) 326-331
4. Baggaley K.H., Brown A.G., and Schofield C.J. Chemistry and biosynthesis of clavulanic acid and other clavams. Nat. Prod. Rep. 14 (1997) 309-333
5. Egan L.A., Busby R.W., Iwata-Reuyl D., and Townsend C.A. Probable role of clavaminic acid as the terminal intermediate in the common pathway to clavulanic acid and the antipodal clavam metabolites. J. Am. Chem. Soc. 119 (1997) 2348-2355
6. Nicholson N.H., Baggaley K.H., Cassels R., Davison M., Elson S.W., Fulston M., Tyler J.W., and Woroniecki S.R. Evidence that the immediate biosynthetic precursor of clavulanic acid is its N-aldehyde analog. J. Chem. Soc. Chem. Commun. 1994 (1994) 1281-1282
7. Arulanantham H., Kershaw N.J., Hewitson K.S., Hughes C.E., Thirkettle J.E., and Schofield C.J. ORF17 from the clavulanic acid biosynthesis gene cluster catalyses the ATP dependent formation of N-glycyl-clavaminic acid. J. Biol. Chem. 281 (2005) 279-287
8. Pruess D.L., and Kellett M. Ro 22-5417, a new clavam antibiotic from Streptomyces clavuligerus: I. Discovery and biological activity. J. Antibiot. (Tokyo) 36 (1983) 208-212
9. Tahlan K., Park H.-U., and Jensen S.E. Three unlinked gene clusters are involved in clavam metabolite biosynthesis in Streptomyces clavuligerus. Can. J. Microbiol. 50 (2004) 803-810
10. Ward J.M., and Hodgson J.E. The biosynthetic genes for clavulanic acid and cephamycin production occur as a 'super-cluster' in three Streptomyces. FEMS Microbiol. Lett. 110 (1993) 239-242
11. Jensen S.E., Elder K.J., Aidoo K.A., and Paradkar A.S. Enzymes catalyzing the early steps of clavulanic acid biosynthesis are encoded by two sets of paralogous genes in Streptomyces clavuligerus. Antimicrob. Agents Chemother. 44 (2000) 720-726
12. Jensen S.E., Paradkar A.S., Mosher R.H., Anders C., Beatty P.H., Brumlik M., Griffin A., and Barton B. Five additional genes are involved in clavulanic acid biosynthesis in Streptomyces clavuligerus. Antimicrob. Agents Chemother. 48 (2004) 192-202
13. Li R., Khaleeli N., and Townsend C.A. Expansion of the clavulanic acid gene cluster: identification and in vivo functional analysis of three new genes required for biosynthesis of clavulanic acid by Streptomyces clavuligerus. J. Bacteriol. 182 (2000) 4087-4095
14. Mellado E., Lorenzana L.M., Rodriguez-Saiz M., Diez B., Liras P., and Barredo J.L. The clavulanic acid biosynthetic cluster of Streptomyces clavuligerus: genetic organization of the region upstream of the car gene. Microbiology 148 (2002) 1427-1438
15. Perez-Redondo R., Rodriguez-Garcia A., Martin J.F., and Liras P. Deletion of the pyc gene blocks clavulanic acid biosynthesis except in glycerol-containing medium: evidence for two different genes in formation of the C3 unit. J. Bacteriol. 181 (1999) 6922-6928
16. Jensen S.E., Wong A., Griffin A., and Barton B. Streptomyces clavuligerus has a second copy of the proclavaminate amidinohydrolase gene. Antimicrob. Agents Chemother. 48 (2004) 514-520
17. Marsh E.N., Chang M.D., and Townsend C.A. Two isozymes of clavaminate synthase central to clavulanic acid formation: cloning and sequencing of both genes from Streptomyces clavuligerus. Biochemistry 31 (1992) 12648-12657
18. Tahlan K., Park H.-U., Wong A., Beatty P.H., and Jensen S.E. Two sets of paralogous genes encode the enzymes involved in the early stages of clavulanic acid and clavam metabolite biosynthesis in Streptomyces clavuligerus. Antimicrob. Agents Chemother. 48 (2004) 930-939
19. Mosher R.H., Paradkar A.S., Anders C., Barton B., and Jensen S.E. Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus. Antimicrob. Agents Chemother. 43 (1999) 1215-1224
20. Parry R.J., and Li W. An NADPH:FAD oxidoreductase from the valanimycin producer, Streptomyces viridifaciens. J. Biol. Chem. 272 (1997) 23303-23311
21. A synthase and NADH:riboflavin 5′-phosphate oxidoreductase. J. Bacteriol. 177 (1995) 5206-5214
22. Cunin R., Glansdorff N., Pierard A., and Stalon V. Biosynthesis and metabolism of arginine in bacteria. Microbiol. Rev. 50 (1986) 314-352
23. Antón N., Mendes M.V., Martín J.F., and Aparicio J.F. Identification of PimR as a positive regulator of pimaricin biosynthesis in Streptomyces natalensis. J. Bacteriol. 186 (2004) 2567-2575
24. Rigali S., Derouaux A., Giannotta F., and Dusart J. Subdivision of the helix-turn-helix GntR family of bacterial regulators in the FadR, HutC, MocR, and YtrA subfamilies. J. Biol. Chem. 277 (2002) 12507-12515
25. Eggeling L., and Sahm H. New ubiquitous translocators: amino acid export by Corynebacterium glutamicum and Escherichia coli. Arch. Microbiol. 180 (2003) 155-160
26. Rus'd A.A., Ikejiri Y., Ono H., Yonekawa T., Shiraiwa M., Kawada A., and Takahara H. Molecular cloning of cDNAs of mouse peptidylarginine deiminase type I, type III and type IV, and the expression pattern of type I in mouse. Eur. J. Biochem. 259 (1999) 660-669
27. Ichinose K., Bedford D.J., Tornus D., Bechthold A., Bibb M.J., Revill W.P., Floss H.G., and Hopwood D.A. The granaticin biosynthetic gene cluster of Streptomyces violaceoruber Tu22: sequence analysis and expression in a heterologous host. Chem. Biol. 5 (1998) 647-659
28. Gust B., Challis G.L., Fowler K., Kieser T., and Chater K.F. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 1541-1546
29. Talalay P., and Wang V.S. Enzymic isomerization of delta5-3-ketosteroids. Biochim. Biophys. Acta 18 (1955) 300-301
30. Ha N.-C., Choi G., Choi K.Y., and Oh B.-H. Structure and enzymology of delta5-3-ketosteroid isomerase. Curr. Opin. Struct. Biol. 11 (2001) 674-678
31. Nagai S., and Flavin M. Acetylhomoserine: an intermediate in the fungal biosynthesis of methionine. J. Biol. Chem. 242 (1967) 3884-3895
32. Gutiérrez S., Velasco J., Fernandez F.J., and Martín J.F. The cefG gene of Cephalosporium acremonium is linked to the cefEF gene and encodes a deacetylcephalosporin C acetyltransferase closely related to homoserine O-acetyltransferase. J. Bacteriol. 174 (1992) 3056-3064
33. Bentley S.D., Chater K.F., Cerdeno-Tarraga A.M., Challis G.L., Thomson N.R., James K.D., Harris D.E., Quail M.A., Kieser H., Harper D., et al. Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417 (2002) 141-147
34. Omura S., Ikeda H., Ishikawa J., Hanamoto A., Takahashi C., Shinose M., Takahashi Y., Horikawa H., Nakazawa H., Osonoe T., et al. Genome sequence of an industrial microorganism Streptomyces avermitilis: deducing the ability of producing secondary metabolites. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 12215-12220
35. Reiter W.D., Palm P., and Yeats S. Transfer RNA genes frequently serve as integration sites for prokaryotic genetic elements. Nucleic Acids Res. 17 (1989) 1907-1914
36. Shen B.W., Hennig M., Erhard Hohenester E., Jansonius J.N., and Tilman Schirmer T. Crystal structure of human recombinant ornithine aminotransferase. J. Mol. Biol. 277 (1998) 81-102
37. Rodríguez-García A., de La Fuente A., Pérez-Redondo R., Martín J.F., and Liras P. Characterization and expression of the arginine biosynthesis gene cluster of Streptomyces clavuligerus. J. Mol. Microbiol. Biotechnol. 2 (2000) 543-550
38. Kershaw N.J., McNaughton H.J., Hewitson K.S., Hernandez H., Griffin J., Hughes C., Greaves P., Barton B., Robinson C.V., and Schofield C.J. ORF6 from the clavulanic acid gene cluster of Streptomyces clavuligerus has ornithine acetyltransferase activity. Eur. J. Biochem. 269 (2002) 2052-2059
39. de la Fuente A., Martín J.F., Rodríguez-García A., and Liras P. Two proteins with ornithine acetyltransferase activity show different functions in Streptomyces clavuligerus: Oat2 modulates clavulanic acid biosynthesis in response to arginine. J. Bacteriol. 186 (2004) 6501-6507
40. Paradkar A.S., Aidoo K.A., and Jensen S.E. A pathway-specific transcriptional activator regulates late steps of clavulanic acid biosynthesis in Streptomyces clavuligerus. Mol. Microbiol. 27 (1998) 831-843
41. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., and Hopwood D.A. Practical Streptomyces Genetics (2000), John Innes Foundation, Norwich, England
42. Stuttard C. Temperate phages of Streptomyces venezuelae: lysogeny and host specificity shown by phages SV1 and SV2. J. Gen. Microbiol. 128 (1982) 115-121
43. Baltz R.H. Genetic recombination by protoplast fusion in Streptomyces. Dev. Indust. Micro. 21 (1980) 43-54
44. Sambrook J., Fritsch E.F., and Maniatis T. Molecular Cloning: A Laboratory Manual. Second Edition (1989), Cold Spring Harbour Laboratory Press, Cold Spring Harbour, NY
45. Bailey C.R., and Winstanley D.J. Inhibition of restriction in Streptomyces clavuligerus by heat treatment. J. Gen. Microbiol. 132 (1985) 2945-2947
46. Denis F., and Brzezinski R. An improved aminoglycoside resistance gene cassette for use in gram-negative bacteria and Streptomyces. FEMS Microbiol. Lett. 81 (1991) 261-264
47. Wehmeier U.F. New multifunctional Escherichia coli-Streptomyces shuttle vectors allowing blue-white screening on XGal plates. Gene 165 (1995) 149-150
48. Paradkar A.S., and Jensen S.E. Functional analysis of the gene encoding the clavaminate synthase 2 isoenzyme involved in clavulanic acid biosynthesis in Streptomyces clavuligerus. J. Bacteriol. 177 (1995) 1307-1314