메뉴 건너뛰기




Volumn 17, Issue 5, 2010, Pages 495-503

Insights into bacterial 6-methylsalicylic acid synthase and its engineering to orsellinic acid synthase for spirotetronate generation

Author keywords

[No Author keywords available]

Indexed keywords

6 METHYLSALICYLIC ACID; 6 METHYLSALICYLIC ACID SYNTHETASE; 6-METHYLSALICYLIC ACID; 6-METHYLSALICYLIC ACID SYNTHETASE; ACYLTRANSFERASE; AMINOGLYCOSIDE; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; CHLOROTHRICIN; LIGASE; MULTIENZYME COMPLEX; ORSELLINIC ACID; OXIDOREDUCTASE; RESORCINOL DERIVATIVE; SALICYLIC ACID DERIVATIVE;

EID: 77954203515     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2010.04.009     Document Type: Article
Times cited : (33)

References (46)
  • 2
    • 0029872079 scopus 로고    scopus 로고
    • Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: Analysis of the enzymatic domains in the modular polyketide synthase
    • DOI 10.1016/0378-1119(95)00800-4
    • J.F. Aparicio, I. Molnar, T. Schwecke, A. Konig, S.F. Haydock, L.E. Khaw, J. Staunton, and P.F. Leadlay Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of the enzymatic domains in the modular polyketide synthase Gene 169 1996 9 16 (Pubitemid 26076611)
    • (1996) Gene , vol.169 , Issue.1 , pp. 9-16
    • Aparicio, J.F.1    Molnar, I.2    Schwecke, T.3    Konig, A.4    Haydock, S.F.5    Khaw, L.E.6    Staunton, J.7    Leadlay, P.F.8
  • 3
    • 34250369120 scopus 로고    scopus 로고
    • Covalent CouN7 enzyme intermediate for acyl group shuttling in aminocoumarin biosynthesis
    • C.J. Balibar, S. Garneau-Tsodikova, and C.T. Walsh Covalent CouN7 enzyme intermediate for acyl group shuttling in aminocoumarin biosynthesis Chem. Biol. 14 2007 679 690
    • (2007) Chem. Biol. , vol.14 , pp. 679-690
    • Balibar, C.J.1    Garneau-Tsodikova, S.2    Walsh, C.T.3
  • 4
    • 0025152833 scopus 로고
    • The multifunctional 6-methylsalicylic acid synthase gene of Penicillium patulum: Its gene structure relative to that of other polyketide synthases
    • J. Beck, S. Ripka, A. Siegner, E. Schiltz, and E. Schweizer The multifunctional 6-methylsalicylic acid synthase gene of Penicillium patulum: its gene structure relative to that of other polyketide synthases Eur. J. Biochem. 192 1990 487 498
    • (1990) Eur. J. Biochem. , vol.192 , pp. 487-498
    • Beck, J.1    Ripka, S.2    Siegner, A.3    Schiltz, E.4    Schweizer, E.5
  • 5
    • 0029161160 scopus 로고
    • Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2)
    • D.J. Bedford, E. Schweizer, D.A. Hopwood, and C. Khosla Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2) J. Bacteriol. 177 1995 4544 4548
    • (1995) J. Bacteriol. , vol.177 , pp. 4544-4548
    • Bedford, D.J.1    Schweizer, E.2    Hopwood, D.A.3    Khosla, C.4
  • 6
    • 0042307438 scopus 로고    scopus 로고
    • Conserved amino acid residues correlating with ketoreductase stereospecificity in modular polyketide synthases
    • P. Caffrey Conserved amino acid residues correlating with ketoreductase stereospecificity in modular polyketide synthases ChemBioChem 4 2003 654 657
    • (2003) ChemBioChem , vol.4 , pp. 654-657
    • Caffrey, P.1
  • 7
    • 0025166586 scopus 로고
    • Site-directed mutagenesis of glycine-14 and two "critical" cysteinyl residues in Drosophila alcohol dehydrogenase
    • Z. Chen, L. Lu, M. Shirley, W.R. Lee, and S.H. Chang Site-directed mutagenesis of glycine-14 and two "critical" cysteinyl residues in Drosophila alcohol dehydrogenase Biochemistry 29 1990 1112 1118
    • (1990) Biochemistry , vol.29 , pp. 1112-1118
    • Chen, Z.1    Lu, L.2    Shirley, M.3    Lee, W.R.4    Chang, S.H.5
  • 10
    • 65549137958 scopus 로고    scopus 로고
    • Organisation of the biosynthetic gene cluster and tailoring enzymes in the biosynthesis of the tetracyclic quinone glycoside antibiotic polyketomycin
    • M. Daum, I. Peintner, A. Linnenbrink, A. Frerich, M. Weber, T. Paululat, and A. Bechthold Organisation of the biosynthetic gene cluster and tailoring enzymes in the biosynthesis of the tetracyclic quinone glycoside antibiotic polyketomycin ChemBioChem 10 2009 1073 1083
    • (2009) ChemBioChem , vol.10 , pp. 1073-1083
    • Daum, M.1    Peintner, I.2    Linnenbrink, A.3    Frerich, A.4    Weber, M.5    Paululat, T.6    Bechthold, A.7
  • 11
    • 0017148183 scopus 로고
    • 6-methylsalicylic acid synthetase from Penicillium patulum. Some catalytic properties of the enzyme and its relation to fatty acid synthetase
    • P. Dimroth, E. Ringelmann, and F. Lynen 6-methylsalicylic acid synthetase from Penicillium patulum. Some catalytic properties of the enzyme and its relation to fatty acid synthetase Eur. J. Biochem. 68 1976 591 596
    • (1976) Eur. J. Biochem. , vol.68 , pp. 591-596
    • Dimroth, P.1    Ringelmann, E.2    Lynen, F.3
  • 12
    • 33746068735 scopus 로고    scopus 로고
    • Acyl transfer in chlorobiocin biosynthesis: Involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar
    • A. Freitag, E. Wemakor, S. Li, and L. Heide Acyl transfer in chlorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar ChemBioChem 6 2005 2316 2325
    • (2005) ChemBioChem , vol.6 , pp. 2316-2325
    • Freitag, A.1    Wemakor, E.2    Li, S.3    Heide, L.4
  • 13
  • 14
    • 0000251771 scopus 로고    scopus 로고
    • Polyketide biosynthesis in filamentous fungi
    • I. Fujii Polyketide biosynthesis in filamentous fungi U. Sankawa, Comprehensive Natural Products Chemistry Volume 1 1999 Elsevier Oxford 409 441
    • (1999) Comprehensive Natural Products Chemistry , vol.1 , pp. 409-441
    • Fujii, I.1
  • 15
    • 0029857563 scopus 로고    scopus 로고
    • Cloning of the polyketide synthase gene atX from Aspergillus terreus and its identification as the 6-methylsalicylic acid synthase gene by heterologous expression
    • I. Fujii, Y. Ono, H. Tada, K. Gomi, Y. Ebizuka, and U. Sankawa Cloning of the polyketide synthase gene atX from Aspergillus terreus and its identification as the 6-methylsalicylic acid synthase gene by heterologous expression Mol. Gen. Genet. 253 1996 1 10
    • (1996) Mol. Gen. Genet. , vol.253 , pp. 1-10
    • Fujii, I.1    Ono, Y.2    Tada, H.3    Gomi, K.4    Ebizuka, Y.5    Sankawa, U.6
  • 16
    • 0030744904 scopus 로고    scopus 로고
    • Cloning of an avilamycin biosynthetic gene cluster from Streptomyces viridochromogenes Tü57
    • S. Gaisser, A. Trefzer, S. Stockert, A. Kirschning, and A. Bechthold Cloning of an avilamycin biosynthetic gene cluster from Streptomyces viridochromogenes Tü57 J. Bacteriol. 179 1997 6271 6278
    • (1997) J. Bacteriol. , vol.179 , pp. 6271-6278
    • Gaisser, S.1    Trefzer, A.2    Stockert, S.3    Kirschning, A.4    Bechthold, A.5
  • 17
    • 65549091812 scopus 로고    scopus 로고
    • Dissection of two acyl-transfer reactions centered on acyl-S-carrier protein intermediates for incorporating 5-chloro-6-methyl-O-methylsalicyclic acid into chlorothricin
    • Q. He, X. Jia, M. Tang, Z. Tian, G. Tang, and W. Liu Dissection of two acyl-transfer reactions centered on acyl-S-carrier protein intermediates for incorporating 5-chloro-6-methyl-O-methylsalicyclic acid into chlorothricin ChemBioChem 10 2009 813 819
    • (2009) ChemBioChem , vol.10 , pp. 813-819
    • He, Q.1    Jia, X.2    Tang, M.3    Tian, Z.4    Tang, G.5    Liu, W.6
  • 18
    • 64049097106 scopus 로고    scopus 로고
    • Aminocoumarins mutasynthesis, chemoenzymatic synthesis, and metabolic engineering
    • L. Heide Aminocoumarins mutasynthesis, chemoenzymatic synthesis, and metabolic engineering Methods Enzymol. 459 2009 437 455
    • (2009) Methods Enzymol. , vol.459 , pp. 437-455
    • Heide, L.1
  • 19
    • 69249202590 scopus 로고    scopus 로고
    • The biosynthetic logic of polyketide diversity
    • C. Hertweck The biosynthetic logic of polyketide diversity Angew. Chem. Int. Ed. Engl. 48 2009 4688 4716
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , pp. 4688-4716
    • Hertweck, C.1
  • 21
    • 33745184421 scopus 로고    scopus 로고
    • Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis
    • X. Jia, Z. Tian, L. Shao, X. Qu, Q. Zhao, J. Tang, G. Tang, and W. Liu Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis Chem. Biol. 13 2006 575 585
    • (2006) Chem. Biol. , vol.13 , pp. 575-585
    • Jia, X.1    Tian, Z.2    Shao, L.3    Qu, X.4    Zhao, Q.5    Tang, J.6    Tang, G.7    Liu, W.8
  • 22
    • 0026529387 scopus 로고
    • New cholesterol biosynthesis inhibitors MC-031 (O-demethylchlorothricin), -032 (O-demethylhydroxychlorothricin), -033 and -034
    • A. Kawashima, Y. Nakamura, Y. Ohta, T. Akama, M. Yamagishi, and K. Hanada New cholesterol biosynthesis inhibitors MC-031 (O-demethylchlorothricin), -032 (O-demethylhydroxychlorothricin), -033 and -034 J. Antibiot. (Tokyo) 45 1992 207 212
    • (1992) J. Antibiot. (Tokyo) , vol.45 , pp. 207-212
    • Kawashima, A.1    Nakamura, Y.2    Ohta, Y.3    Akama, T.4    Yamagishi, M.5    Hanada, K.6
  • 23
    • 0031905709 scopus 로고    scopus 로고
    • Production of a polyketide natural product in nonpolyketide producing prokaryotic and eukaryotic hosts
    • J.T. Kealey, L. Liu, D.V. Santi, M.C. Betlach, and P.J. Barr Production of a polyketide natural product in nonpolyketide producing prokaryotic and eukaryotic hosts Proc. Natl. Acad. Sci. USA 95 1998 505 509
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 505-509
    • Kealey, J.T.1    Liu, L.2    Santi, D.V.3    Betlach, M.C.4    Barr, P.J.5
  • 24
    • 34547945950 scopus 로고    scopus 로고
    • A tylosin ketoreductase reveals how chirality is determined in polyketides
    • A.T. Keatinge-Clay A tylosin ketoreductase reveals how chirality is determined in polyketides Chem. Biol. 14 2007 898 908
    • (2007) Chem. Biol. , vol.14 , pp. 898-908
    • Keatinge-Clay, A.T.1
  • 25
    • 84980128776 scopus 로고
    • Metabolic products of microorganisms. Chlorothricin and deschlorothricin
    • W. Keller-Schierlein, R. Muntwyler, W. Pache, and H. Zähner Metabolic products of microorganisms. Chlorothricin and deschlorothricin Helv. Chim. Acta 52 1969 127 142
    • (1969) Helv. Chim. Acta , vol.52 , pp. 127-142
    • Keller-Schierlein, W.1    Muntwyler, R.2    Pache, W.3    Zähner, H.4
  • 26
    • 0033591447 scopus 로고    scopus 로고
    • Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis
    • J. Kennedy, K. Auclair, S.G. Kendrew, C. Park, J.C. Vederas, and C.R. Hutchinson Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis Science 284 1999 1368 1372
    • (1999) Science , vol.284 , pp. 1368-1372
    • Kennedy, J.1    Auclair, K.2    Kendrew, S.G.3    Park, C.4    Vederas, J.C.5    Hutchinson, C.R.6
  • 29
    • 14844353677 scopus 로고    scopus 로고
    • Genetic approaches to polyketide antibiotics. 1
    • R. McDaniel, M. Welch, and C.R. Hutchinson Genetic approaches to polyketide antibiotics. 1 Chem. Rev. 105 2005 543 558
    • (2005) Chem. Rev. , vol.105 , pp. 543-558
    • McDaniel, R.1    Welch, M.2    Hutchinson, C.R.3
  • 30
    • 33845422572 scopus 로고    scopus 로고
    • Analysis of subunit interactions in the iterative type i polyketide synthase ATX from Aspergillus terreus
    • T. Moriguchi, Y. Ebizuka, and I. Fujii Analysis of subunit interactions in the iterative type I polyketide synthase ATX from Aspergillus terreus ChemBioChem 7 2006 1869 1874
    • (2006) ChemBioChem , vol.7 , pp. 1869-1874
    • Moriguchi, T.1    Ebizuka, Y.2    Fujii, I.3
  • 31
    • 49249094525 scopus 로고    scopus 로고
    • Domain-domain interactions in the iterative type i polyketide synthase ATX from Aspergillus terreus
    • T. Moriguchi, Y. Ebizuka, and I. Fujii Domain-domain interactions in the iterative type I polyketide synthase ATX from Aspergillus terreus ChemBioChem 9 2008 1207 1212
    • (2008) ChemBioChem , vol.9 , pp. 1207-1212
    • Moriguchi, T.1    Ebizuka, Y.2    Fujii, I.3
  • 34
    • 0028356539 scopus 로고
    • Structure of the NADPH-binding motif of glutathione reductase: Efficiency determined by evolution
    • M. Rescigno, and R.N. Perham Structure of the NADPH-binding motif of glutathione reductase: efficiency determined by evolution Biochemistry 33 1994 5721 5727
    • (1994) Biochemistry , vol.33 , pp. 5721-5727
    • Rescigno, M.1    Perham, R.N.2
  • 35
    • 0033107932 scopus 로고    scopus 로고
    • Tolerance and specificity of recombinant 6-methylsalicylic acid synthase
    • M.T. Richardson, N.L. Pohl, J.T. Kealey, and C. Khosla Tolerance and specificity of recombinant 6-methylsalicylic acid synthase Metab. Eng. 1 1999 180 187
    • (1999) Metab. Eng. , vol.1 , pp. 180-187
    • Richardson, M.T.1    Pohl, N.L.2    Kealey, J.T.3    Khosla, C.4
  • 37
    • 0015278552 scopus 로고
    • Metabolic products of microorganisms. 96. Mechanism of action of the macrolide-type antibiotic, chlorothricin. I. Inhibitor of the pyruvate carboxylase from Bacillus subtilis
    • P.W. Schindler, and H. Zähner Metabolic products of microorganisms. 96. Mechanism of action of the macrolide-type antibiotic, chlorothricin. I. Inhibitor of the pyruvate carboxylase from Bacillus subtilis Arch. Mikrobiol. 82 1972 66 75
    • (1972) Arch. Mikrobiol. , vol.82 , pp. 66-75
    • Schindler, P.W.1    Zähner, H.2
  • 38
    • 33646397902 scopus 로고    scopus 로고
    • Cloning and characterization of a bacterial iterative type i polyketide synthase gene encoding the 6-methylsalicyclic acid synthase
    • L. Shao, X. Qu, X. Jia, Q. Zhao, Z. Tian, M. Wang, G. Tang, and W. Liu Cloning and characterization of a bacterial iterative type I polyketide synthase gene encoding the 6-methylsalicyclic acid synthase Biochem. Biophys. Res. Commun. 345 2006 133 139
    • (2006) Biochem. Biophys. Res. Commun. , vol.345 , pp. 133-139
    • Shao, L.1    Qu, X.2    Jia, X.3    Zhao, Q.4    Tian, Z.5    Wang, M.6    Tang, G.7    Liu, W.8
  • 39
    • 0000427346 scopus 로고    scopus 로고
    • Biosynthesis of aromatic polyketides
    • B. Shen Biosynthesis of aromatic polyketides Top. Curr. Chem. 209 2000 1 51
    • (2000) Top. Curr. Chem. , vol.209 , pp. 1-51
    • Shen, B.1
  • 40
    • 33846312155 scopus 로고    scopus 로고
    • Characterization of SyrC, an aminoacyltransferase shuttling threonyl and chlorothreonyl residues in the syringomycin biosynthetic assembly line
    • G.M. Singh, F.H. Vaillancourt, J. Yin, and C.T. Walsh Characterization of SyrC, an aminoacyltransferase shuttling threonyl and chlorothreonyl residues in the syringomycin biosynthetic assembly line Chem. Biol. 14 2007 31 40
    • (2007) Chem. Biol. , vol.14 , pp. 31-40
    • Singh, G.M.1    Vaillancourt, F.H.2    Yin, J.3    Walsh, C.T.4
  • 41
    • 0027054628 scopus 로고
    • Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum
    • J.B. Spencer, and P.M. Jordan Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum Biochem. J. 288 1992 839 846
    • (1992) Biochem. J. , vol.288 , pp. 839-846
    • Spencer, J.B.1    Jordan, P.M.2
  • 43
    • 23944436899 scopus 로고    scopus 로고
    • Biosynthesis of the β-amino acid moiety of the enediyne antitumor antibiotic C-1027 featuring β-amino acyl-S-carrier protein intermediates
    • S.G. Van Lanen, P.C. Dorrestein, S.D. Christenson, W. Liu, J. Ju, N.L. Kelleher, and B. Shen Biosynthesis of the β-amino acid moiety of the enediyne antitumor antibiotic C-1027 featuring β-amino acyl-S-carrier protein intermediates J. Am. Chem. Soc. 127 2005 11594 11595
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 11594-11595
    • Van Lanen, S.G.1    Dorrestein, P.C.2    Christenson, S.D.3    Liu, W.4    Ju, J.5    Kelleher, N.L.6    Shen, B.7
  • 44
    • 35848971002 scopus 로고    scopus 로고
    • Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis
    • S.G. Van Lanen, T.-J. Oh, W. Liu, E. Wendt-Pienkowski, and B. Shen Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis J. Am. Chem. Soc. 129 2007 13082 13094
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 13082-13094
    • Van Lanen, S.G.1    Oh, T.-J.2    Liu, W.3    Wendt-Pienkowski, E.4    Shen, B.5
  • 45
    • 29044437969 scopus 로고    scopus 로고
    • Polyketide double bond biosynthesis. Mechanistic analysis of the dehydratase-containing module 2 of the picromycin/methymycin polyketide synthase
    • J. Wu, T.J. Zaleski, C. Valenzano, C. Khosla, and D.E. Cane Polyketide double bond biosynthesis. Mechanistic analysis of the dehydratase-containing module 2 of the picromycin/methymycin polyketide synthase J. Am. Chem. Soc. 127 2005 17393 17404
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 17393-17404
    • Wu, J.1    Zaleski, T.J.2    Valenzano, C.3    Khosla, C.4    Cane, D.E.5
  • 46
    • 46849109297 scopus 로고    scopus 로고
    • Characterization of the azinomycin B biosynthetic gene cluster revealing a different iterative type i polyketide synthase for naphthoate biosynthesis
    • Q. Zhao, Q. He, W. Ding, M. Tang, Q. Kang, Y. Yu, W. Deng, Q. Zhang, J. Fang, G. Tang, and W. Liu Characterization of the azinomycin B biosynthetic gene cluster revealing a different iterative type I polyketide synthase for naphthoate biosynthesis Chem. Biol. 15 2008 693 705
    • (2008) Chem. Biol. , vol.15 , pp. 693-705
    • Zhao, Q.1    He, Q.2    Ding, W.3    Tang, M.4    Kang, Q.5    Yu, Y.6    Deng, W.7    Zhang, Q.8    Fang, J.9    Tang, G.10    Liu, W.11


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.