The albonoursin gene cluster of S. noursei: Biosynthesis of diketopiperazine metabolites independent of nonribosomal peptide synthetases

Chemistry and Biology

Volumn 9, Issue 12, 2002, Pages 1355-1364

  Lautru, Sylvie ^a,b,c   Gondry, Muriel ^a   Genet, Roger ^a   Pernodet, Jean Luc ^b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES LIVIDANS; STREPTOMYCES NOURSEI;

EID: 0036914164     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(02)00285-5     Document Type: Article

References (35)

1. Fischer E. Untersuchungen über Aminosäuren, Polypeptide und Proteine. 1906;Springer, Berlin.
2. Magyar A., Zhang X., Abdi F., Kohn H., Widger W. Identifying the bicyclomycin binding domain through biochemical analysis of antibiotic-resistant Rho proteins. J. Biol. Chem. 274:1999;7316-7324.
3. Waring P., Beaver J. Gliotoxin and related epipolythiodioxopiperazines. Gen. Pharmacol. 27:1996;1311-1316.
4. Chu M., Truumees I., Rothofsky M.L., Patel M.G., Gentile F., Das P.R., Puar M.S., Lin S.L. Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazines produced by Gliocladium sp. J. Antibiot. 48:1995;1440-1445.
5. Kanoh K., Kohno S., Katada J., Takahashi J., Uno I. Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization. J. Antibiot. 52:1999;134-141.
6. Williams D.E., Bombuwala K., Lobkovsky E., Dilip de Silva E., Karunaratne V., Allen T.M., Clardy J., Andersen R.J. Ambewelamides A and B, antineoplastic epidithiapiperazinediones isolated from the lichen Usnea sp. Tetrahedron Lett. 39:1998;9579-9582.
7. Walzel B., Riederer B., Keller U. Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea. Chem. Biol. 4:1997;223-230.
8. Schwarzer D., Mootz H.D., Marahiel M.A. Exploring the impact of different thioesterase domains for the design of hybrid peptide synthetases. Chem. Biol. 8:2001;997-1010.
9. Healy F.G., Wach M., Krasnoff S.B., Gibson D.M., Loria R. The txtAB genes of the plant pathogen Streptomyces acidiscabies encode a peptide synthetase required for phytotoxin thaxtomin A production and pathogenicity. Mol. Microbiol. 38:2000;794-804.
10. Rajappa S., Natekar M.V. Piperazine-2,5-diones and related lactim ethers. Adv. Heter. Chem. 57:1993;187-289.
11. Moss J., Bundgaard H. Kinetics and mechanism of the facile cyclization of histidyl-prolineamide to cyclo (His-Pro) in aqueous solution and the competitive influence of human plasma. J. Pharm. Pharmacol. 42:1990;7-12.
12. Gondry M., Lautru S., Fusai G., Meunier G., Ménez A., Genet R. Cyclic dipeptide oxidase from Streptomyces noursei. Isolation, purification and partial characterization of a novel, amino acyl alpha,beta-dehydrogenase. Eur. J. Biochem. 268:2001;1712-1721.
13. Kieser T., Bibb M.J., Buttner M.J., Chater K.F., Hopwood D.A. Practical Streptomyces Genetics. 2000;The John Innes Foundation, Norwich, UK.
14. 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.
15. 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.
16. Leskiw B.K., Bibb M.J., Chater K.F. The use of a rare codon specifically during development? Mol. Microbiol. 5:1991;2861-2867.
17. Krogh A., Larsson B., von Heijne G., Sonnhammer E.L.L. Predicting transmembrane protein topology with a hidden Markov model. Application to complete genomes J. Mol. Biol. 305:2001;567-580.
18. Kanzaki H., Imura D., Nitoda T., Kawazu K. Enzymatic dehydrogenation of cyclo(L-Phe-L-Leu) to a bioactive derivative, albonoursin. J. Mol. Catal. B: Enzymatic. 6:1999;265-270.
19. Khokhlov A.S., Lokshin G.B. The structure of albonoursin. Tetrahedron Lett. 27:1963;1881-1885.
20. Fukushima K., Yazawa K., Arai T. Biological activities of albonoursin. J. Antibiot. 26:1973;175-176.
21. Parkinson G.N., Skelly J.V., Neidle S. Crystal structure of FMN-dependent nitroreductase from Escherichia coli B. a prodrug-activating enzyme J. Med. Chem. 43:2000;3624-3631.
22. Tanner J.T., Lei B., Tu S.-C., Krause K.L. Flavin reductase P. structure of a dimeric enzyme that reduces flavin Biochemistry. 35:1996;13531-13539.
23. Kobori T., Sasaki H., Lee W.C., Zenno S., Saigo K. Structure and site-directed mutagenesis of a flavoprotein from Escherichia coli that reduces nitrocompounds. Alteration of pyridine nucleotide binding by a single amino acid substitution. J. Biol. Chem. 276:2001;2816-2823.
24. Hecht H.J., Erdmann H., Park H.J., Sprinzl M., Schmid R.D. Crystal structure of NADH oxidase from Thermus thermophilus. Nat. Struct. Biol. 2:1995;1109-1114.
25. Murzin A.G. Structural classification of proteins. new superfamilies Curr. Opin. Struct. Biol. 6:1996;386-394.
26. Keefe A.D., Szostak J.W. Functional proteins from a random-sequence library. Nature. 410:2001;715-718.
27. Holden M.T., Ram Chhabra S., de Nys R., Stead P., Bainton N.J., Hill P.J., Manefield M., Kumar N., Labatte M., England D.et al. Quorum-sensing cross talk. isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other gram-negative bacteria Mol. Microbiol. 33:1999;1254-1266.
28. Degrassi G., Aguilar C., Bosco M., Zahariev S., Pongor S., Venturi V. Plant growth-promoting Pseudomonas putida WCS358 produces and secretes four cyclic dipeptides. Cross-talk with quorum sensing bacterial sensors Curr. Microbiol. 45:2002;250-254.
29. Hopwood D.A., Kieser T., Wright H.M., Bibb M.J. Plasmids, recombination and chromosome mapping in Streptomyces lividans 66. J. Gen. Microbiol. 129:1983;2257-2269.
30. Gourmelen A., Blondelet-Rouault M.H., Pernodet J.L. Characterization of the glycosyltransferase inactivating macrolides, encoded by gimA from Streptomyces ambofaciens. Antimicrob. Agents Chemother. 42:1998;2612-2619.
31. Blondelet-Rouault M.H., Weiser J., Lebrihi A., Branny P., Pernodet J.L. Antibiotic resistance gene cassettes derived from the omega interposon for use in E. coli and Streptomyces. Gene. 190:1997;315-317.
32. Doumith M., Weingarten P., Wehmeier U.F., Salah-Bey K., Benhamou C., Capdevila C., Michel J.M., Piepersberg W., Raynal M.C. Analysis of genes involved in 6-deoxyhexose biosynthesis and transfer in Saccharopolyspora erythraea. Mol. Gen. Genet. 264:2000;477-485.
33. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning. A Laboratory Manual:1989;Cold Spring Harbor Laboratory Press, New York.
34. Altschul S.F., Madden T.L., Schaffer A.A., Zhang J., Zhang Z., Miller W., Lipman D.J. Gapped BLAST and PSI-BLAST. a new generation of protein database search programs Nucleic Acids Res. 25:1997;3389-3402.
35. Pearson W.R. Rapid and sensitive sequence comparison with FASTP and FASTA. Methods Enzymol. 183:1990;63-98.