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Volumn 9, Issue 2, 2014, Pages 372-377

Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua

Author keywords

[No Author keywords available]

Indexed keywords

3 ( 2' ISOCYANOETHENYL)INDOLE; AMBIGUINE; AMBIGUINE A; CARBON; DIMETHYLALLYLTRANSFERASE; ENZYME; GERANYL PYROPHOSPHATE; HAPALINDOLE G; HYDROGEN; INDOLE ALKALOID; INDOLE DERIVATIVE; INDOLE DIMETHYLALLYLTRANSFERASE; NATURAL PRODUCT; PYROPHOSPHATE; UNCLASSIFIED DRUG;

EID: 84896690506     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400681n     Document Type: Article
Times cited : (89)

References (31)
  • 1
    • 0001598577 scopus 로고
    • Hapalindoles: New alkaloids from the blue-green alga Hapalosiphon fontinalis
    • Moore, R. E., Cheuk, C., and Patterson, G. M. L. (1984) Hapalindoles: New alkaloids from the blue-green alga Hapalosiphon fontinalis J. Am. Chem. Soc. 106, 6456-6457
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6456-6457
    • Moore, R.E.1    Cheuk, C.2    Patterson, G.M.L.3
  • 4
    • 0026725094 scopus 로고
    • Fischerindole L, a new isonitrile from the terrestrial blue-green alga Fischerella muscicola
    • Park, A., Moore, R. E., and Patterson, G. M. L. (1992) Fischerindole L, a new isonitrile from the terrestrial blue-green alga Fischerella muscicola Tetrahedron Lett. 33, 3257-3260
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3257-3260
    • Park, A.1    Moore, R.E.2    Patterson, G.M.L.3
  • 5
    • 0027973653 scopus 로고
    • Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and Westiella intricata. Relationship to fischerindoles and hapalinodoles
    • Stratmann, K., Moore, R. E., Bonjouklian, R., Deeter, J. B., Patterson, G. M. L., Shaffer, S., Smith, C. D., and Smitka, T. A. (1994) Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and Westiella intricata. Relationship to fischerindoles and hapalinodoles J. Am. Chem. Soc. 116, 9935-9942
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9935-9942
    • Stratmann, K.1    Moore, R.E.2    Bonjouklian, R.3    Deeter, J.B.4    Patterson, G.M.L.5    Shaffer, S.6    Smith, C.D.7    Smitka, T.A.8
  • 6
    • 33947363667 scopus 로고    scopus 로고
    • Antimicrobial ambiguines from the cyanobacterium Fischerella sp. Collected in Israel
    • Raveh, A. and Carmeli, S. (2007) Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel J. Nat. Prod. 70, 196-201
    • (2007) J. Nat. Prod. , vol.70 , pp. 196-201
    • Raveh, A.1    Carmeli, S.2
  • 7
    • 66449107185 scopus 로고    scopus 로고
    • Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua
    • Mo, S. Y., Krunic, A., Chlipala, G., and Orjala, J. (2009) Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua J. Nat. Prod. 72, 894-899
    • (2009) J. Nat. Prod. , vol.72 , pp. 894-899
    • Mo, S.Y.1    Krunic, A.2    Chlipala, G.3    Orjala, J.4
  • 8
    • 78249284047 scopus 로고    scopus 로고
    • Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua
    • Mo, S. Y., Krunic, A., Santarsiero, B. D., Franzblau, S. G., and Orjala, J. (2010) Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua Phytochemistry 71, 2116-2123
    • (2010) Phytochemistry , vol.71 , pp. 2116-2123
    • Mo, S.Y.1    Krunic, A.2    Santarsiero, B.D.3    Franzblau, S.G.4    Orjala, J.5
  • 10
    • 0028944619 scopus 로고
    • Welwitindolinone analogues that reverse P-glycoprotein-mediated multiple drug resistance
    • Smith, C. D., Zilfou, J. T., Stratmann, K., Patterson, G. M. L., and Moore, R. E. (1995) Welwitindolinone analogues that reverse P-glycoprotein- mediated multiple drug resistance Mol. Pharmacol. 47, 241-247
    • (1995) Mol. Pharmacol. , vol.47 , pp. 241-247
    • Smith, C.D.1    Zilfou, J.T.2    Stratmann, K.3    Patterson, G.M.L.4    Moore, R.E.5
  • 11
    • 58849128316 scopus 로고    scopus 로고
    • Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach
    • Richter, J. M., Ishihara, Y., Masuda, T., Whitefield, B. W., Llamas, T., Pohjakallio, A., and Baran, P. S. (2008) Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach J. Am. Chem. Soc. 130, 17938-17954
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 17938-17954
    • Richter, J.M.1    Ishihara, Y.2    Masuda, T.3    Whitefield, B.W.4    Llamas, T.5    Pohjakallio, A.6    Baran, P.S.7
  • 12
    • 82355171178 scopus 로고    scopus 로고
    • Evolutionary relationships of microbial aromatic prenyltransferases
    • Bonitz, T., Alva, V., Saleh, O., Lupas, A. N., and Heide, L. (2011) Evolutionary relationships of microbial aromatic prenyltransferases PLoS One 6, e27336-1-e27336-8
    • (2011) PLoS One , vol.6
    • Bonitz, T.1    Alva, V.2    Saleh, O.3    Lupas, A.N.4    Heide, L.5
  • 13
    • 27744497479 scopus 로고    scopus 로고
    • Systematic investigation of the Escherichia coli metabolome for the biosynthetic origin of an isocyanide carbon atom
    • Brady, S. F. and Clardy, J. (2005) Systematic investigation of the Escherichia coli metabolome for the biosynthetic origin of an isocyanide carbon atom Angew. Chem., Int. Ed. 44, 7045-7048
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7045-7048
    • Brady, S.F.1    Clardy, J.2
  • 14
    • 27744453364 scopus 로고    scopus 로고
    • Cloning and heterologous expression of isocyanide biosynthetic genes from environmental DNA
    • Brady, S. F. and Clardy, J. (2005) Cloning and heterologous expression of isocyanide biosynthetic genes from environmental DNA Angew. Chem., Int. Ed. 44, 7063-7065
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7063-7065
    • Brady, S.F.1    Clardy, J.2
  • 15
    • 35048880555 scopus 로고    scopus 로고
    • Natural products from isnA-containing biosynthetic gene clusters recovered from the genomes of cultured and uncultured bacteria
    • Brady, S. F., Bauer, J. D., Clarke-Pearson, M. F., and Daniels, R. (2007) Natural products from isnA-containing biosynthetic gene clusters recovered from the genomes of cultured and uncultured bacteria J. Am. Chem. Soc. 129, 12102-12103
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12102-12103
    • Brady, S.F.1    Bauer, J.D.2    Clarke-Pearson, M.F.3    Daniels, R.4
  • 16
    • 53949092024 scopus 로고    scopus 로고
    • Paerucumarin, a new metabolite produced by the pvc gene cluster from Pseudomonas aeruginosa
    • Clarke-Pearson, M. F. and Brady, S. F. (2008) Paerucumarin, a new metabolite produced by the pvc gene cluster from Pseudomonas aeruginosa J. Bacteriol. 190, 6927-6930
    • (2008) J. Bacteriol. , vol.190 , pp. 6927-6930
    • Clarke-Pearson, M.F.1    Brady, S.F.2
  • 18
    • 84896729403 scopus 로고    scopus 로고
    • F. ambigua UTEX1903 was obtained from the culture collection of algae at the University of Texas at Austin and was rendered axenic by Dr. David R. Nobles, Jr. on Jan 23
    • F. ambigua UTEX1903 was obtained from the culture collection of algae at the University of Texas at Austin and was rendered axenic by Dr. David R. Nobles, Jr. on Jan 23, 2009 (http://web.biosci.utexas.edu/utex/algaeDetail.aspx? algaeID=4360).
    • (2009)
  • 20
    • 0346789056 scopus 로고    scopus 로고
    • Cloning, sequencing, and biochemical characterization of the nostocyclopeptide biosynthetic gene cluster: Molecular basis for imine macrocyclization
    • Becker, J. E., Moore, R. E., and Moore, B. S. (2004) Cloning, sequencing, and biochemical characterization of the nostocyclopeptide biosynthetic gene cluster: Molecular basis for imine macrocyclization Gene 325, 35-42
    • (2004) Gene , vol.325 , pp. 35-42
    • Becker, J.E.1    Moore, R.E.2    Moore, B.S.3
  • 21
    • 79551482320 scopus 로고    scopus 로고
    • Rv0989c encodes a novel (E)-geranyl diphosphate synthase facilitating decaprenyl diphosphate biosynthesis in Mycobacterium tuberculosis
    • Mann, F. M., Thomas, J. A., and Peters, R. J. (2011) Rv0989c encodes a novel (E)-geranyl diphosphate synthase facilitating decaprenyl diphosphate biosynthesis in Mycobacterium tuberculosis FEBS Lett. 585, 549-554
    • (2011) FEBS Lett. , vol.585 , pp. 549-554
    • Mann, F.M.1    Thomas, J.A.2    Peters, R.J.3
  • 23
    • 67649816707 scopus 로고    scopus 로고
    • Aromatic prenylation in phenazine biosynthesis: Dihydrophenazine-1- carboxylate dimethylallyltransferase from Streptomyces anulatus
    • Saleh, O., Gust, B., Boll, B., Fiedler, H. P., and Heide, L. (2009) Aromatic prenylation in phenazine biosynthesis: Dihydrophenazine-1-carboxylate dimethylallyltransferase from Streptomyces anulatus J. Biol. Chem. 284, 14439-14447
    • (2009) J. Biol. Chem. , vol.284 , pp. 14439-14447
    • Saleh, O.1    Gust, B.2    Boll, B.3    Fiedler, H.P.4    Heide, L.5
  • 24
    • 77950377385 scopus 로고    scopus 로고
    • Functional characterization of the cyclomarin/cyclomarazine prenyltransferase CymD directs the biosynthesis of unnatural cyclic peptides
    • Schultz, A. W., Lewis, C. A., Luzung, M. R., Baran, P. S., and Moore, B. S. (2010) Functional characterization of the cyclomarin/cyclomarazine prenyltransferase CymD directs the biosynthesis of unnatural cyclic peptides J. Nat. Prod. 73, 373-377
    • (2010) J. Nat. Prod. , vol.73 , pp. 373-377
    • Schultz, A.W.1    Lewis, C.A.2    Luzung, M.R.3    Baran, P.S.4    Moore, B.S.5
  • 26
    • 84876537991 scopus 로고    scopus 로고
    • Substrate placement influences reactivity in non-heme Fe(II) halogenases and hydroxylases
    • Kulik, H. J. and Drennan, C. L. (2013) Substrate placement influences reactivity in non-heme Fe(II) halogenases and hydroxylases J. Biol. Chem. 288, 11233-11241
    • (2013) J. Biol. Chem. , vol.288 , pp. 11233-11241
    • Kulik, H.J.1    Drennan, C.L.2
  • 27
    • 27744589609 scopus 로고    scopus 로고
    • Reconstitution and characterization of aminopyrrolnitrin oxygenase, a Rieske N-oxygenase that catalyzes unusual arylamine oxidation
    • Lee, J., Simurdiak, M., and Zhao, H. (2005) Reconstitution and characterization of aminopyrrolnitrin oxygenase, a Rieske N-oxygenase that catalyzes unusual arylamine oxidation J. Biol. Chem. 280, 36719-36727
    • (2005) J. Biol. Chem. , vol.280 , pp. 36719-36727
    • Lee, J.1    Simurdiak, M.2    Zhao, H.3
  • 28
    • 79955082670 scopus 로고    scopus 로고
    • Regio- and stereodivergent antibiotic oxidative carbocyclizations catalysed by Rieske oxygenase-like enzymes
    • Sydor, P. K., Barry, S. M., Odulate, O. M., Barona-Gomez, F., Haynes, S. W., Corre, C., Song, L., and Challis, G. L. (2011) Regio- and stereodivergent antibiotic oxidative carbocyclizations catalysed by Rieske oxygenase-like enzymes Nat. Chem. 3, 388-392
    • (2011) Nat. Chem. , vol.3 , pp. 388-392
    • Sydor, P.K.1    Barry, S.M.2    Odulate, O.M.3    Barona-Gomez, F.4    Haynes, S.W.5    Corre, C.6    Song, L.7    Challis, G.L.8
  • 29
    • 84865307505 scopus 로고    scopus 로고
    • Complexity generation during natural product biosynthesis using redox enzymes
    • Wang, P., Gao, X., and Tang, Y. (2012) Complexity generation during natural product biosynthesis using redox enzymes Curr. Opin. Chem. Biol. 16, 362-369
    • (2012) Curr. Opin. Chem. Biol. , vol.16 , pp. 362-369
    • Wang, P.1    Gao, X.2    Tang, Y.3
  • 30
    • 84870925950 scopus 로고    scopus 로고
    • Flavoenzymes: Versatile catalysts in biosynthetic pathways
    • Walsh, C. T. and Wencewicz, T. A. (2013) Flavoenzymes: Versatile catalysts in biosynthetic pathways Nat. Prod. Rep. 30, 175-200
    • (2013) Nat. Prod. Rep. , vol.30 , pp. 175-200
    • Walsh, C.T.1    Wencewicz, T.A.2
  • 31
    • 84868318849 scopus 로고    scopus 로고
    • Diversity of P450 enzymes in the biosynthesis of natural products
    • Podust, L. M. and Sherman, D. H. (2012) Diversity of P450 enzymes in the biosynthesis of natural products Nat. Prod. Rep. 29, 1251-1266
    • (2012) Nat. Prod. Rep. , vol.29 , pp. 1251-1266
    • Podust, L.M.1    Sherman, D.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.