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Volumn 20, Issue 7, 2013, Pages 879-887

Tandem enzymatic oxygenations in biosynthesis of epoxyquinone pharmacophore of manumycin-type metabolites

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 4 HYDROXYL BENZOIC ACID; ADENOSINE TRIPHOSPHATE DEPENDENT ADENYLASE; ASUE 1 PROTEIN; ASUE 3 PROTEIN; BENZOIC ACID DERIVATIVE; CARRIER PROTEINS AND BINDING PROTEINS; DRUG METABOLITE; EPOXYQUINONE; MANUMYCIN; QUERCETIN; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

EID: 84880898014     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.05.006     Document Type: Article
Times cited : (5)

References (39)
  • 1
    • 27544432463 scopus 로고    scopus 로고
    • Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases
    • D.P. Ballou, B. Entsch, and L.J. Cole Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases Biochem. Biophys. Res. Commun. 338 2005 590 598
    • (2005) Biochem. Biophys. Res. Commun. , vol.338 , pp. 590-598
    • Ballou, D.P.1    Entsch, B.2    Cole, L.J.3
  • 3
    • 20144385856 scopus 로고    scopus 로고
    • Removal of a methyl group causes global changes in p-hydroxybenzoate hydroxylase
    • L.J. Cole, D.L. Gatti, B. Entsch, and D.P. Ballou Removal of a methyl group causes global changes in p-hydroxybenzoate hydroxylase Biochemistry 44 2005 8047 8058
    • (2005) Biochemistry , vol.44 , pp. 8047-8058
    • Cole, L.J.1    Gatti, D.L.2    Entsch, B.3    Ballou, D.P.4
  • 5
    • 9744270010 scopus 로고    scopus 로고
    • Protein dynamics and electrostatics in the function of p-hydroxybenzoate hydroxylase
    • B. Entsch, L.J. Cole, and D.P. Ballou Protein dynamics and electrostatics in the function of p-hydroxybenzoate hydroxylase Arch. Biochem. Biophys. 433 2005 297 311
    • (2005) Arch. Biochem. Biophys. , vol.433 , pp. 297-311
    • Entsch, B.1    Cole, L.J.2    Ballou, D.P.3
  • 6
    • 38349074340 scopus 로고    scopus 로고
    • Mycobacterial phenolic glycolipid virulence factor biosynthesis: Mechanism and small-molecule inhibition of polyketide chain initiation
    • J.A. Ferreras, K.L. Stirrett, X.Q. Lu, J.S. Ryu, C.E. Soll, D.S. Tan, and L.E.N. Quadri Mycobacterial phenolic glycolipid virulence factor biosynthesis: mechanism and small-molecule inhibition of polyketide chain initiation Chem. Biol. 15 2008 51 61
    • (2008) Chem. Biol. , vol.15 , pp. 51-61
    • Ferreras, J.A.1    Stirrett, K.L.2    Lu, X.Q.3    Ryu, J.S.4    Soll, C.E.5    Tan, D.S.6    Quadri, L.E.N.7
  • 7
    • 69549111337 scopus 로고    scopus 로고
    • Antibiotics for emerging pathogens
    • M.A. Fischbach, and C.T. Walsh Antibiotics for emerging pathogens Science 325 2009 1089 1093
    • (2009) Science , vol.325 , pp. 1089-1093
    • Fischbach, M.A.1    Walsh, C.T.2
  • 10
    • 0004895156 scopus 로고
    • Isolation and characterization of desepoxy-4,5-didehydro-methylenomycin- A, precursor of antibiotic methylenomycin-A in Scp1+ strains of Streptomyces Coelicolor A3(2)
    • U. Hornemann, and D.A. Hopwood Isolation and characterization of desepoxy-4,5-didehydro-methylenomycin-A, precursor of antibiotic methylenomycin-A in Scp1+ strains of Streptomyces Coelicolor A3(2) Tetrahedron Lett. 33 1978 2977 2978
    • (1978) Tetrahedron Lett. , vol.33 , pp. 2977-2978
    • Hornemann, U.1    Hopwood, D.A.2
  • 11
    • 1642333610 scopus 로고    scopus 로고
    • Further studies on the biosynthesis of the manumycin-type antibiotic, asukamycin, and the chemical synthesis of protoasukamycin
    • Y.D. Hu, and H.G. Floss Further studies on the biosynthesis of the manumycin-type antibiotic, asukamycin, and the chemical synthesis of protoasukamycin J. Am. Chem. Soc. 126 2004 3837 3844
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3837-3844
    • Hu, Y.D.1    Floss, H.G.2
  • 12
    • 33947228281 scopus 로고    scopus 로고
    • Starter unit specificity of the asukamycin "upper" chain polyketide synthase and the branched-chain fatty acid synthase of Streptomyces nodosus subsp asukaensis
    • Y.D. Hu, and H.G. Floss Starter unit specificity of the asukamycin "upper" chain polyketide synthase and the branched-chain fatty acid synthase of Streptomyces nodosus subsp asukaensis Heterocycles 69 2006 133 149
    • (2006) Heterocycles , vol.69 , pp. 133-149
    • Hu, Y.D.1    Floss, H.G.2
  • 15
    • 38549124488 scopus 로고    scopus 로고
    • Crystal structure of the flavin reductase component (HpaC) of 4-hydroxyphenylacetate 3-monooxygenase from Thermus thermophilus HB8: Structural basis for the flavin affinity
    • S.H. Kim, T. Hisano, W. Iwasaki, A. Ebihara, and K. Miki Crystal structure of the flavin reductase component (HpaC) of 4-hydroxyphenylacetate 3-monooxygenase from Thermus thermophilus HB8: Structural basis for the flavin affinity Proteins 70 2008 718 730
    • (2008) Proteins , vol.70 , pp. 718-730
    • Kim, S.H.1    Hisano, T.2    Iwasaki, W.3    Ebihara, A.4    Miki, K.5
  • 16
    • 0030448374 scopus 로고    scopus 로고
    • TMC-1 A, B, C and D, new antibiotics of the manumycin group produced by Streptomyces sp. Taxonomy, production, isolation, physico-chemical properties, structure elucidation and biological properties
    • J. Kohno, M. Nishio, K. Kawano, N. Nakanishi, S. Suzuki, T. Uchida, and S. Komatsubara TMC-1 A, B, C and D, new antibiotics of the manumycin group produced by Streptomyces sp. Taxonomy, production, isolation, physico-chemical properties, structure elucidation and biological properties J. Antibiot. 49 1996 1212 1220
    • (1996) J. Antibiot. , vol.49 , pp. 1212-1220
    • Kohno, J.1    Nishio, M.2    Kawano, K.3    Nakanishi, N.4    Suzuki, S.5    Uchida, T.6    Komatsubara, S.7
  • 17
    • 0041529865 scopus 로고    scopus 로고
    • EI-1941-1 and -2, novel interleukin-1 beta converting enzyme inhibitors Produced by Farrowia sp. E-1941. II. Taxonomy of producing strain, fermentation, isolation, physico-chemical properties, and biological properties
    • F. Koizumi, H. Ishiguro, K. Ando, H. Kondo, M. Yoshida, Y. Matsuda, and S. Nakanishi EI-1941-1 and -2, novel interleukin-1 beta converting enzyme inhibitors Produced by Farrowia sp. E-1941. II. Taxonomy of producing strain, fermentation, isolation, physico-chemical properties, and biological properties J. Antibiot. 56 2003 603 609
    • (2003) J. Antibiot. , vol.56 , pp. 603-609
    • Koizumi, F.1    Ishiguro, H.2    Ando, K.3    Kondo, H.4    Yoshida, M.5    Matsuda, Y.6    Nakanishi, S.7
  • 19
    • 30744462550 scopus 로고    scopus 로고
    • Syntheses of natural products having an epoxyquinone structure
    • K. Miyashita, and T. Imanishi Syntheses of natural products having an epoxyquinone structure Chem. Rev. 105 2005 4515 4536
    • (2005) Chem. Rev. , vol.105 , pp. 4515-4536
    • Miyashita, K.1    Imanishi, T.2
  • 20
    • 56349131283 scopus 로고    scopus 로고
    • Aranorosin and a novel derivative inhibit the anti-apoptotic functions regulated by Bcl-2
    • T. Nakashima, R. Tanaka, Y. Yamashita, Y. Kanda, and M. Hara Aranorosin and a novel derivative inhibit the anti-apoptotic functions regulated by Bcl-2 Biochem. Biophys. Res. Commun. 377 2008 1085 1090
    • (2008) Biochem. Biophys. Res. Commun. , vol.377 , pp. 1085-1090
    • Nakashima, T.1    Tanaka, R.2    Yamashita, Y.3    Kanda, Y.4    Hara, M.5
  • 22
    • 0035793858 scopus 로고    scopus 로고
    • Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli
    • B.A. Pfeifer, S.J. Admiraal, H. Gramajo, D.E. Cane, and C. Khosla Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli Science 291 2001 1790 1792
    • (2001) Science , vol.291 , pp. 1790-1792
    • Pfeifer, B.A.1    Admiraal, S.J.2    Gramajo, H.3    Cane, D.E.4    Khosla, C.5
  • 23
    • 0033617184 scopus 로고    scopus 로고
    • Molecular characterization of the genes of actinomycin synthetase i and of a 4-methyl-3-hydroxyanthranilic acid carrier protein involved in the assembly of the acylpeptide chain of actinomycin in Streptomyces
    • F. Pfennig, F. Schauwecker, and U. Keller Molecular characterization of the genes of actinomycin synthetase I and of a 4-methyl-3-hydroxyanthranilic acid carrier protein involved in the assembly of the acylpeptide chain of actinomycin in Streptomyces J. Biol. Chem. 274 1999 12508 12516
    • (1999) J. Biol. Chem. , vol.274 , pp. 12508-12516
    • Pfennig, F.1    Schauwecker, F.2    Keller, U.3
  • 24
    • 80054686056 scopus 로고    scopus 로고
    • Effect of starter unit availability on the spectrum of manumycin-type metabolites produced by Streptomyces nodosus ssp. asukaensis
    • S. Pospíšil, K. Petříčková, P. Sedmera, P. Halada, J. Olšovská, and M. Petří ček Effect of starter unit availability on the spectrum of manumycin-type metabolites produced by Streptomyces nodosus ssp. asukaensis J. Appl. Microbiol. 111 2011 1116 1128
    • (2011) J. Appl. Microbiol. , vol.111 , pp. 1116-1128
    • Pospíšil, S.1    Petříčková, K.2    Sedmera, P.3    Halada, P.4    Olšovská, J.5    Petříček, M.6
  • 25
    • 0031923560 scopus 로고    scopus 로고
    • Cloning and physical mapping of the EcoRI fragments of the giant linear plasmid SCP1
    • M. Redenbach, K. Ikeda, M. Yamasaki, and H. Kinashi Cloning and physical mapping of the EcoRI fragments of the giant linear plasmid SCP1 J. Bacteriol. 180 1998 2796 2799
    • (1998) J. Bacteriol. , vol.180 , pp. 2796-2799
    • Redenbach, M.1    Ikeda, K.2    Yamasaki, M.3    Kinashi, H.4
  • 27
    • 84871585975 scopus 로고    scopus 로고
    • Enzymatic synthesis of dilactone scaffold of antimycins
    • M. Sandy, Z. Rui, J. Gallagher, and W. Zhang Enzymatic synthesis of dilactone scaffold of antimycins ACS Chem. Biol. 7 2012 1956 1961
    • (2012) ACS Chem. Biol. , vol.7 , pp. 1956-1961
    • Sandy, M.1    Rui, Z.2    Gallagher, J.3    Zhang, W.4
  • 29
    • 0036773256 scopus 로고    scopus 로고
    • Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin-activating enzyme
    • R. Sekizawa, S. Ikeno, H. Nakamura, H. Naganawa, S. Matsui, H. Iinuma, and T. Takeuchi Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin-activating enzyme J. Nat. Prod. 65 2002 1491 1493
    • (2002) J. Nat. Prod. , vol.65 , pp. 1491-1493
    • Sekizawa, R.1    Ikeno, S.2    Nakamura, H.3    Naganawa, H.4    Matsui, S.5    Iinuma, H.6    Takeuchi, T.7
  • 31
    • 34249283081 scopus 로고    scopus 로고
    • Farnesyltransferase inhibitor, manumycin a, prevents atherosclerosis development and reduces oxidative stress in apolipoprotein E-deficient mice
    • M. Sugita, H. Sugita, and M. Kaneki Farnesyltransferase inhibitor, manumycin a, prevents atherosclerosis development and reduces oxidative stress in apolipoprotein E-deficient mice Arterioscler. Thromb. Vasc. Biol. 27 2007 1390 1395
    • (2007) Arterioscler. Thromb. Vasc. Biol. , vol.27 , pp. 1390-1395
    • Sugita, M.1    Sugita, H.2    Kaneki, M.3
  • 32
    • 33846025770 scopus 로고    scopus 로고
    • Novel benzene ring biosynthesis from C(3) and C(4) primary metabolites by two enzymes
    • H. Suzuki, Y. Ohnishi, Y. Furusho, S. Sakuda, and S. Horinouchi Novel benzene ring biosynthesis from C(3) and C(4) primary metabolites by two enzymes J. Biol. Chem. 281 2006 36944 36951
    • (2006) J. Biol. Chem. , vol.281 , pp. 36944-36951
    • Suzuki, H.1    Ohnishi, Y.2    Furusho, Y.3    Sakuda, S.4    Horinouchi, S.5
  • 33
    • 0029857599 scopus 로고    scopus 로고
    • EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. III. Biochemical properties of EI-1511-3, -5 and EI-1625-2
    • T. Tanaka, E. Tsukuda, Y. Uosaki, and Y. Matsuda EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. III. Biochemical properties of EI-1511-3, -5 and EI-1625-2 J. Antibiot. 49 1996 1085 1090
    • (1996) J. Antibiot. , vol.49 , pp. 1085-1090
    • Tanaka, T.1    Tsukuda, E.2    Uosaki, Y.3    Matsuda, Y.4
  • 35
    • 33745991798 scopus 로고    scopus 로고
    • Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts
    • W.J.H. van Berkel, N.M. Kamerbeek, and M.W. Fraaije Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts J. Biotechnol. 124 2006 670 689
    • (2006) J. Biotechnol. , vol.124 , pp. 670-689
    • Van Berkel, W.J.H.1    Kamerbeek, N.M.2    Fraaije, M.W.3
  • 36
    • 0032924489 scopus 로고    scopus 로고
    • Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene
    • M.J. van der Werf, H.J. Swarts, and J.A.M. de Bont Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene Appl. Environ. Microbiol. 65 1999 2092 2102
    • (1999) Appl. Environ. Microbiol. , vol.65 , pp. 2092-2102
    • Van Der Werf, M.J.1    Swarts, H.J.2    De Bont, J.A.M.3
  • 38
    • 76249124150 scopus 로고    scopus 로고
    • Characterization of chlorophenol 4-monooxygenase (TftD) and NADH:FAD oxidoreductase (TftC) of Burkholderia cepacia AC1100
    • B.N. Webb, J.W. Ballinger, E. Kim, S.M. Belchik, K.S. Lam, B. Youn, M.S. Nissen, L.Y. Xun, and C. Kang Characterization of chlorophenol 4-monooxygenase (TftD) and NADH:FAD oxidoreductase (TftC) of Burkholderia cepacia AC1100 J. Biol. Chem. 285 2010 2014 2027
    • (2010) J. Biol. Chem. , vol.285 , pp. 2014-2027
    • Webb, B.N.1    Ballinger, J.W.2    Kim, E.3    Belchik, S.M.4    Lam, K.S.5    Youn, B.6    Nissen, M.S.7    Xun, L.Y.8    Kang, C.9
  • 39
    • 33847726165 scopus 로고    scopus 로고
    • Isolation and characterization of N98-1272 A, B and C, selective acetylcholinesterase inhibitors from metabolites of an actinomycete strain
    • Z.H. Zheng, Y.S. Dong, H. Zhang, X.H. Lu, X. Ren, G.Y. Zhao, J.G. He, and S.Y. Si Isolation and characterization of N98-1272 A, B and C, selective acetylcholinesterase inhibitors from metabolites of an actinomycete strain J. Enzyme Inhib. Med. Chem. 22 2007 43 49
    • (2007) J. Enzyme Inhib. Med. Chem. , vol.22 , pp. 43-49
    • Zheng, Z.H.1    Dong, Y.S.2    Zhang, H.3    Lu, X.H.4    Ren, X.5    Zhao, G.Y.6    He, J.G.7    Si, S.Y.8


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