Two Alternative Starter Modules for the Non-Ribosomal Biosynthesis of Specific Anabaenopeptin Variants in Anabaena (Cyanobacteria)

Chemistry and Biology

Volumn 17, Issue 3, 2010, Pages 265-273

  Rouhiainen, Leo ^a   Jokela, Jouni ^a   Fewer, David P ^a   Urmann, Marina ^a   Sivonen, Kaarina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

CHEMBIO

Indexed keywords

BACTERIAL DNA; BACTERIAL PROTEIN; CYCLOPEPTIDE; PEPTIDE SYNTHASE;

ANABAENA; ARTICLE; BIOSYNTHESIS; CHEMISTRY; ENZYMOLOGY; GENETICS; MASS SPECTROMETRY; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; NONRIBOSOMAL PEPTIDE SYNTHESIS; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; POLYMERASE CHAIN REACTION; PROTEIN MOTIF;

AMINO ACID MOTIFS; ANABAENA; BACTERIAL PROTEINS; BASE SEQUENCE; DNA, BACTERIAL; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; OPEN READING FRAMES; PEPTIDE BIOSYNTHESIS, NUCLEIC ACID-INDEPENDENT; PEPTIDE SYNTHASES; PEPTIDES, CYCLIC; POLYMERASE CHAIN REACTION;

ANABAENA; ANABAENA CIRCINALIS 90; CYANOBACTERIA; NODULARIA; NOSTOC;

EID: 77949546759     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2010.01.017     Document Type: Article

References (40)

1. Altschul S.F., Gish W., Miller W., Meyers E.W., and Lipman D.J. Basic local alignment search tool. J. Mol. Biol. 215 (1990) 403-410
2. Amrein H., Makart S., Granado J., Shakya R., Schneider-Pokorny J., and Dudler R. Functional analysis of genes involved in the synthesis of syringolin A by Pseudomonas syringae pv. syringae B301D-R. Mol. Plant Microbe Interact. 17 (2004) 90-97
3. Bubik A., Sedmak B., Novinec M., Lenarcic B., and Lah T.T. Cytotoxic and peptidase inhibitory activities of selected non-hepatotoxic cyclic peptides from cyanobacteria. Biol. Chem. 389 (2008) 1339-1346
4. Burja A.M., Banaigs B., Abou-Mansour E., Burgess J.G., and Wright P.C. Marine cyanobacteria: a prolific source of natural products. Tetrahedron 57 (2001) 9347-9377
5. Feil H., Feil W.S., Chain P., Larimer F., DiBartolo G., Copeland A., Lykidis A., Trong S., Nolan M., Goltsman E., et al. Comparison of the complete genome sequences of Pseudomonas syringae pv. syringae B728a and pv. tomato DC3000. Proc. Natl. Acad. Sci. USA 102 (2005) 11064-11069
6. Fewer D.P., Rouhiainen L., Jokela J., Wahlsten M., Laakso K., Wang H., and Sivonen K. Recurrent adenylation domain replacement in the microcystin synthetase gene cluster. BMC Evol. Biol. 7 (2007) 183
7. Fewer D.P., Jokela J., Rouhiainen L., Wahlsten M., Koskenniemi K., Stal L., and Sivonen K. The non-ribosomal assembly and frequent occurrence of the protease inhibitors spumigins in the bloom-forming cyanobacterium Nodularia spumigena. Mol. Microbiol. 73 (2009) 924-937
8. Finking R., and Marahiel M.A. Biosynthesis of nonribosomal peptides. Annu. Rev. Microbiol. 58 (2004) 453-488
9. Fujii K., Sivonen K., Nakano T., and Harada K.-I. Structural elucidation of cyanobacterial peptides encoded by peptide synthetase gene in Anabaena species. Tetrahedron 58 (2002) 6863-6871
10. Golden J.W., Carrasco C.D., Mulligan M.E., Scneider G.J., and Haselkorn R. Deletion of a 55-kilobase-pair DNA element from the chromosome during heterocyst differentiation of Anabaena sp. strain PCC 7120. J. Bacteriol. 170 (1988) 5034-5041
11. Grach-Pogrebinsky O., and Carmeli S. Three novel anabaenopeptins from the cyanobacterium Anabaena sp. Tetrahedron 64 (2008) 10233-10238
12. Gruenewald S., Mootz H.D., Stehmeier P., and Stachelhaus T. In vivo production of artificial nonribosomal peptide products in the heterologous host Escherichia coli. Appl. Environ. Microbiol. 70 (2004) 3282-3291
13. Harada K., Fujii K., Shimada T., Suzuki M., Sano H., Adachi K., and Carmichael W.W. Two cyclic peptides, anabaenopeptins, a third group of bioactive compounds from the cyanobacterium Anabaena flos-aquae NRC 525-17. Tetrahedron Lett. 36 (1995) 1511-1514
14. Imker H.J., Walsh C.T., and Wuest W.M. SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor syringolin A. J. Am. Chem. Soc. 191 (2009) 18263-18265
15. Itou Y., Suzuki S., Ishida K., and Murakami M. Anabaenopeptins G and H, potent carboxypeptidase A inhibitors from the cyanobacterium Oscillatoria agardhii (NIES-595). Bioorg. Med. Chem. Lett. 9 (1999) 1243-1246
16. Kotai J. Instructions for Preparation of Modified Nutrient Solution Z8 for Algae. Publication B-11/69, Norwegian Institute for Water Research (1972), Blindern, Oslo
17. Lautru S., and Challis G.L. Substrate recognition by nonribosomal peptide synthetase multi-enzymes. Microbiology 150 (2004) 1629-1636
18. Lawen A., and Traber R. Substrate specificities of cyclosporin synthetase and peptolide SDZ 214-103 synthetase. Comparison of the substrate specificities of the related multifunctional polypeptides. J. Biol. Chem. 268 (1993) 20452-20465
19. Marahiel M.A., Stachelhaus T., and Mootz H.D. Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 97 (1997) 2651-2673
20. Moore R.E. Cyclic peptides and depsipeptides from cyanobacteria: a review. J. Ind. Microbiol. 16 (1996) 134-143
21. Murakami M., Suzuki S., Itou Y., Kodani S., and Ishida K. New anabaenopeptins, potent carboxypeptidase-A inhibitors from the cyanobacterium Aphanizomenon flos-aquae. J. Nat. Prod. 63 (2000) 1280-1282
22. Namikoshi M., and Rinehart K.L. Bioactive compounds produced by cyanobacteria. J. Ind. Microbiol. 17 (1996) 373-384
23. Pearson W.R., and Lipman D.J. Improved tools for biological sequence comparison. Proc. Natl. Acad. Sci. USA 85 (1988) 2444-2448
24. Ramel C., Tobler M., Meyer M., Bigler L., Ebert M.-O., Schellenberg B., and Dudler R. Biosynthesis of the proteasome inhibitor syringolin A: the ureido group joining two amino acids originates from bicarbonate. BMC Biochem. 10 (2009) 26
25. Rausch C., Weber T., Kohlbacher O., Wohlleben W., and Huson D.H. Specificity prediction of adenylation domains in nonribosomal peptide synthetases (NRPS) using Transductive Support Vector Machines (TSVM). Nucleic Acids Res. 33 (2005) 5799-5808
26. Repka S., Koivula M., Harjunpää V., Rouhiainen L., and Sivonen K. Effects of phosphate and light on growth and bioactive peptide production of a cyanobacterium, Anabaena strain 90 and its anabaenopeptilide-mutant. Appl. Environ. Microbiol. 70 (2004) 4551-4560
27. Rice P., Longden I., and Bleasby A. EMBOSS: The European Molecular Biology Open Software Suite. Trends Genet. 16 (2000) 276-277
28. Rippka R., Deruelles J., Waterbury J.B., Herdman M., and Stanier R.Y. Generic assignments, strain histories and properties of pure cultures of cyanobacteria. J. Gen. Microbiol. 111 (1979) 1-61
29. Rouhiainen L., Sivonen K., Buikema W.J., and Haselkorn R. Characterization of toxin-producing cyanobacteria by using an oligonucleotide probe containing a tandemly repeated heptamer. J. Bacteriol. 177 (1995) 6021-6026
30. Rouhiainen L., Paulin L., Suomalainen S., Hyytiäinen H., Buikema W.J., Haselkorn R., and Sivonen K. Genes encoding synthetases of cyclic depsipeptides, anabaenopeptilides, in Anabaena strain 90. Mol. Microbiol. 37 (2000) 156-167
31. Rouhiainen L., Vakkilainen T., Lumbye Siemer B., Buikema W.J., Haselkorn R., and Sivonen K. Genes coding for the synthesis of hepatotoxic heptapeptides (microcystins) in the cyanobacterium Anabaena strain 90. Appl. Environ. Microbiol. 70 (2004) 686-692
32. Rounge T.B., Rohrlack T., Nederbragt A.J., Kristensen T., and Jakobsen K.S. A genome-wide analysis of nonribosomal peptide synthetase gene clusters and their peptides in a Planktothrix rubescens strain. BMC Genomics 10 (2009) 396
33. Sano T., Usui T., Ueda K., Osada H., and Kaya K. Isolation of new protein phosphatase inhibitors from two cyanobacteria species, Planktothrix spp. J. Nat. Prod. 64 (2001) 1052-1055
34. Stachelhaus T., Mootz H.D., and Marahiel M.A. The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem. Biol. 6 (1999) 493-505
35. Sieber S.A., and Marahiel M.A. Molecular mechanisms underlying nonribosomal peptide synthesis: approaches to new antibiotics. Chem. Rev. 105 (2005) 715-738
36. Sivonen K., and Börner T. Bioactive compounds produced by cyanobacteria. In: Herrero A., and Flores E. (Eds). The Cyanobacteria: Molecular Biology, Genomics and Evolution (2008), Caister Academic Press, Linton, UK 159-197
37. Thompson J.D., Higgins D.G., and Gibson T.J. 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 (1994) 4673-4680
38. von Döhren H., Keller U., Vater J., and Zocher R. Multifunctional peptide synthetases. Chem. Rev. 97 (1997) 2675-2705
39. Welker M., and von Döhren H. Cyanobacterial peptides-Nature's own combinatorial biosynthesis. FEMS Microbiol. Rev. 30 (2006) 530-563
40. Zdobnov E.M., and Apweiler R. InterProScan - an integration platform for the signature-recognition methods in InterPro. Bioinformatics 17 (2001) 847-848