Highly diverse cyanobactins in strains of the genus anabaena

Applied and Environmental Microbiology

Volumn 76, Issue 3, 2010, Pages 701-709

  Leikoski, Niina ^a   Fewer, David P ^a   Jokela, Jouni ^a   Wahlsten, Matti ^a   Rouhiainen, Leo ^a   Sivonen, Kaarina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ANABAENA SP; ANTI-TUMORS; CYCLIC PEPTIDES; CYTOTOXIC; GENE CLUSTERS; GENOME PROJECTS; HETEROLOGOUS EXPRESSION; POST-TRANSLATIONAL MODIFICATIONS; PRECURSOR PROTEINS; PROTEINOGENIC; PROTEOLYTIC CLEAVAGE; SEQUENCE VARIATIONS; STABLE-ISOTOPE LABELING; STRUCTURAL DIVERSITY;

AMINO ACIDS; BIOINFORMATICS; ESCHERICHIA COLI; GENE EXPRESSION; ISOTOPES; MASS SPECTROMETRY; ORGANIC ACIDS;

PEPTIDES;

AMINO ACID; BACTERIAL DNA; BACTERIAL PROTEIN; CYCLOPEPTIDE; MEMBRANE PROTEIN; RNA 16S;

AMINO ACID; BIOINFORMATICS; CYANOBACTERIUM; GENE; GENOME; MASS SPECTROMETRY; PEPTIDE; STABLE ISOTOPE;

AMINO ACID SEQUENCE; ANABAENA; ARTICLE; BACTERIAL GENE; CHEMISTRY; DNA SEQUENCE; ESCHERICHIA COLI; GENETIC ENGINEERING; GENETICS; MASS SPECTROMETRY; METABOLISM; MOLECULAR CLONING; MOLECULAR EVOLUTION; MOLECULAR GENETICS; MULTIGENE FAMILY; NUCLEOTIDE SEQUENCE; PHYLOGENY; SEQUENCE HOMOLOGY; TRANSPOSON;

AMINO ACID SEQUENCE; AMINO ACIDS; ANABAENA; BACTERIAL PROTEINS; CLONING, MOLECULAR; DNA TRANSPOSABLE ELEMENTS; DNA, BACTERIAL; ESCHERICHIA COLI; EVOLUTION, MOLECULAR; GENES, BACTERIAL; GENETIC ENGINEERING; MASS SPECTROMETRY; MEMBRANE PROTEINS; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; PEPTIDES, CYCLIC; PHYLOGENY; RNA, RIBOSOMAL, 16S; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, AMINO ACID;

ANABAENA; ANABAENA CIRCINALIS 90; CYANOBACTERIA; ESCHERICHIA COLI;

EID: 75749087607     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.01061-09     Document Type: Article

References (28)

1. Baba, T., and O. Schneewind. 1.998. Instruments of microbial warfare: bacteriocin synthesis, toxicity and immunity. Trends Microbiol. 6:66-71.
2. Baumann, H. I, S. Keller, F. E. Wolter, G. J. Nicholson, G. Jung, R. D. Susmuth, and F. Jüttner. 2007. Planktocyclin, a cyclooctapeptide protease inhibitor produced by the freshwater cyanobacterium Planktothrix rubescens. J. Nat. Prod. 70:1611-1615.
3. Donia, M. S., B. J. Hathaway, S. Sudek, M. G. Haygood, M. J. Rosovitz, J. Ravel, and E. W. Schmidt. 2006. Natural combinatorial peptide libraries in cyanobacterial symbionts of marine ascidians. Nat. Chem.. Biol. 2:729-735.
4. Donia, M. S., J. Ravel, and E. W. Schmidt. 2008. A global assembly line for cyanobactins, Nat. Chem. Biol. 4:341-343.
5. Donia, M. S., B. Wang, D. C. Dunbar, P. V. Desai, A. Patny, M. Avery, and M. T. Hamann. 2008. Mollamides B and C, cyclic hexapeptides from the Indonesian tunicate Didemnum molle. J. Nat. Prod. 71:941-945.
6. Erickson, K. L., K. R. Gustafson, D. J. Milanowski, L. K. Pannell, J. R. Klose, and M. R. Boyd. 2003. Myriastramides A-C, new modified cyclic peptides from the Philippines marine sponge Myriastra clavosa. Tetrahedron 59:10231-10238.
7. Fujii, K., K. Sivonen, E. Naganawa, and K.-I. Harada. 2000. Non-toxic peptides from toxic cyanobacteria, Oscillatoria agardhii. Tetrahedron 56: 725-733.
8. Garo, E., J.-L. Wolfender, K. Hostettmann, W. Hiller, S. Antus, and S. Mavi. 1998. Prenylated flavanones from Monotes engleri: on-line structure elucidation, by LC/UV/NMR. HeIv. Chim. Acta 81:754-763.
9. Gesner-Apter, S., and S. Carmeli. 2008. Three novel metabolites from, bloom of the cyanobacterium Microcystis sp. Tetrahedron 64:6628-6634.
10. Ishida, K., H. Matsuda, Y. Okita, and M. Murakami. 2002. Aeruginoguanidines 98-A-98-C: cytotoxic unusual peptides from, the cyanobacterium Microcystis aeruginosa. Tetrahedron 58:7645-7652.
11. Ishida, K., H. Matsuda, M. Murakami, and K. Yamaguchi. 1997. Kawaguchipeptin B, an antibacterial cyclic undecapeptide from the cyanobacterium Microcystis aeruginosa. J. Nat. Prod. 60:724-726.
12. Kotai, J. 1972. Instructions for preparation of modified nutrient solution Z8 for algae. Norwegian Institute for Water Research, Oslo, Norway.
13. Lee, S. W., D. A. Mitchell, A. L. Markley, M. E. Hensler, D. Gonzalez, A. Wohlrab, P. C. Dorrestein, V. Nizet, and J. E. Dixon. 2008. Discovery of a widely distributed toxin biosynthetic gene cluster. Proc. Natl. Acad. Sci. U. S. A. 105:5879-5884.
14. Leikoski, N., D. P. Fewer, and K. Sivonen. 2009. Widespread occurrence and lateral transfer of the cyanobactin biosynthetic gene cluster in cyanobacteria. Appl. Environ. Microbiol. 75:853-857.
15. Magarvey, N. A., Z. Q. Beck, T. Golakati, Y. Ding, U. Huber, T. K. Hemscheidt, D. Abelson, R. E. Moore, and D. H. Sherman. 2006. Biosynthetic characterization, and chemoenzymatic assembly of the cryptophycins. Potent anticancer agents from cyanobionts. ACS Chem. Biol. 1:766-779.
16. Murakami, M., Y. Itou, K. Ishida, and H. J. Shin. 1999. Prenylagaramides A and B, new cyclic peptides from two strains of Oscillatoria agardhii. J. Nat. Prod. 62:752-755.
17. Pomilio, A. B., M. E. Battista, and A. A. Vitale. 2006. Naturally-occurring cyclopeptides: structures and bioactivity. Curr. Org. Chem. 10:2075-2121.
18. Salvatella, X., J. M. Caba, F. Albericio, and E. Giralt. 2003. Solution structure of the antitumor candidate trunkamide A by 2D NMR and restrained simulated annealing methods. J. Org. Chem. 68:211-215.
19. Saska, I., A. D. Gillon, N. Hatsugai, R. G. Dietzgen, I. Hara-Nishimura, M. A. Anderson, and D. J. Craik. 2007. An asparaginyl endopeptidase mediates in vivo protein backbone cyclization. J. Biol. Chem. 282:29721.-29728.
20. Schmidt, E. W., J. T. Nelson, D. A. Rasko, S. Sudek, J. A. Eisen, M. G. Haygood, and J. Ravel. 2005. Patellamide A and C biosynthesis by a microcin-like pathway in Prochloron didemni, the cyanobacterial symbiot of Lissoclinum patella. Proc. Natl. Acad. Sci. U. S. A. 102:7315-7320.
21. Schultz, A. W., D.-C. Oh, J. R. Carney, R. T. Williamson, D. W. Udwary, P. R. Jensen, S. J. Gould, W. Fenical, and B. S. Moore. 2008. Biosynthesis and structures of cyclomarins and cyclomarazines, prenylated cyclic peptides of marine actinobacterial origin. J. Am. Chem. Soc. 130:4507-4516.
22. Shin, H. J., H. Matsuda, M. Murakami, and K. Yamaguchi. 1996. Agardhipeptins A and B, two new cyclic hepta- and octapeptides, from, the cyanobacterium. Oscillatoria agardhii (NIES-204). Tetrahedron 52:13129-13136.
23. Sivonen, K., and T. Börner. 2008. Bioactive compounds produced by cyanobacteria, p. 159-197. In A. Herraro and E. Flores (ed.), The cyanobacteria: molecular biology, genomics and evolution. Caister Academic Press, Norfolk, United Kingdom.
24. Sudek, S., M. G. Haygood, D. T. A. Youssef, and E. W. Schmidt. 2006. Structure of trichamide, a cyclic peptide from the bloom-forming cyanobacterium Trichodesmium erythraeum, predicted from, the genome sequence. Appl. Environ. Microbiol. 72:4382-4387.
25. Tan, N. H., and J. Zhou. 2006. Plant cyclopeptides. Chem. Rev. 106:840-895.
26. Welker, M., and H. von Döhren. 2006. Cyanobacterial peptides-nature's own combinatorial biosynthesis. FEMS Microbiol. Rev. 30:530-563.
27. Ziemert, N., K. Ishida, A. Liaimer, C. Hertweck, and E. Dittmann. 2008. Ribosomal synthesis of tricyclic depsipeptides in bloom-forming cyanobacteria. Angew. Chem. Int. Ed. Engl. 47:7756-7759.
28. Ziemert, N., K. Ishida, P. Quillardet, C. Bouchier, C. Hertweck, N. Tandeau de Marsac, and E. Dittmann. 2008. Microcyclamide biosynthesis in two strains of Microcystis aeruginosa: from structure to genes and vice versa. Appl. Environ. Microbiol. 74:1791-1797.