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Volumn 149, Issue 4, 2011, Pages 475-485

Characterization of the locus of genes encoding enzymes producing heptadepsipeptide micropeptin in the unicellular cyanobacterium Microcystis

Author keywords

cyanobacteria; halogenase; Microcystis; micropeptin; non ribosomal peptide synthetase

Indexed keywords

CYCLOPEPTIDE; DEPSIPEPTIDE; HEPTADEPSIPEPTIDE MICROPEPTIN; NONRIBOSOMAL PEPTIDE SYNTHETASE; PEPTIDE SYNTHASE; UNCLASSIFIED DRUG;

EID: 79953197562     PISSN: 0021924X     EISSN: 17562651     Source Type: Journal    
DOI: 10.1093/jb/mvq150     Document Type: Article
Times cited : (30)

References (44)
  • 1
    • 0027482363 scopus 로고
    • Cyanopeptolins, new depsipeptides from the cyanobacterium Microcystis sp. PCC 7806
    • Martin, C., Oberer, L., Ino, T., Konig, W.A., Busch, M., and Weckesser, J. (1993) Cyanopeptolins, new depsipep-tides from the cyanobacterium Microcystis sp. PCC 7806. J. Antibiot. 46, 1550-1556 (Pubitemid 23324894)
    • (1993) Journal of Antibiotics , vol.46 , Issue.10 , pp. 1550-1556
    • Martin, C.1    Oberer, L.2    Ino, T.3    Konig, W.A.4    Busch, M.5    Weckesser, J.6
  • 2
    • 0033582989 scopus 로고    scopus 로고
    • Micropeptin T-20, a novel phosphate-containing cyclic depsipeptide from the cyanobacterium Microcystis aeruginosa
    • DOI 10.1016/S0040-4039(99)00193-8, PII S0040403999001938
    • Okano, T., Sano, T., and Kaya, K. (1999) Micropeptin T-20, a novel phosphate-containing cyclic depsipeptide from the cyanobacterium Microcystis aeruginosa. Tetrahedron Lett. 40, 2379-2382 (Pubitemid 29113153)
    • (1999) Tetrahedron Letters , vol.40 , Issue.12 , pp. 2379-2382
    • Okano, T.1    Sano, T.2    Kaya, K.3
  • 3
    • 0037136374 scopus 로고    scopus 로고
    • Structural elucidation of cyanobacterial peptides encoded by peptide synthetase gene in Anabaena species
    • DOI 10.1016/S0040-4020(02)00747-0, PII S0040402002007470
    • Fujii, K., Sivonen, K., Nakano, T., and Harada, K.-I. (2002) Structural elucidation of cyanobacterial peptides encoded by peptide synthetase gene in Anabaena species. Tetrahedron 58, 6863-6871 (Pubitemid 35266622)
    • (2002) Tetrahedron , vol.58 , Issue.34 , pp. 6863-6871
    • Fujii, K.1    Sivonen, K.2    Nakano, T.3    Harada, K.-I.4
  • 4
    • 33744965454 scopus 로고    scopus 로고
    • Cyanobacterial peptides - Nature's own combinatorial biosynthesis
    • DOI 10.1111/j.1574-6976.2006.00022.x
    • Welker, M. and von Dohren, H. (2006) Cyanobacterial peptides-nature's own combinatorial biosynthesis. FEMS Microbiol. Rev. 30, 530-563 (Pubitemid 43855766)
    • (2006) FEMS Microbiology Reviews , vol.30 , Issue.4 , pp. 530-563
    • Welker, M.1    Von Dohren, H.2
  • 5
    • 0030484901 scopus 로고    scopus 로고
    • Bioactive compounds produced by cyanobacteria
    • Namikoshi, M. and Rinehart, K.L. (1996) Bioactive compounds produced by cyanobacteria. J. Ind. Microbiol. 17, 373-384
    • (1996) J. Ind. Microbiol. , vol.17 , pp. 373-384
    • Namikoshi, M.1    Rinehart, K.L.2
  • 7
    • 34249090193 scopus 로고    scopus 로고
    • Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon from Microcystis: Implications for evolution of cyanopeptolins
    • DOI 10.1099/mic.0.2006/001123-0
    • Tooming-Klunderud, A., Rohrlack, T., Shalchian-Tabrizi, K., Kristensen, T., and Jakobsen, K.S. (2007) Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon form Microcystis: implications for evolution of cyanopeptolins. Microbiology 153, 1382-1393 (Pubitemid 46779994)
    • (2007) Microbiology , vol.153 , Issue.5 , pp. 1382-1393
    • Tooming-Klunderud, A.1    Rohrlack, T.2    Shalchian-Tabrizi, K.3    Kristensen, T.4    Jakobsen, K.S.5
  • 8
    • 0028518887 scopus 로고
    • Atomic structure of the trypsin-A90720A com-plex: A unified approach to structure and function
    • Lee, A.Y., Smitka, T.A., Bonjouklian, R., and Clardy, J. (1994) Atomic structure of the trypsin-A90720A com-plex: a unified approach to structure and function. Chem. Biol. 1, 113-117
    • (1994) Chem. Biol. , vol.1 , pp. 113-117
    • Lee, A.Y.1    Smitka, T.A.2    Bonjouklian, R.3    Clardy, J.4
  • 9
    • 0027133116 scopus 로고
    • Micropeptins A and B, plasmin and trypsin inhibitors from the blue-green alga Microcystis aeruginosa
    • Okino, T., Murakami, M., Haraguchi, R., Munekata, H., Matsuda, H., and Yamaguchi, K. (1993) Micropeptins A and B, plasmin and trypsin inhibitors from the blue-green alga Microcystis aeruginosa. Tetrahedron Lett 34, 8131-8134
    • (1993) Tetrahedron Lett , vol.34 , pp. 8131-8134
    • Okino, T.1    Murakami, M.2    Haraguchi, R.3    Munekata, H.4    Matsuda, H.5    Yamaguchi, K.6
  • 10
    • 42049111878 scopus 로고    scopus 로고
    • Secondary metabolites from cyanobacteria: Complex structures and powerful bioactivities
    • Gademann, K. and Portmann, C. (2008) Secondary metabolites from cyanobacteria: complex structures and powerful bioactivities. Curr. Org. Chem. 12, 326-341
    • (2008) Curr. Org. Chem. , vol.12 , pp. 326-341
    • Gademann, K.1    Portmann, C.2
  • 12
    • 0031215148 scopus 로고    scopus 로고
    • Protein templates for the biosynthesis of peptide antibiotics
    • Marahiel, M.A. (1997) Protein templates for the biosyn-thesis of peptide antibiotics. Chem. Biol. 4, 561-567 (Pubitemid 27398759)
    • (1997) Chemistry and Biology , vol.4 , Issue.8 , pp. 561-567
    • Marahiel, M.A.1
  • 13
    • 0032873121 scopus 로고    scopus 로고
    • Genetic analysis of the peptide synthetase genes for a cyclic heptapeptide microcystin in Microcystis spp
    • Nishizawa, T., Asayama, M., Fujii, 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 (Pubitemid 29452616)
    • (1999) Journal of Biochemistry , vol.126 , Issue.3 , pp. 520-529
    • Nishizawa, T.1    Asayama, M.2    Fujii, K.3    Harada, K.-I.4    Shirai, M.5
  • 14
    • 0034115536 scopus 로고    scopus 로고
    • Polyketide synthase gene coupled to the peptide synthetase module involved in the biosynthesis of the cyclic heptapeptide microcystin
    • Nishizawa, T., Ueda, A., Asayama, M., Fujii, K., Harada, K.-I., Ochi, K., and Shirai, M. (2000) Polyketide synthase gene coupled to the peptide synthe-tase module involved in the biosynthesis of the cyclic heptapeptide microcystin. J. Biochem. 127, 779-789 (Pubitemid 30317901)
    • (2000) Journal of Biochemistry , vol.127 , Issue.5 , pp. 779-789
    • Nishizawa, T.1    Ueda, A.2    Asayama, M.3    Fujii, K.4    Harada, K.-I.5    Ochi, K.6    Shirai, M.7
  • 15
    • 0033780306 scopus 로고    scopus 로고
    • Structural organization of microcystin biosynthesis in Microcystis aeruginosa PCC7806: An integrated peptide-polyketide synthetase system
    • Tillett, D., Dittmann, E., Erhard, M., von Dohren, H., Borner, T., and Neilan, B.A. (2000) Structural organization of microcystin biosynthesis in Microcystis aeruginosa PCC7806: an integrated peptide-polyketide synthetase system. Chem. Biol. 7, 753-764
    • (2000) Chem. Biol. , vol.7 , pp. 753-764
    • Tillett, D.1    Dittmann, E.2    Erhard, M.3    Von Dohren, H.4    Borner, T.5    Neilan, B.A.6
  • 16
    • 0037226538 scopus 로고    scopus 로고
    • Microcystin biosynthesis in Planktothrix: Genes, evolution, and manipulation
    • DOI 10.1128/JB.185.2.564-572.2003
    • Christiansen, G., Fastner, J., Erhard, M., Borner, T., and Dittmann, E. (2003) Microcystin biosynthesis in Planktothrix: genes, evolution, and manipulation. J. Bacteriol. 185, 564-572 (Pubitemid 36070483)
    • (2003) Journal of Bacteriology , vol.185 , Issue.2 , pp. 564-572
    • Christiansen, G.1    Fastner, J.2    Erhard, M.3    Borner, T.4    Dittmann, E.5
  • 18
    • 51149094258 scopus 로고    scopus 로고
    • Diversity within the micro-cystin biosynthetic gene clusters among the genus Microcystis
    • Nishizawa, T., Nishizawa, A., Asayama, M., Harada, K.-I., and Shirai, M. (2007) Diversity within the micro-cystin biosynthetic gene clusters among the genus Microcystis. Microbes Environ. 22, 380-390
    • (2007) Microbes Environ. , vol.22 , pp. 380-390
    • Nishizawa, T.1    Nishizawa, A.2    Asayama, M.3    Harada, K.-I.4    Shirai, M.5
  • 21
    • 0033926435 scopus 로고    scopus 로고
    • Genes encoding synthetases of cyclic depsipeptides, anabaenopeptilides, in Anabaena strain 90
    • DOI 10.1046/j.1365-2958.2000.01982.x
    • Rouhiainen, L., Paulin, L., Suomalainen, S., Hyytianen, H., Buikema, W., Haselkorn, R., and Sivonen, K. (2000) Genes encoding synthetases of cyclic depsipeptides, ana-baenopeptilides, in Anabaena strain 90. Mol. Microbiol. 37, 156-167 (Pubitemid 30479365)
    • (2000) Molecular Microbiology , vol.37 , Issue.1 , pp. 156-167
    • Rouhiainen, L.1    Paulin, L.2    Suomalainen, S.3    Hyytiainen, H.4    Buikema, W.5    Haselkorn, R.6    Sivonen, K.7
  • 22
    • 36649038371 scopus 로고    scopus 로고
    • Comparison of cyanopeptolin genes in Planktothrix, Microcystis, and Anabaena strains: Evidence for independent evolution within each genus
    • DOI 10.1128/AEM.01475-07
    • Rounge, T.B., Rohrlack, T., Tooming-Klunderud, A., Kristensen, T., and Jakobsen, K.S. (2007) Comparison of cyanopeptolin genes in Planktothrix, Microcystis, and Anabaena strains: evidence for independent evolution within each genus. Appl. Environ. Microbiol. 73, 7322-7330 (Pubitemid 350196683)
    • (2007) Applied and Environmental Microbiology , vol.73 , Issue.22 , pp. 7322-7330
    • Rounge, T.B.1    Rohrlack, T.2    Tooming-Klunderud, A.3    Kristensen, T.4    Jakobsen, K.S.5
  • 25
    • 1542328831 scopus 로고    scopus 로고
    • Comprehensive analysis system using liquid chromatography-mass spectrometry for the biosynthetic study of peptides produced by cyanobacteria
    • DOI 10.1016/j.chroma.2004.01.006, PII S0021967304000482
    • Harada, K.-I., Nakano, T., Fujii, K., and Shirai, M. (2004) Comprehensive analysis system using liquid chromatography-mass spectrometry for the biosynthetic study of peptides produced by cyanobacteria. J. Chromat. A 1033, 107-113 (Pubitemid 38317012)
    • (2004) Journal of Chromatography A , vol.1033 , Issue.1 , pp. 107-113
    • Harada, K.-I.1    Nakano, T.2    Fujii, K.3    Shirai, M.4
  • 26
    • 34248210095 scopus 로고    scopus 로고
    • Cloning and characterization of a new hetero-gene cluster of nonribosomal peptide synthetase and polyketide synthase from the cyanobacterium Microcystis aeruginosa K-139
    • DOI 10.2323/jgam.53.17
    • Nishizawa, A., Arshad, A. B., Nishizawa, T., Asayama, M., Fujii, K., Nakano, T., Harada, K.-I., and Shirai, M. (2007) Cloning and characterization ofanew hetero-gene cluster of nonribosomal peptide synthetase and polyke-tide synthase from the cyanobacterium Microcystis aeruginosa K-139. J. Gen. Appl. Microbiol. 53, 17-27 (Pubitemid 351659027)
    • (2007) Journal of General and Applied Microbiology , vol.53 , Issue.1 , pp. 17-27
    • Nishizawa, A.1    Arshad, A.B.2    Nishizawa, T.3    Asayama, M.4    Fujii, K.5    Nakano, T.6    Harada, K.-I.7    Shirai, M.8
  • 29
    • 0025758255 scopus 로고
    • Toxicity and toxins of natural blooms and isolated of Microcystis spp. (cyanobacteria) and improved procedure for purifi-cation of cultures
    • Shirai, M., Ohtake, A., Sano, T., Matsumoto, S., Sakamoto, T., Sato, A., Aida, T., Harada, K., Shimada, T., and Suzuki, M. (1991) Toxicity and toxins of natural blooms and isolated of Microcystis spp. (cyanobacteria) and improved procedure for purifi-cation of cultures. Appl. Environ. Microbiol. 57, 1241-1245
    • (1991) Appl. Environ. Microbiol. , vol.57 , pp. 1241-1245
    • Shirai, M.1    Ohtake, A.2    Sano, T.3    Matsumoto, S.4    Sakamoto, T.5    Sato, A.6    Aida, T.7    Harada, K.8    Shimada, T.9    Suzuki, M.10
  • 30
    • 0001216660 scopus 로고
    • Development of a solid medium for growth and isolation of axenic Microcystis strains (cyanobacteria)
    • Shirai, M., Matsumaru, K., Ohtake, A., Takamura, Y., Aida, T., and Nakano, M. (1989) Development of a solid medium for growth and isolation of axenic Microcystis strains (cyanobacteria). Appl. Environ. Microbiol. 55, 2569-2571
    • (1989) Appl. Environ. Microbiol. , vol.55 , pp. 2569-2571
    • Shirai, M.1    Matsumaru, K.2    Ohtake, A.3    Takamura, Y.4    Aida, T.5    Nakano, M.6
  • 34
    • 0030750386 scopus 로고    scopus 로고
    • Characterization of Gramicidin S synthetase aggregation substance: Control of Gramicidin S synthesis by its product, Gramicidin S
    • Hori, K. and Kurotsu, T. (1997) Characterization of gramicidin S synthetase aggregation substance: control of gramicidin S synthesis by its product, gramicidin S. J. Biochem. 122, 606-615 (Pubitemid 27443239)
    • (1997) Journal of Biochemistry , vol.122 , Issue.3 , pp. 606-615
    • Hori, K.1    Kurotsu, T.2
  • 35
    • 8744220572 scopus 로고    scopus 로고
    • Inactivation of an ABC transporter gene, mcyH, results in loss of microcystin production in the cyanobacterium Microcystis aeruginosa PCC 7806
    • DOI 10.1128/AEM.70.11.6370-6378.2004
    • Pearson, L.A., Hisbergues, M., Borner, T., Dittmann, E., and Neilan, B.A. (2004) Inactivation of an ABC trans-porter gene, mcyH, results in loss of microcystin produc-tion in the cyanobacterium Microcystis aeruginosa PCC 7806. Appl. Environ. Microbiol. 70, 6370-6378 (Pubitemid 39518539)
    • (2004) Applied and Environmental Microbiology , vol.70 , Issue.11 , pp. 6370-6378
    • Pearson, L.A.1    Hisbergues, M.2    Borner, T.3    Dittmann, E.4    Neilan, B.A.5
  • 36
    • 0033179468 scopus 로고    scopus 로고
    • The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases
    • DOI 10.1016/S1074-5521(99)80082-9
    • 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 (Pubitemid 29380764)
    • (1999) Chemistry and Biology , vol.6 , Issue.8 , pp. 493-505
    • Stachelhaus, T.1    Mootz, H.D.2    Marahiel, M.A.3
  • 37
    • 0034013269 scopus 로고    scopus 로고
    • Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains
    • DOI 10.1016/S1074-5521(00)00091-0
    • Challis, G.L., Ravel, J., and Townsend, CA. (2000) Predictive, structure-based model of amino acid recogni-tion by nonribosomal peptide synthetase adenylation domains. Chem. Biol. 7, 211-224 (Pubitemid 30147205)
    • (2000) Chemistry and Biology , vol.7 , Issue.3 , pp. 211-224
    • Challis, G.L.1    Ravel, J.2    Townsend, C.A.3
  • 38
    • 0030589120 scopus 로고    scopus 로고
    • Restriction barrier composed of an extracellular nuclease and restriction endonuclease in the unicellular cyanobacterium Microcystis sp
    • DOI 10.1016/0378-1097(96)00395-3, PII S0378109796003953
    • Takahashi, I., Hayano, D., Asayama, M., Masahiro, F., Watahiki, M., and Shirai, M. (1996) Restriction barrier composed of an extracellular nuclease and restriction endonuclease in the unicellular cyanobacterium Microcystis sp. FEMS Microbiol. Lett. 145, 107-111 (Pubitemid 26366697)
    • (1996) FEMS Microbiology Letters , vol.145 , Issue.1 , pp. 107-111
    • Takahashi, I.1    Hayano, D.2    Asayama, M.3    Masahiro, F.4    Watahiki, M.5    Shirai, M.6
  • 39
    • 0035016977 scopus 로고    scopus 로고
    • Cyclic heptapeptide microcystin biosynthesis requires the glutamate racemase gene
    • Nishizawa, T., Asayama, M., and Shirai, M. (2001) Cyclic heptapeptide microcystin biosynthesis requires the glutamate racemase gene. Microbiology 147, 1235-1241 (Pubitemid 32454641)
    • (2001) Microbiology , vol.147 , Issue.5 , pp. 1235-1241
    • Nishizawa, T.1    Asayama, M.2    Shirai, M.3
  • 40
    • 33646816419 scopus 로고    scopus 로고
    • Flavin-dependent halogenases involved in secondary metabolism in bacteria
    • DOI 10.1007/s00253-005-0232-2
    • vanPee, K.H. and Patallo, E.P. (2006) Flavin-dependent halogenases involved in secondary metabolism in bac-teria. Appl. Microbiol. Biotechnol. 70, 631-641 (Pubitemid 43760498)
    • (2006) Applied Microbiology and Biotechnology , vol.70 , Issue.6 , pp. 631-641
    • Van Pee, K.-H.1    Patallo, E.P.2
  • 41
    • 49749108516 scopus 로고    scopus 로고
    • Halogenase genes in nonribosomal peptide synthetase gene clusters of Microcystis (cyanobacteria): Sporadic distribution and evolution
    • Cadel-Six, S., Dauga, C., Castets, A.M., Rippka, R., Bouchier, C., Tandeau de Marsac, N., and Welker, M. (2008) Halogenase genes in nonribosomal peptide synthetase gene clusters of Microcystis (cyanobacteria): sporadic distribution and evolution. Mol. Biol. Evol. 25, 2031-2041
    • (2008) Mol. Biol. Evol. , vol.25 , pp. 2031-2041
    • Cadel-Six, S.1    Dauga, C.2    Castets, A.M.3    Rippka, R.4    Bouchier, C.5    Tandeau De Marsac, N.6    Welker, M.7
  • 43
    • 0031018804 scopus 로고    scopus 로고
    • Micropeptins 478-A and -B, plasmin inhibitors from the cyanobacterium Microcystis aeruginosa
    • DOI 10.1021/np9606815
    • Ishida, K., Matsuda, H., Murakami, M., and Yamaguchi, K. (1997) Micropeptins 478-A and-B, plas-min inhibitors from the cyanobacterium Microcystis aeruginosa. J. Nat. Prod. 60, 184-187 (Pubitemid 27098571)
    • (1997) Journal of Natural Products , vol.60 , Issue.2 , pp. 184-187
    • Ishida, K.1    Matsuda, H.2    Murakami, M.3    Yamaguchi, K.4
  • 44
    • 0030933127 scopus 로고    scopus 로고
    • Micropeptin 103, a chymotrypsin inhibitor from the cyanobacterium Microcystis viridis (NIES-103)
    • DOI 10.1016/S0040-4039(97)00528-5, PII S0040403997005285
    • Murakami, M., Kodani, S., Ishida, K., Matsuda, H., and Yamaguchi, K. (1997) Micropeptin 103, a chymotrypsin inhibitor from the cyanobacterium Microcystis viridis (NIES-103). Tetrahedron Lett. 38, 3035-3038 (Pubitemid 27180259)
    • (1997) Tetrahedron Letters , vol.38 , Issue.17 , pp. 3035-3038
    • Murakami, M.1    Kodani, S.2    Ishida, K.3    Matsuda, H.4    Yamaguchi, K.5


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