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Volumn 11, Issue 5, 2016, Pages 1287-1295

Characterization of Polyketide Synthase Machinery from the pks Island Facilitates Isolation of a Candidate Precolibactin

Author keywords

[No Author keywords available]

Indexed keywords

ACYL CARRIER PROTEIN; ACYLTRANSFERASE; BACTERIAL TOXIN; MALONYL COENZYME A; POLYKETIDE SYNTHASE; PRECOLIBACTIN; UNCLASSIFIED DRUG; COLIBACTIN; ESCHERICHIA COLI PROTEIN; PEPTIDE; PEPTIDE SYNTHASE; POLYKETIDE;

EID: 84971276185     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.6b00014     Document Type: Article
Times cited : (46)

References (44)
  • 1
    • 84940453070 scopus 로고    scopus 로고
    • The microbes inside us and the race for colibactin
    • Bode, H. B. (2015) The microbes inside us and the race for colibactin Angew. Chem., Int. Ed. 54, 10408-10411 10.1002/anie.201505341
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 10408-10411
    • Bode, H.B.1
  • 2
    • 84945273475 scopus 로고    scopus 로고
    • Colibactin: Understanding an elusive gut bacterial genotoxin
    • Balskus, E. P. (2015) Colibactin: understanding an elusive gut bacterial genotoxin Nat. Prod. Rep. 32, 1534-1540 10.1039/C5NP00091B
    • (2015) Nat. Prod. Rep. , vol.32 , pp. 1534-1540
    • Balskus, E.P.1
  • 4
    • 77954730486 scopus 로고    scopus 로고
    • Escherichia coli induces DNA damage in vivo and triggers genomic instability in mammalian cells
    • Cuevas-Ramos, G., Petit, C. R., Marcq, I., Boury, M., Oswald, E., and Nougayrède, J. (2010) Escherichia coli induces DNA damage in vivo and triggers genomic instability in mammalian cells Proc. Natl. Acad. Sci. U. S. A. 107, 11537-11542 10.1073/pnas.1001261107
    • (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 11537-11542
    • Cuevas-Ramos, G.1    Petit, C.R.2    Marcq, I.3    Boury, M.4    Oswald, E.5    Nougayrède, J.6
  • 6
    • 84874007506 scopus 로고    scopus 로고
    • High prevalence of mucosa-associated E. Coli producing cyclomodulin and genotoxin in colon cancer
    • Buc, E., Dubois, P., Sauvanet, J., Raisch, J., Delmas, J., Darfeuille-Michaud, A., Pezet, D., and Bonnet, R. (2013) High prevalence of mucosa-associated E. coli producing cyclomodulin and genotoxin in colon cancer PLoS One 8, e56964 10.1371/journal.pone.0056964
    • (2013) PLoS One , vol.8 , pp. e56964
    • Buc, E.1    Dubois, P.2    Sauvanet, J.3    Raisch, J.4    Delmas, J.5    Darfeuille-Michaud, A.6    Pezet, D.7    Bonnet, R.8
  • 7
    • 84879093875 scopus 로고    scopus 로고
    • Screening metatranscriptomes for toxin genes as functional drivers of human colorectal cancer
    • Dutilh, B. E., Backus, L., van Hijum, S. A. F. T., and Tjalsma, H. (2013) Screening metatranscriptomes for toxin genes as functional drivers of human colorectal cancer Best Pract. Res. Clin. Gastroenterol. 27, 85-99 10.1016/j.bpg.2013.03.008
    • (2013) Best Pract. Res. Clin. Gastroenterol. , vol.27 , pp. 85-99
    • Dutilh, B.E.1    Backus, L.2    Van Hijum, S.A.F.T.3    Tjalsma, H.4
  • 9
    • 84874909872 scopus 로고    scopus 로고
    • A prodrug resistance mechanism is involved in colibactin biosynthesis and cytotoxicity
    • Brotherton, C. A. and Balskus, E. P. (2013) A prodrug resistance mechanism is involved in colibactin biosynthesis and cytotoxicity J. Am. Chem. Soc. 135, 3359-3362 10.1021/ja312154m
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 3359-3362
    • Brotherton, C.A.1    Balskus, E.P.2
  • 10
    • 84903719462 scopus 로고    scopus 로고
    • Comparative metabolomics and structural characterizations illuminate colibactin pathway-dependent small molecules
    • Vizcaino, M. I., Engel, P., Trautman, E., and Crawford, J. M. (2014) Comparative metabolomics and structural characterizations illuminate colibactin pathway-dependent small molecules J. Am. Chem. Soc. 136, 9244-9247 10.1021/ja503450q
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 9244-9247
    • Vizcaino, M.I.1    Engel, P.2    Trautman, E.3    Crawford, J.M.4
  • 11
    • 84928549042 scopus 로고    scopus 로고
    • The colibactin warhead crosslinks DNA
    • Vizcaino, M. I. and Crawford, J. M. (2015) The colibactin warhead crosslinks DNA Nat. Chem. 7, 411-417 10.1038/nchem.2221
    • (2015) Nat. Chem. , vol.7 , pp. 411-417
    • Vizcaino, M.I.1    Crawford, J.M.2
  • 12
    • 84925372827 scopus 로고    scopus 로고
    • Isolation of a metabolite from the pks island provides insights into colibactin biosynthesis and activity
    • Brotherton, C. A., Wilson, M., Byrd, G., and Balskus, E. P. (2015) Isolation of a metabolite from the pks island provides insights into colibactin biosynthesis and activity Org. Lett. 17, 1545-1548 10.1021/acs.orglett.5b00432
    • (2015) Org. Lett. , vol.17 , pp. 1545-1548
    • Brotherton, C.A.1    Wilson, M.2    Byrd, G.3    Balskus, E.P.4
  • 13
    • 84928150480 scopus 로고    scopus 로고
    • Two more pieces of the colibactin genotoxin puzzle from Escherichia coli show incorporation of an unusual 1-aminocyclopropanecarboxylic acid moiety
    • Bian, X., Plaza, A., Zhang, R., and Müller, R. (2015) Two more pieces of the colibactin genotoxin puzzle from Escherichia coli show incorporation of an unusual 1-aminocyclopropanecarboxylic acid moiety Chem. Sci. 6, 3154-3160 10.1039/C5SC00101C
    • (2015) Chem. Sci. , vol.6 , pp. 3154-3160
    • Bian, X.1    Plaza, A.2    Zhang, R.3    Müller, R.4
  • 14
    • 84938741118 scopus 로고    scopus 로고
    • Critical intermediates reveal new biosynthetic events in the enigmatic colibactin pathway
    • Li, Z.-R., Li, Y., Lai, J. Y. H., Tang, J., Wang, B., Lu, L., Zhu, G., Wu, X., Xu, Y., and Qian, P.-Y. (2015) Critical intermediates reveal new biosynthetic events in the enigmatic colibactin pathway ChemBioChem 16, 1715-1719 10.1002/cbic.201500239
    • (2015) ChemBioChem , vol.16 , pp. 1715-1719
    • Li, Z.-R.1    Li, Y.2    Lai, J.Y.H.3    Tang, J.4    Wang, B.5    Lu, L.6    Zhu, G.7    Wu, X.8    Xu, Y.9    Qian, P.-Y.10
  • 15
    • 74249120351 scopus 로고    scopus 로고
    • Chemical and biological explorations of the family of CC-1065 and the duocarmycin natural products
    • Ghosh, N., Sheldrake, H. M., Searcey, M., and Pors, K. (2009) Chemical and biological explorations of the family of CC-1065 and the duocarmycin natural products Curr. Top. Med. Chem. 9, 1494-1524 10.2174/156802609789909812
    • (2009) Curr. Top. Med. Chem. , vol.9 , pp. 1494-1524
    • Ghosh, N.1    Sheldrake, H.M.2    Searcey, M.3    Pors, K.4
  • 16
    • 84862271006 scopus 로고    scopus 로고
    • Chemistry and biology of acylfulvenes: Sesquiterpene-derived antitumor agents
    • Tanasova, M. and Sturla, S. J. (2012) Chemistry and biology of acylfulvenes: sesquiterpene-derived antitumor agents Chem. Rev. 112, 3578-3610 10.1021/cr2001367
    • (2012) Chem. Rev. , vol.112 , pp. 3578-3610
    • Tanasova, M.1    Sturla, S.J.2
  • 17
    • 33749249749 scopus 로고    scopus 로고
    • Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type i polyketide synthase extender units
    • Chan, Y. A., Boyne, M. T., Podevels, A. M., Klimowicz, A. K., Handelsman, J., Kelleher, N. L., and Thomas, M. G. (2006) Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units Proc. Natl. Acad. Sci. U. S. A. 103, 14349-14354 10.1073/pnas.0603748103
    • (2006) Proc. Natl. Acad. Sci. U. S. A. , vol.103 , pp. 14349-14354
    • Chan, Y.A.1    Boyne, M.T.2    Podevels, A.M.3    Klimowicz, A.K.4    Handelsman, J.5    Kelleher, N.L.6    Thomas, M.G.7
  • 18
    • 59949101152 scopus 로고    scopus 로고
    • Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus
    • Kevany, B. M., Rasko, D. A., and Thomas, M. G. (2009) Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus Appl. Environ. Microbiol. 75, 1144-1155 10.1128/AEM.02518-08
    • (2009) Appl. Environ. Microbiol. , vol.75 , pp. 1144-1155
    • Kevany, B.M.1    Rasko, D.A.2    Thomas, M.G.3
  • 19
    • 77951685700 scopus 로고    scopus 로고
    • Recognition of (2S)-aminomalonyl-acyl carrier protein (ACP) and (2R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis
    • Chan, Y. A. and Thomas, M. G. (2010) Recognition of (2S)-aminomalonyl-acyl carrier protein (ACP) and (2R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis Biochemistry 49, 3667-3677 10.1021/bi100141n
    • (2010) Biochemistry , vol.49 , pp. 3667-3677
    • Chan, Y.A.1    Thomas, M.G.2
  • 21
    • 84938866475 scopus 로고    scopus 로고
    • Colibactin biosynthesis and biological activity depend on the rare aminomalonyl polyketide precursor
    • Brachmann, A. O., Garcie, C., Wu, V., Martin, P., Ueoka, R., Oswald, E., and Piel, J. (2015) Colibactin biosynthesis and biological activity depend on the rare aminomalonyl polyketide precursor Chem. Commun. 51, 13138-13141 10.1039/C5CC02718G
    • (2015) Chem. Commun. , vol.51 , pp. 13138-13141
    • Brachmann, A.O.1    Garcie, C.2    Wu, V.3    Martin, P.4    Ueoka, R.5    Oswald, E.6    Piel, J.7
  • 22
    • 69249202590 scopus 로고    scopus 로고
    • The biosynthetic logic of polyketide diversity
    • Hertweck, C. (2009) The biosynthetic logic of polyketide diversity Angew. Chem., Int. Ed. 48, 4688-4716 10.1002/anie.200806121
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4688-4716
    • Hertweck, C.1
  • 23
    • 33748631825 scopus 로고    scopus 로고
    • Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: Logic, machinery, and mechanisms
    • Fischbach, M. A. and Walsh, C. T. (2006) Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: logic, machinery, and mechanisms Chem. Rev. 106, 3468-3496 10.1021/cr0503097
    • (2006) Chem. Rev. , vol.106 , pp. 3468-3496
    • Fischbach, M.A.1    Walsh, C.T.2
  • 24
    • 77954675603 scopus 로고    scopus 로고
    • Biosynthesis of polyketides by trans-AT polyketide synthases
    • Piel, J. (2010) Biosynthesis of polyketides by trans-AT polyketide synthases Nat. Prod. Rep. 27, 996-1047 10.1039/b816430b
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 996-1047
    • Piel, J.1
  • 25
    • 84864348214 scopus 로고    scopus 로고
    • Discrete acyltransferases involved in polyketide biosynthesis
    • Musiol, E. M. and Weber, T. (2012) Discrete acyltransferases involved in polyketide biosynthesis MedChemComm 3, 871-886 10.1039/c2md20048a
    • (2012) MedChemComm , vol.3 , pp. 871-886
    • Musiol, E.M.1    Weber, T.2
  • 26
    • 79957511827 scopus 로고    scopus 로고
    • Enacyloxins are products of an unusual hybrid modular polyketide synthase encoded by a cryptic Burkholderia ambifaria genomic island
    • Mahenthiralingam, E., Song, L., Sass, A., White, J., Wilmot, C., Marchbank, A., Boaisha, O., Paine, J., Knight, D., and Challis, G. L. (2011) Enacyloxins are products of an unusual hybrid modular polyketide synthase encoded by a cryptic Burkholderia ambifaria genomic island Chem. Biol. 18, 665-677 10.1016/j.chembiol.2011.01.020
    • (2011) Chem. Biol. , vol.18 , pp. 665-677
    • Mahenthiralingam, E.1    Song, L.2    Sass, A.3    White, J.4    Wilmot, C.5    Marchbank, A.6    Boaisha, O.7    Paine, J.8    Knight, D.9    Challis, G.L.10
  • 27
    • 84922023867 scopus 로고    scopus 로고
    • Gut symbionts from distinct hosts exhibit genotoxic activity via divergent colibactin biosynthesis pathways
    • Engel, P., Vizcaino, M. I., and Crawford, J. M. (2015) Gut symbionts from distinct hosts exhibit genotoxic activity via divergent colibactin biosynthesis pathways Appl. Environ. Microbiol. 81, 1502-1512 10.1128/AEM.03283-14
    • (2015) Appl. Environ. Microbiol. , vol.81 , pp. 1502-1512
    • Engel, P.1    Vizcaino, M.I.2    Crawford, J.M.3
  • 28
    • 77953799129 scopus 로고    scopus 로고
    • Oxazolomycin biosynthesis in Streptomyces albus JA3453 featuring an acyltransferase-less type i polyketide synthase that incorporates two distinct extender units
    • Zhao, C., Coughlin, J. M., Ju, J., Zhu, D., Wendt-Pienkowski, E., Zhou, X., Wang, Z., Shen, B., and Deng, Z. (2010) Oxazolomycin biosynthesis in Streptomyces albus JA3453 featuring an acyltransferase-less type I polyketide synthase that incorporates two distinct extender units J. Biol. Chem. 285, 20097-20108 10.1074/jbc.M109.090092
    • (2010) J. Biol. Chem. , vol.285 , pp. 20097-20108
    • Zhao, C.1    Coughlin, J.M.2    Ju, J.3    Zhu, D.4    Wendt-Pienkowski, E.5    Zhou, X.6    Wang, Z.7    Shen, B.8    Deng, Z.9
  • 30
    • 0032501971 scopus 로고    scopus 로고
    • Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases
    • Quadri, L. E., Weinreb, P. H., Lei, M., Nakano, M. M., Zuber, P., and Walsh, C. T. (1998) Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases Biochemistry 37, 1585-1595 10.1021/bi9719861
    • (1998) Biochemistry , vol.37 , pp. 1585-1595
    • Quadri, L.E.1    Weinreb, P.H.2    Lei, M.3    Nakano, M.M.4    Zuber, P.5    Walsh, C.T.6
  • 31
    • 0024065387 scopus 로고
    • Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12
    • Takamura, Y. and Nomura, G. (1988) Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12 Microbiology 134, 2249-2253 10.1099/00221287-134-8-2249
    • (1988) Microbiology , vol.134 , pp. 2249-2253
    • Takamura, Y.1    Nomura, G.2
  • 32
    • 1542320193 scopus 로고    scopus 로고
    • Manipulation of carrier proteins in antibiotic biosynthesis
    • La Clair, J. J., Foley, T. L., Schegg, T. R., Regan, C. M., and Burkart, M. D. (2004) Manipulation of carrier proteins in antibiotic biosynthesis Chem. Biol. 11, 195-201 10.1016/S1074-5521(04)00032-8
    • (2004) Chem. Biol. , vol.11 , pp. 195-201
    • La Clair, J.J.1    Foley, T.L.2    Schegg, T.R.3    Regan, C.M.4    Burkart, M.D.5
  • 33
    • 0031931702 scopus 로고    scopus 로고
    • Catalytic self-acylation of type II polyketide synthase acyl carrier proteins
    • Hitchman, T. S., Crosby, J., Byrom, K. J., Cox, R. J., and Simpson, T. J. (1998) Catalytic self-acylation of type II polyketide synthase acyl carrier proteins Chem. Biol. 5, 35-47 10.1016/S1074-5521(98)90085-0
    • (1998) Chem. Biol. , vol.5 , pp. 35-47
    • Hitchman, T.S.1    Crosby, J.2    Byrom, K.J.3    Cox, R.J.4    Simpson, T.J.5
  • 36
    • 64049088221 scopus 로고    scopus 로고
    • The DEBS paradigm for type i modular polyketide synthases and beyond
    • Katz, L. (2009) The DEBS paradigm for type I modular polyketide synthases and beyond Methods Enzymol. 459, 113-143 10.1016/S0076-6879(09)04606-0
    • (2009) Methods Enzymol. , vol.459 , pp. 113-143
    • Katz, L.1
  • 37
    • 84902584388 scopus 로고    scopus 로고
    • Comparative analysis of the substrate specificity of trans- versus cis-acyltransferases of assembly line polyketide synthases
    • Dunn, B. J., Watts, K. R., Robbins, T., Cane, D. E., and Khosla, C. (2014) Comparative analysis of the substrate specificity of trans- versus cis-acyltransferases of assembly line polyketide synthases Biochemistry 53, 3796-3806 10.1021/bi5004316
    • (2014) Biochemistry , vol.53 , pp. 3796-3806
    • Dunn, B.J.1    Watts, K.R.2    Robbins, T.3    Cane, D.E.4    Khosla, C.5
  • 38
    • 13444257678 scopus 로고    scopus 로고
    • Bleomycins: Towards better therapeutics
    • Chen, J. and Stubbe, J. (2005) Bleomycins: towards better therapeutics Nat. Rev. Cancer 5, 102-112 10.1038/nrc1547
    • (2005) Nat. Rev. Cancer , vol.5 , pp. 102-112
    • Chen, J.1    Stubbe, J.2
  • 39
    • 0022432366 scopus 로고
    • Is the bithiazole moiety of bleomycin a classical intercalator?
    • Hénichart, J. P., Bernier, J. L., Helbecque, N., and Houssin, R. (1985) Is the bithiazole moiety of bleomycin a classical intercalator? Nucleic Acids Res. 13, 6703-6717 10.1093/nar/13.18.6703
    • (1985) Nucleic Acids Res. , vol.13 , pp. 6703-6717
    • Hénichart, J.P.1    Bernier, J.L.2    Helbecque, N.3    Houssin, R.4
  • 40
    • 0037123195 scopus 로고    scopus 로고
    • Alteration of the selectivity of DNA cleavage by a deglycobleomycin analogue containing a trithiazole moiety
    • Thomas, C. J., McCormick, M. M., Vialas, C., Tao, Z.-F., Leitheiser, C. J., Rishel, M. J., Wu, X., and Hecht, S. M. (2002) Alteration of the selectivity of DNA cleavage by a deglycobleomycin analogue containing a trithiazole moiety J. Am. Chem. Soc. 124, 3875-22901 10.1021/ja011820u
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3875-22901
    • Thomas, C.J.1    McCormick, M.M.2    Vialas, C.3    Tao, Z.-F.4    Leitheiser, C.J.5    Rishel, M.J.6    Wu, X.7    Hecht, S.M.8
  • 41
    • 79953240352 scopus 로고    scopus 로고
    • Comparative analysis of the biosynthetic gene clusters and pathways for three structurally related antitumor antibiotics: Bleomycin, tallysomycin, and zorbamycin
    • Galm, U., Wendt-Pienkowski, E., Wang, L., Huang, S., Unsin, C., Tao, M., Coughlin, J. M., and Shen, B. (2011) Comparative analysis of the biosynthetic gene clusters and pathways for three structurally related antitumor antibiotics: bleomycin, tallysomycin, and zorbamycin J. Nat. Prod. 74, 526-536 10.1021/np1008152
    • (2011) J. Nat. Prod. , vol.74 , pp. 526-536
    • Galm, U.1    Wendt-Pienkowski, E.2    Wang, L.3    Huang, S.4    Unsin, C.5    Tao, M.6    Coughlin, J.M.7    Shen, B.8
  • 42
    • 34047179419 scopus 로고    scopus 로고
    • Bithiazole metabolites from the myxobacterium Myxococcus fulvus
    • Ahn, J. W., Jang, K. H., Yang, H. C., Oh, K. B., Lee, H. S., and Shin, J. (2007) Bithiazole metabolites from the myxobacterium Myxococcus fulvus Chem. Pharm. Bull. 55, 477-479 10.1248/cpb.55.477
    • (2007) Chem. Pharm. Bull. , vol.55 , pp. 477-479
    • Ahn, J.W.1    Jang, K.H.2    Yang, H.C.3    Oh, K.B.4    Lee, H.S.5    Shin, J.6
  • 43
    • 0018372022 scopus 로고
    • Binding of Bleomycin to DNA: Intercalation of bithiazole rings
    • Povirk, L. F., Hogan, M., and Dattagupta, N. (1979) Binding of Bleomycin to DNA: Intercalation of bithiazole rings Biochemistry 18, 96-101 10.1021/bi00568a015
    • (1979) Biochemistry , vol.18 , pp. 96-101
    • Povirk, L.F.1    Hogan, M.2    Dattagupta, N.3
  • 44
    • 58149095417 scopus 로고    scopus 로고
    • Biosynthesis of polyketide synthase extender units
    • Chan, Y. A., Podevels, A. M., Kevany, B. M., and Thomas, M. G. (2009) Biosynthesis of polyketide synthase extender units Nat. Prod. Rep. 26, 90-114 10.1039/B801658P
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 90-114
    • Chan, Y.A.1    Podevels, A.M.2    Kevany, B.M.3    Thomas, M.G.4


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