Genes encoding synthetases of cyclic depsipeptides, anabaenopeptilides, in Anabaena strain 90

Molecular Microbiology

Volumn 37, Issue 1, 2000, Pages 156-167

  Rouhiainen, Leo ^a   Paulin, Lars ^a   Suomalainen, Sini ^a   Hyytiäinen, Heidi ^a   Buikema, William ^a   Haselkorn, Robert ^a   Sivonen, Kaarina ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANABAENOPEPTILIDE; BACTERIAL DNA; BACTERIAL PROTEIN; CHLORAMPHENICOL; CYANOGINOSIN; DEPSIPEPTIDE; HALOGEN; METHYLTRANSFERASE; OLIGONUCLEOTIDE; PEPTIDE DERIVATIVE; PEPTIDE SYNTHASE; SYNTHETASE; TRANSFERASE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANABAENA; ANTIBIOTIC RESISTANCE; BACTERIAL GENE; CYANOBACTERIUM; GENE AMPLIFICATION; GENE CLUSTER; GENE INSERTION; LIVER TOXICITY; MASS SPECTROMETRY; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN STRUCTURE; REVIEW;

AMINO ACID SEQUENCE; ANABAENA; GENES, BACTERIAL; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; MUTAGENESIS, INSERTIONAL; OPERON; PEPTIDE SYNTHASES; PEPTIDES, CYCLIC; POLYMERASE CHAIN REACTION; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, DNA; SUBSTRATE SPECIFICITY;

ANABAENA; ANABAENA SP. 90; BACTERIA (MICROORGANISMS); CYANOBACTERIA; PROKARYOTA;

EID: 0033926435     PISSN: 0950382X     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2958.2000.01982.x     Document Type: Review

References (53)

1. Altschul, S.F., Gish, W., Miller, W., Meyers, E.W., and Lipman, D.J. (1990) Basic local alignment search tool. J Mol Biol 215: 403-410.
2. Cosmina, P., Rodriguez, F., De Ferra, F., Grandi, G., Perego, M., Venema, G., et al. (1993) Sequence and analysis of the genetic locus responsible for surfactin synthesis in Bacillus subtilis. Mol Microbiol 8: 821-831.
3. Dairi, T., Nakano, T., Aisaka, K., Katsumata, R., and Hasegawa, M. (1995) Cloning and nucleotide sequence of the gene responsible for chlorination of tetracycline. Biosci Biotechnol Biochem 59: 1099-1106.
4. de Crècy-Lagard, V., Marlière, P., and Saurin, W. (1995) Multienzymatic non-ribosomal peptide biosynthesis: identification of the functional domains catalysing peptide elongation and epimerisation. C R Acad Sci Paris 318: 927-936.
5. Dittmann, E., Neilan, B.A., Erhard, M., von Döhren, H., and Börner, T. (1997) Insertional mutagenesis of a peptide synthetase gene that is responsible for hepatotoxin production in the cyanobacterium Microcystis aeruginosa PCC7806. Mol Microbiol 26: 779-787.
6. von Döhren, H., Keller, U., Vater, J., and Zocher, R. (1997) Multifunctional peptide synthetases. Chem Rev 97: 2675-2705.
7. Erhard, M., von Döhren, H., and Jungblut, P. (1997) Rapid typing and elucidation of new secondary metabolites of intact cyanobacteria using MALDI-TOF mass spectrometry. Nature Biotechnol 15: 906-909.
8. Fonstein, M., Zheng, S., and Haselkorn, R. (1992) Physical map of the genome of Rhodobacter capsulatus SB1003. J Bacteriol 174: 4070-4077.
9. Fujii, K., Harada, K.-I., Suzuki, M., Kondo, F., Ikai, Y., Oka, H., et al. (1996) Occurrence of novel cyclic peptides together with microcystins from toxic cyanobacteria, Anabaena species. In Harmful and Toxic Algal Blooms. Yasumoto, T., Oshima, Y., and Fukuyo, Y. (eds). Paris: Intergovermental Oceanographic Commission of UNESCO, pp. 559-562.
10. Genetics Computer Group (1994) Sequence Analysis Software Package, Version 8.0. Madison, WI: University of Wisconsin Genetics Computer Group.
11. Gibson, T.J., Rosenthal, A., and Waterston, R.H. (1987) Lorist 6, a cosmid vector with BamHI, NotI, ScaI and HindIII cloning sites and altered neomycin phosphotransferase gene expression. Gene 53: 283-286.
12. Gocht, M. and A., Marahiel, M. and A. (1994) Analysis of core sequences in the D-Phe activating domain of the multifunctional peptide synthetase TycA by site-directed mutagenesis. J Bacteriol 176: 2654-2662.
13. Golden, J.W., Carrasco, C.D., Mulligan, M.E., Scneider, G.J., and Haselkorn, R. (1988) Deletion of a 55-kilobasepair DNA element from the chromosome during heterocyst differentiation of Anabaena sp. strain PCC 7120. J Bacteriol 170: 5034-5041.
14. f formyltransferase severely impairs growth of Escherichia coli. J Bacteriol 174: 4294-4301.
15. Haese, A., Schubert, M., Herrmann, M., and Zocher, R. (1993) Molecular characterization of the enniatin synthetase gene encoding a multifunctional enzyme catalysing N-methyldepsipeptide formation in Fusarium scirpi. Mol Microbiol 7: 905-914.
16. Haese, A., Pieper, R., von Ostrowski, T., and Zocher, R. (1994) Bacterial expression of catalytically active fragments of the multifunctional enzyme enniatin synthetase. J Mol Biol 243: 116-122.
17. Hammer, P.E., Hill, D.S., Lam, ST., van Pee, K.-H., and Ligon, J.M. (1997) Four genes from Pseudomonas fluorescens that encode the biosynthesis of pyrrolnitrin. Appl Environ Microbiol 63: 2147-2154.
18. Ingrosso, D., Fowler, A.V., Bleibaum, J., and Clarke, S. (1989) Sequence of the D-aspartyl/L-iso-aspartyl protein methyltransferase from human erythrocytes. J Biol Chem 264: 20131-20139.
19. Kagan, R.M., and Clarke, S. (1994) Widespread occurrence of three sequence motifs in diverse S-adenosylmethionine-dependent methyltransferases suggests a common structure for these enzymes. Arch Biochem Biophys 310: 417-427.
20. Kaneko, T., Tanaka, A., Sato, S., Kotani, H., Sazuka, T., Miyajima, N., et al. (1995) Sequence analysis of the genome of the unicellular cyanobacterium Synechocystis sp. strain PCC 6803. I. Sequence features in the 1Mb region from map positions 64% to 92% of the genome. DNA Res 2: 153-166.
21. Kirner, S., Hammer, P.E., Hill, D.S., Altmann, A., Fischer, I., Weislo, L.J., et al. (1998) Functions encoded by pyrrolnitrin biosynthesis genes from Pseudomonas fluorescens. J Bacteriol 180: 1939-1943.
22. Kleinkauf, H., and von Döhren, H. (1996) A nonribosomal system of peptide biosynthesis. Eur J Biochem 236: 335-351.
23. Kotai, J. (1972) Instructions for Preparation of Modified Nutrient Solution Z8 for Algae. Publication B-11/69. Blindern, Oslo: Norwegian Institute for Water Research.
24. Krätzschmar, J., Krause, M., and Marahiel, M.A. (1989) Gramicidin S biosynthesis operon containing the structural genes grsA and grsB has an open reading frame encoding a protein homologous to fatty acid thioesterases. J Bacteriol 171: 5422-5429.
25. MacKintosh, C., Beattie, K.A., Klumpp, S., Cohen, P., and Codd, G.A. (1990) Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatase 1 and 2A from both mammals and higher plants. FEBS Lett 264: 187-192.
26. Marahiel, M.A., Stachelhaus, T., and Mootz, H.D. (1997) Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem Rev 97: 2651-2673.
27. Mazel, D., Coic, E., Blanchard, S., Saurin, W., and Marliere, P. (1997) A survey of polypeptide deformylase function throughout the eubacterial lineage. J Mol Biol 266: 939-949.
28. Naggert, J., Witkowski, A., Mikkelsen, J., and Smith, S. (1988) Molecular cloning and sequencing of a cDNA encoding the thioesterase domain of the rat fatty acid synthetase. J Biol Chem 263: 1146-1150.
29. Namikoshi, M., and Rinehart, K.L. (1996) Bioactive compounds produced by cyanobacteria. J Ind Microbiol 17: 373-384.
30. Neilan, B.A., Dittmann, E., Rouhiainen, L., Bass, R.A., Schaub, V., Sivonen, K., et al. (1999) Nonribosomal peptide synthesis and toxigenicity of cyanobacteria. J Bacteriol 181: 4089-4097.
31. Nishizawa, T., Asayama, M., Fuji, K., Harada, K.-I., and Shirai, M. (1999) Genetic analysis of the peptide synthetase genes for a cyclic heptapeptide microcystin in Microcystis spp. J Biochem 126: 520-529.
32. Nowak-Thompson, B., Chaney, N., Wing, J.S., Gould, S.J., and Loper, J.E. (1999) Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens PF-5. J Bacteriol 181: 2166-2174.
33. Pavela-Vrancic, M., Pfeifer, E., von Liempt, H., Schäfer, H.-J., von Döhren, H., and Kleinkauf, H. (1994) ATP binding in peptide synthetases: determination of contact sites of the adenine moiety by photoaffinity labeling of tyrocidine synthetase 1 with 2-azidoadenosine triphosphate. Biochemistry 33: 6276-6283.
34. Pieper, R., Haese, A., Schröder, W., and Zocher, R. (1995) Arrangement of catalytic sites in the multifunctional enzyme enniatin synthetase. Eur J Biochem 230:119-126.
35. Rouhiainen, L., Sivonen, K., Buikema, W., and Haselkorn, R. (1995) Characterization of toxin-producing cyanobacteria by using an oligonucleotide probe containing a tandemly repeated heptamer. J Bacteriol 177: 6021-6026.
36. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989) Molecular Cloning. A Laboratory Manual, 2nd edn. Plainview, NY: Cold Spring Harbor Laboratory Press.
37. Schlumbohm, W., Stein, T., Ullrich, C., Vater, J., Krause, M., Marahiel, M.A., et al. (1991) An active serine is involved in covalent substrate amino acid binding at each reaction center of gramicidin S synthetase. J Biol Chem 266: 23135-23141.
38. Schneider, A., and Marahiel, M.A. (1998) Genetic evidence for a role of thioesterase domains, integrated in or associated with peptide synthetases, in non-ribosomal peptide biosynthesis in Bacillus subtilis. Arch Microbiol 169: 404-410.
39. Scrutton, N.S., Berry, A., and Perham, R.N. (1990) Redesign of the coenzyme specificity of a dehydrogenase by protein engineering. Nature 343: 38-43.
40. Shaw-Reid, C.A., Kelleher, N.L., Losey, H.C., Gehring, A.M., Berg, C., and Walsh, C.T. (1999) Assembly line enzymology by multimodular nonribosomal peptide synthetases: the thioesterase domain of E. coli EntF catalyzes both elongation and cyclolactonization. Chem Biol 6: 385-400.
41. Sivonen, K., and Jones, G. (1999) Cyanobacterial toxins. In Toxic Cyanobacteria in Water: a Guide to their Public Health Consequences, Monitoring and Management. Chorus, I., and Bertram, J. (eds). London: E. & F.N. Spon, pp. 41-111.
42. Sivonen, K., Namikoshi, M., Evans, W.R., Carmichael, W.W., Sun, F., Rouhiainen, L., et al. (1992) Isolation and characterization of a variety of microcystins from seven strains of the cyanobacterial genus, Anabaena. Appl Environ Microbiol 58: 2495-2500.
43. Stachelhaus, T., and Marahiel, M.A. (1995a) Modular structure of genes encoding multifunctional peptide synthetases required for non-ribosomal peptide synthesis. FEMS Microbiol Lett 125: 3-14.
44. Stachelhaus, T., and Marahiel, M.A. (1995b) Modular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA. J Biol Chem 270: 6163-6169.
45. Stachelhaus, T., Mootz, H.D., Bergendahl, V., and Marahiel, M.A. (1998) Peptide bond formation in nonribosomal peptide biosynthesis: catalytic role of the condensation domain. J Biol Chem 273: 22773-22781.
46. Stachelhaus, T., Mootz, H.D., and Marahiel, M.A. (1999) The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem Biol 6: 493-505.
47. Stein, T., Vater, J., Kruft, V., Otto, A., Wittmann-Liebold, B., Franke, P., et al. (1996) The multiple carrier model of nonribosomal peptide biosynthesis at modular multienzymatic templates. J Biol Chem 271: 15428-15435.
48. Thompson, J.D., Higgins, D.G., and Gibson, T.J. (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighing, positions-specific gap penalties and weight matrix choice. Nucleic Acids Res 22: 4673-4680.
49. Turgay, K., Krause, M., and Marahiel, M.A. (1992) Four homologous domains in the primary structure of GrsB are related to domains in a superfamily of adenylate-forming enzymes. Mol Microbiol 6: 529-546.
50. Weber, G., Schörgendorfer, K., Schneider-Scherzer, E., and Leitner, E. (1994) The peptide synthetase catalyzing cyclosporine production in Tolypocladium niveum is encoded by a giant 45.8-kilobase open reading frame. Curr Genet 26: 120-125.
51. Weckesser, J., Martin, C., and Jakobi, C. (1996) Cyanopeptolins, depsipeptides from cyanobacteria. Syst Appl Microbiol 19: 133-138.
52. Yoshizawa, S., Matsushima, R., Watanabe, M.F., Harada, K-I., Ichihara, A., Carmichael, W.W., and Fujiki, K. (1990) Inhibition of protein phosphotases by microcystins and nodularins associated with hepatotoxicity. J Cancer Res Clin Oncol 116: 609-614.
53. Yuan, Z., Liu, W., and Hammes, G.G. (1988) Molecular cloning and sequencing of DNA complementary to chicken liver fatty acid synthetase mRNA. Proc Natl Acad Sci USA 85: 6328-6331.