메뉴 건너뛰기




Volumn 5, Issue 11, 1998, Pages 661-667

Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae

Author keywords

Cytochrome P450; Macrolide antibiotics; Narbomycin; Polyketide synthase; YC 17

Indexed keywords

CARBON; CULTURE MEDIUM; CULTURE TECHNIQUE; CYTOCHROME P450; ENZYME SPECIFICITY; ESCHERICHIA COLI; GENE CLUSTER; HIS TAGGED PROTEIN; HYDROXYLATION; MACROLACTONE; METHYMYCIN; MICROBE METABOLISM; NARBOMYCIN; NEOMETHYMYCIN; PIKROMYCIN; SECONDARY METABOLITE;

EID: 0032213230     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90293-9     Document Type: Article
Times cited : (119)

References (24)
  • 1
    • 0030009067 scopus 로고    scopus 로고
    • Bacterial cytochromes P450
    • Munro, A.W. & Lindsay, J.G. (1996). Bacterial cytochromes P450. Mol. Microbiol. 20, 1115-1125.
    • (1996) Mol. Microbiol. , vol.20 , pp. 1115-1125
    • Munro, A.W.1    Lindsay, J.G.2
  • 2
    • 0025999536 scopus 로고
    • Cloning and sequence analysis of genes involved in erythromycin biosynthesis in Saccharopolyspora erythraea: Sequence similarities between EryG and a family of S-adenosylmethionine-dependent methyltransferases
    • Haydock, S.F., Dowson, J.A., Dhillon, N., Roberts, G.A., Cortes, J. & Leadlay, P.F. (1991). Cloning and sequence analysis of genes involved in erythromycin biosynthesis in Saccharopolyspora erythraea: sequence similarities between EryG and a family of S-adenosylmethionine-dependent methyltransferases. Mol. Gen. Genet. 230, 120-128.
    • (1991) Mol. Gen. Genet. , vol.230 , pp. 120-128
    • Haydock, S.F.1    Dowson, J.A.2    Dhillon, N.3    Roberts, G.A.4    Cortes, J.5    Leadlay, P.F.6
  • 3
    • 0026500150 scopus 로고
    • Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase
    • Andersen, J.F. & Hutchinson, C.R. (1992). Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase. J. Bacteriol. 174, 725-735.
    • (1992) J. Bacteriol. , vol.174 , pp. 725-735
    • Andersen, J.F.1    Hutchinson, C.R.2
  • 4
    • 0027455631 scopus 로고
    • Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis
    • Stassi, D., Donadio, S., Staver, M.J. & Katz, L. (1993). Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis. J. Bacteriol. 175, 182-189.
    • (1993) J. Bacteriol. , vol.175 , pp. 182-189
    • Stassi, D.1    Donadio, S.2    Staver, M.J.3    Katz, L.4
  • 5
    • 0029586252 scopus 로고
    • Structure of cytochrome P450eryF involved in erythromycin biosynthesis
    • Cupp-Vickery, J.R. & Poulos, T.L. (1995). Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Nat. Struct. Biol. 2, 144-153.
    • (1995) Nat. Struct. Biol. , vol.2 , pp. 144-153
    • Cupp-Vickery, J.R.1    Poulos, T.L.2
  • 6
    • 0029883934 scopus 로고    scopus 로고
    • Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: Analysis of genes flanking the polyketide synthase
    • Molnar, I., et al., & Leadlay, P.F. (1996). Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase. Gene 169, 1-7.
    • (1996) Gene , vol.169 , pp. 1-7
    • Molnar, I.1    Leadlay, P.F.2
  • 7
    • 0029098323 scopus 로고
    • The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin
    • Schwecke, T., et al. & Leadlay, P.F. (1995). The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl Acad. Sci. USA 92, 7839-7843.
    • (1995) Proc. Natl Acad. Sci. USA , vol.92 , pp. 7839-7843
    • Schwecke, T.1    Leadlay, P.F.2
  • 8
    • 0028072875 scopus 로고
    • Characterization and expression of a P-450-like mycinamicin biosynthesis gene using a novel Micromonospora-Escherichia coll shuttle cosmid vector
    • Inouye, M., Takada, Y., Muto, N., Beppu, T. & Horinouchi, S. (1994). Characterization and expression of a P-450-like mycinamicin biosynthesis gene using a novel Micromonospora-Escherichia coll shuttle cosmid vector. Mol. Gen. Genet. 245, 456-64.
    • (1994) Mol. Gen. Genet. , vol.245 , pp. 456-464
    • Inouye, M.1    Takada, Y.2    Muto, N.3    Beppu, T.4    Horinouchi, S.5
  • 9
    • 0032565060 scopus 로고    scopus 로고
    • Methymycin biosynthesis: Isolation of P450 monooxygenase activity in a cell-free system from Streptomyces venezuelae
    • Cane, D.E. & Graziani, E.I. (1998). Methymycin biosynthesis: isolation of P450 monooxygenase activity in a cell-free system from Streptomyces venezuelae. J. Am. Chem. Soc. 120, 2682-2683.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2682-2683
    • Cane, D.E.1    Graziani, E.I.2
  • 10
    • 0032514668 scopus 로고    scopus 로고
    • A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: Architecture of metabolic diversity
    • Xue, Y., Zhao, L., Liu, H.-w. & Sherman, D.H. (1998). A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc. Natl Acad. Sci. USA. 95, 12111-12116.
    • (1998) Proc. Natl Acad. Sci. USA , vol.95 , pp. 12111-12116
    • Xue, Y.1    Zhao, L.2    Liu, H.-W.3    Sherman, D.H.4
  • 11
    • 0027512258 scopus 로고
    • Substrate specificity of 6-deoxyerythronolide B hydroxylase, a bacterial cytochrome P450 of erythromycin A biosynthesis
    • Andersen, J.F., Tatsuta, K., Gunji, H., Ishiyama, T. & Hutchinson, C.R. (1993). Substrate specificity of 6-deoxyerythronolide B hydroxylase, a bacterial cytochrome P450 of erythromycin A biosynthesis. Biochemistry 32, 1905-1913.
    • (1993) Biochemistry , vol.32 , pp. 1905-1913
    • Andersen, J.F.1    Tatsuta, K.2    Gunji, H.3    Ishiyama, T.4    Hutchinson, C.R.5
  • 12
    • 85007823413 scopus 로고
    • Nucleotide sequence analysis of the carbomycin biosynthetic genes including the 3-O-acyltransferase gene from Streptomyces thermotolerans
    • Arisawa, A., Tsunekawa, H., Okamura, K. & Okamoto, R. (1995). Nucleotide sequence analysis of the carbomycin biosynthetic genes including the 3-O-acyltransferase gene from Streptomyces thermotolerans. Biosci. Biotechnol. Biochem. 59, 582-588.
    • (1995) Biosci. Biotechnol. Biochem. , vol.59 , pp. 582-588
    • Arisawa, A.1    Tsunekawa, H.2    Okamura, K.3    Okamoto, R.4
  • 13
    • 0028910531 scopus 로고
    • A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis by Streptomyces antibioticus
    • Rodriguez, A.M., Olano, C., Mendez, C., Hutchinson, C.R. & Salas, J.A. (1995). A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis by Streptomyces antibioticus. FEMS Microbiol. Lett. 127, 117-120.
    • (1995) FEMS Microbiol. Lett. , vol.127 , pp. 117-120
    • Rodriguez, A.M.1    Olano, C.2    Mendez, C.3    Hutchinson, C.R.4    Salas, J.A.5
  • 14
    • 0030729349 scopus 로고    scopus 로고
    • A second type I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC29253, a rapamycin-producing strain
    • Ruan, X., Stassi, D., Lax, S. & Katz, L. (1997). A second type I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC29253, a rapamycin-producing strain. Gene 203, 1-9.
    • (1997) Gene , vol.203 , pp. 1-9
    • Ruan, X.1    Stassi, D.2    Lax, S.3    Katz, L.4
  • 15
    • 0027520649 scopus 로고
    • Nucleotide sequence analysis of a region upstream of the cholesterol oxidase-oytochrome P450 operon of Streptomyces sp. SA-COO revealing repeating units coding for putative transmembrane and DNA-binding proteins
    • Molner, I. & Murooka, Y. (1993). Nucleotide sequence analysis of a region upstream of the cholesterol oxidase-oytochrome P450 operon of Streptomyces sp. SA-COO revealing repeating units coding for putative transmembrane and DNA-binding proteins. J. Ferment. Bioeng. 76, 257-263.
    • (1993) J. Ferment. Bioeng. , vol.76 , pp. 257-263
    • Molner, I.1    Murooka, Y.2
  • 16
    • 9444271749 scopus 로고    scopus 로고
    • Biosynthesis of 3-amino-5-hydroxybenzoic acid, the precursor of mC7N unit in ansamycin antibiotics
    • Kim, C.-G., et al., & Floss, H.G. (1996). Biosynthesis of 3-amino-5-hydroxybenzoic acid, the precursor of mC7N unit in ansamycin antibiotics. J. Am. Chem. Soc. 118, 7486-7491.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7486-7491
    • Kim, C.-G.1    Floss, H.G.2
  • 17
    • 0028142101 scopus 로고
    • Dual interacting two-component regulatory systems mediate nitrate- and nitrite-regulated gene expression in Escherichia coli
    • Stewart, V. (1994). Dual interacting two-component regulatory systems mediate nitrate- and nitrite-regulated gene expression in Escherichia coli. Res. Microbiol. 145, 450-454.
    • (1994) Res. Microbiol. , vol.145 , pp. 450-454
    • Stewart, V.1
  • 18
    • 0028928086 scopus 로고
    • Overproduction and characterization of the erythromycin C-12 hydroxylase, EryK
    • Lambalot, R.H., Cane, D.E., Aparicio, J.J. & Katz, L. (1995). Overproduction and characterization of the erythromycin C-12 hydroxylase, EryK. Biochemistry 34, 1858-66.
    • (1995) Biochemistry , vol.34 , pp. 1858-1866
    • Lambalot, R.H.1    Cane, D.E.2    Aparicio, J.J.3    Katz, L.4
  • 19
    • 0032541989 scopus 로고    scopus 로고
    • Macrolide biosynthesis: A single cytochrome P450, PickC, is responsible for the hydroxylations that generate methymycin, neomethymycin, and pikromycin in Streptomyces venezuelae
    • in press
    • Graziani, E.I, Cane, D.E., Detlach, M.C., Kealey, J.T. & McDaniel, R. (1998). Macrolide biosynthesis: a single cytochrome P450, PickC, is responsible for the hydroxylations that generate methymycin, neomethymycin, and pikromycin in Streptomyces venezuelae. Bioorg. Med. Chem. Lett., in press.
    • (1998) Bioorg. Med. Chem. Lett.
    • Graziani, E.I.1    Cane, D.E.2    Detlach, M.C.3    Kealey, J.T.4    McDaniel, R.5
  • 21
    • 0027105048 scopus 로고
    • Isolation and characterization of 10-deoxymethynolide produced by Streptomyces venezuelae
    • Lambalot, R.H. & Cane, D.E. (1992). Isolation and characterization of 10-deoxymethynolide produced by Streptomyces venezuelae. J. Antibiot. 45, 1981-1982.
    • (1992) J. Antibiot. , vol.45 , pp. 1981-1982
    • Lambalot, R.H.1    Cane, D.E.2
  • 22
    • 0015944636 scopus 로고
    • Isolation and identification of picronolide, methynolide and neomethynolide produced by Streptomyces venezuelae MCRL-0376
    • Maezawa, L., Kinnmaki, A. & Suzuki, M. (1974). Isolation and identification of picronolide, methynolide and neomethynolide produced by Streptomyces venezuelae MCRL-0376. J. Antibiot. 27, 84-85.
    • (1974) J. Antibiot. , vol.27 , pp. 84-85
    • Maezawa, L.1    Kinnmaki, A.2    Suzuki, M.3
  • 23
    • 0026645203 scopus 로고
    • Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli toStreptomyces spp
    • Bierman, M., Logan, R., O'Brien, K., Seno, E.T., Nagaraja Rao, R. & Schoner, B.E. (1992). Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli toStreptomyces spp. Gene 116, 43-49.
    • (1992) Gene , vol.116 , pp. 43-49
    • Bierman, M.1    Logan, R.2    O'Brien, K.3    Seno, E.T.4    Nagaraja Rao, R.5    Schoner, B.E.6
  • 24
    • 0027509115 scopus 로고
    • Macrolide biosynthesis 7. Incorporation of polyketide chain elongation intermediates into methymycin
    • Cane D.E., Lambalot R.H., Prabhakaran P.C. & Ott W.R. (1993). Macrolide biosynthesis 7. Incorporation of polyketide chain elongation intermediates into methymycin. J. Am. Chem. Soc. 115, 522-526.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 522-526
    • Cane, D.E.1    Lambalot, R.H.2    Prabhakaran, P.C.3    Ott, W.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.