생명과학회지 (Journal of Life Science)

  • 제12권5호
  • /
  • Pages.632-648
  • /
  • 2002
  • /
  • 1225-9918(pISSN)
  • /
  • 2287-3406(eISSN)
한국생명과학회 (Korean Society of Life Science)
권호 표지
DOI QR코드

DOI QR Code

Polyketide 이차대사물질의 생합성

Biosynthesis of Polyketide Secondary Metabolites

  • 윤여준 (울산대학교 공과대학 생명화학공학부) ;
  • 송재경 (선문대학교 자연과학부, 생체분자재설계연구소)
  • 발행 : 2002.10.01
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

The term polyketide defines a class of natural products synthesized through the successive condensation of small arboxylic acids, which results in products containing multiple carbonyl or hydroxyl groups, each separated by one arbon atom, as in the structural element CH$_2$C(=0)CH$_2$CH(OE)CH$_2$C(=0)-. Plant flavonoids, fungal aflatoxins, as well as undreds of compounds of different structures that can inhibit the growth of bacteria, viruses, fungi, parasites or human umor cells are included in this diverse group. Some of antifungal polyketides also have immunosuppresive activity. olyketides can vary widely in structure, and the diversity of polyketide structures reflects the wide variety of their iological properties. This review focuses on the biosynthesis of polyketides and recent progress in combinatorial iosynthesis of new hybrid polyketide compounds.

키워드

참고문헌

  1. Chem, Biol. v.5 Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699 August, P.R.;L. Tang;Y. J. Yoon;S. Ning;R. Mueller;T. W. Yu;M. Taylor;D. Hoffmann;C. G. Kim;X. Zhang;C. R. Hutchinson;H. G. Floss https://doi.org/10.1016/S1074-5521(98)90141-7
  2. Eur. J. Biochem. v.192 The multifunctional 6-methylsalicylic acid synthase gene of Penicillium patulum.Its gene structure relative to that of other polyketide synthases Beck, J.;S. Ripka;A. Siegner;E. Schiltz;E. Schweizer https://doi.org/10.1111/j.1432-1033.1990.tb19252.x
  3. J. Bacteriol v.177 Expression of a functional fungal polyketide synthase in the bacterium Streptomyces coelicolor A3(2) Bedford, D. J.;E. Schweizer;D. A. Hopwood;C. Khosla https://doi.org/10.1128/jb.177.15.4544-4548.1995
  4. Gene v.142 Cloning, sequencing and deduced functions of a cluster of Streptomyces genes probably encoding biosynthesis of the polyketide antibiotic frenolicin Bibb, M. J.; D. H. Sherman;S. Omura;D.A. Hopwood https://doi.org/10.1016/0378-1119(94)90351-4
  5. EMBO J. v.8 Analysis of the nucleotide sequence of the Streptomyces glaucescens tcmⅠ genes provides key information about the enzymology of polyketide antibiotic biosynthesis Bibb, M. J.;S. Biro;H. Motamedi;J. F. Collins;C. R. Hutchinson
  6. Proc. Natl. Acad. Sci. USA. v.97 Deoxysugars in glycopeptide antibiotics: enzymatic synthesis of TDP-L-epivancosamine in chloroeremomycin biosynthesis Chen, H.;M. G. Thomas;B. K. Hubbard;H. C. Losey;C. T. Walsh;M. D. Burkart https://doi.org/10.1073/pnas.210395097
  7. J. Antibiot. v.40 Biosynthesis of the antibiotic actinorhodin. Analysis of blocked mutants of Streptomyces coelicolor Cole, S. P.;B. A. M. Rudd;D. A. Hopwood;C. J.Chang;H. G. Floss https://doi.org/10.7164/antibiotics.40.340
  8. Nature v.348 An unusually large multifunctional polypeptide in the erythromycin-producing polyketide synthase of Saccharospolyspora erythraea Cortes, J.;S. F. Haydock;G. A. Roberts;D. J. Bevitt;P. F. Leadlay https://doi.org/10.1038/348176a0
  9. Eur. J. Biochem. v.13 Biosynthesis of 6-methylsalicylic acid Dimroth, P.;H. Walter;F. Lynen https://doi.org/10.1111/j.1432-1033.1970.tb00904.x
  10. Gene v.111 Organization of the enzymatic domains in the mutifuctional polyketide synthase involved in erythromycin formation in Saccharopolyspora erythraea Donadio, S.;L. Katz https://doi.org/10.1016/0378-1119(92)90602-L
  11. Science v.252 Modular organization of the genes required for complex polyketide biosynthesis Donadio, S.;M. J. Staver;J. B. McAlpine;S. J. Swanson;L. Katz https://doi.org/10.1126/science.2024119
  12. Chem. Biol. v.4 Engineered biosynthesis of novel polyketides: evidence for temporal, but not regiospecific, control of cyclization of an aromatic polyketide precurson Fu, H.;D. A. Hopwood;C. Khosla
  13. Gene v.74 Nucleotide sequence, transcription and deduced function of a gene involved in polyketide antibiotic synthesis in Streptomyces coelicolor Hallam, S. E.;F. Malpartida;D. A. Hopwood https://doi.org/10.1016/0378-1119(88)90165-5
  14. Microbiology v.140 Cloning and characterization of polyketide synthase genes for jadomycin B biosynthesis in Streptomyces venezuelae ISP5230 Han, L.;K. Yang;E. Ramalingam;R. H. Mosher;L. C. Vining https://doi.org/10.1099/13500872-140-12-3379
  15. J. Bacteriol. v.179 Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis Kakavas, S. J.;L. Katz;D. Stassi
  16. J. Am. Chem. Soc. v.116 Engineered biosynthesis of triketide lactone from an incomplete modular polyketide synthase Kao, C. M.;G. Luo;L. Katz;D. E. Cane;C. Khosla https://doi.org/10.1021/ja00104a069
  17. Science v.265 Engineered biosynthesis of a complete macrolactone in a heterologous host Kao, C. M.;L. Katz;C. Khosla https://doi.org/10.1126/science.8036492
  18. J. Am. Chem. Soc. v.117 Manipulation of macrolide ring size by directed mutagenesis of a modular polyketide synthase Kao, C.M.;Luo, G.;Katz, L.;Cane, D. E.;Khosla, C. https://doi.org/10.1021/ja00140a043
  19. Chem. Rev. v.97 Manipulation of modular polyketide synthase Katz, L. https://doi.org/10.1021/cr960025+
  20. Annu. Rev. Microbiol. v.47 Polyketide synthesis: prospects for hybrid antibiotics Katz, L.;S. Donadio. https://doi.org/10.1146/annurev.mi.47.100193.004303
  21. Gene v.141 Sequences of the oxytetracycline polyketide synthase-encoding otc genes from Streptomyces rimosus Kim, E.-S.;M. J. Bibb;M. J. Butler;D. A. Hopwood;D. H. Sherman https://doi.org/10.1073/pnas.95.2.505
  22. J. Am. Chem. Soc. v.119 Rational Design and Engineered Biosynthesis of a Novel 18-Carbon Aromatic Polyketide Kramer, P.J.;J. X. Zawada;R. McDaniel;C. R. Hutchinson;D. A. Hopwood;C. Khosla https://doi.org/10.1016/0378-1119(94)90144-9
  23. Proc. Natl. Acad. Sci. USA. v.95 Production of a polyketide natural product in nonpolyketide-producing prokaryotic and eukaryotic hosts Kealey, J.T.;L. Liu;D. V. Santi;M. C. Betlach;P. J. Barr https://doi.org/10.1021/ja962888q
  24. Gene v.172 Characterization of Streptomyces argillaceus genes encoding a polyketide synthase involved in the biosynthesis of the antitumor mithramycin Lombo, F.;G. Blanco;E. Fernandez;C. Mendez;J. A. Salas https://doi.org/10.1016/0378-1119(96)00029-7
  25. Ann. N. Y. Acad. Sci. v.721 Correlation of the avermectin polyketide synthase genes to the avermectin structure. Implications for designing novel avermectins MacNeil, D. J.;J. L. Occi;K. M. Gewain;T. MacNeil https://doi.org/10.1111/j.1749-6632.1994.tb47384.x
  26. Nature v.309 Molecular cloning of the whole biosynthetic pathway of a Streptomyces antibiotic and its expression in a heterologous host Malpartida, F.;D.A. Hopwood https://doi.org/10.1038/309462a0
  27. J. Am. Chem. Soc. v.119 Gain-of -function mutagenesis of a modular polyketide synthases McDaniel, R.;C. M. Kao;H. Fu;P. Hevezi;C. Gustafsson;M. Betlach;G. Ashley;D. E. Cane;C. Khosla https://doi.org/10.1021/ja9702531
  28. Science v.262 Engineered biosynthesis of novel polyketides McDaniel, R.;S. E. Khosla;D. A. Hopwood;C. Khosla https://doi.org/10.1126/science.8248802
  29. J. Am. Chem. Soc. v.115 Engineered biosynthesis of novel polyketides: manipulation and analysis of an aromatic polyketide synthase with unproven catalytic specificities McDaniel, R.;S. E. Khosla;D. A. Hopwood;C. Khosla https://doi.org/10.1021/ja00078a002
  30. Nature v.375 Rational design of aromatic polyketide natural products by recombinant assembly of enzymatic subunits McDaniel, R.;S.E. Khosla;D. A. Hopwood;C. Khosla https://doi.org/10.1038/375549a0
  31. Proc. Natl. Acad. Sci. USA. v.91 Engineered biosynthesis of novel polyketides: influence of a downstream enzyme on the catalytic specificity of a minimal aromatic polyketide synthase McDaniel, R.;S.E. Khosla;H. Fu;D. A. Hopwood;C. Khosla https://doi.org/10.1073/pnas.91.24.11542
  32. Mol. Microbiol. v.13 Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome Merson_Davies, L. A.;E. Cundliffe https://doi.org/10.1111/j.1365-2958.1994.tb00428.x
  33. J. Am. Chem. Soc. v.117 Daunorubicin type Ⅱ polyketide synthase enzymes DpsA and DpsB determine neither the choice of starter unit nor the cyclization pattern of aromatic polyketides Meurer, G.;C.R. Hutchinson https://doi.org/10.1021/ja00126a049
  34. Chem. Biol. v.4 Iterative type Ⅱ polyketide synthases, cyclases and ketoreductases exhibit context-dependent behavior in the biosynthesis of linear and angular decapolyketides Meurer, G.;M. Gerlitz;W. Pienkowski;L. C. Vining;J. Rohr;C. R. Hutchinson
  35. The Polyketide Metabolites O'Hagen, D.
  36. J. Am. Chem. Soc. v.117 Remarkably broad substrate specificity of a modular polyketide synthase in a cell-free system Pieper, R.;G. Luo;D. E. Cane;C. Khosla https://doi.org/10.1021/ja00150a049
  37. J. Bacteriol. v.179 Minimal Streptomyces sp. strain C5 daunorubicin polyketide biosynthesis genes required for aklanonic acid biosynthesis Rajgarhia, V. B.;W. R. Strohl https://doi.org/10.1128/jb.179.8.2690-2696.1997
  38. Gene v.203 A second type-ⅠPKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain Ruan, X.;D. Stassi;S. Lax;L. Katz https://doi.org/10.1016/S0378-1119(97)00450-2
  39. J. Am. Chem. Soc. v.117 The Streptomyces glaucescens tcmKL polyketide synthase and tcmN polyketide cyclase genes govern the size and shape of aromatic polyketides Shen, B.;R. G. Summers;W. Pienkowski;C. R. Hutchinson https://doi.org/10.1021/ja00131a002
  40. EMBO J. v.8 Structure and deduced function of the granaticin-producing polykitide synthase gene cluster of Streptomyces violaceoruber Tu22 Sherman, D. H.;F. Malpartida;M. J. Bibb;H. M. Kieser;D. H. Hopwood
  41. Biochem. J. v.288 Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum. Spender, J. B.;P. M. Jordan https://doi.org/10.1042/bj2880839
  42. J. Bacteriol. v.175 The tcmⅥ region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens encodes the tetracenomycin F1 monooxygenase, tetracenomycin F2 cyclase, and, most likely, a second cyclase Summers, R. G.;E. Wendi-Pienkowski;H. Motamedi;C. R. Hutchinson
  43. J. Bacteriol. v.176 Nucleotide sequence of the aknA region of the aklavinone biosynthetic gene cluster of Streptomyces galilaeus Tsukamoto, N. https://doi.org/10.1128/jb.176.8.2473-2475.1994
  44. Proc. Natl. Acad. Sci. USA v.96 A multiplasmid approach to preparing large libraries of polyketides Xue, Q;G. Asley;C. R. Hutchinson;D. V. Sante https://doi.org/10.1073/pnas.96.21.11740
  45. J. Bacteriol v.176 Cloning, sequencing, and analysis of the griseusin polyketide synthase gene cluster from Streptomyces griseus Yu, T.-W.;M. J. Bibb;P. W. Revill;D. A. Hopwood https://doi.org/10.1128/jb.176.9.2627-2634.1994
  46. J. Am. Chem. Soc. v.120 Biosynthesis of desosamine-Construction of a new methymycin/neomethymycin analogue by deletion of a desosamine biosynthetic gene Zhao, L.;D. H. Sherman;H. W. Liu https://doi.org/10.1021/ja981782n