Biosynthesis of ubiquinone compounds with conjugated prenyl side chains

Applied and Environmental Microbiology

Volumn 74, Issue 22, 2008, Pages 6908-6917

  Pyung, Cheon Lee ^a,b   Salomon, Christine ^a   Mijts, Benjamin ^a,c   Schmidt Dannert, Claudia ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b Ajou University   (South Korea)

^c R and D Project Development and Management   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; BIOMATERIALS; BIOSYNTHESIS; COENZYMES; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAGNETIC RESONANCE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; RESONANCE; WATER POLLUTION;

ANTIOXIDANT PROPERTIES; BIOSYNTHESIS PATHWAYS; BIOSYNTHETIC PATHWAYS; CONJUGATED DOUBLE BONDS; DESATURASE; DESATURATION; DIPHOSPHATES; E. COLI; IN VITRO; IN VITRO ACTIVITIES; IN-VIVO; INHERENT FLEXIBILITIES; MODEL SYSTEMS; NEW CLASSES; NEW STRUCTURES; SIDE CHAINS; STAPHYLOCOCCUS AUREUS; STRUCTURAL MOTIFS; SUBSTRATE RECOGNITIONS; SYNTHESIS OF; UBIQUINONE;

PLANTS (BOTANY);

BETA CAROTENE; CARBON 14; CAROTENOID; LINOLEIC ACID; PRENYLAMINE; TRITIUM; UBIQUINONE;

ANTIOXIDANT; BACTERIUM; COMPARATIVE STUDY; ENZYME ACTIVITY; MASS SPECTROMETRY;

ANTIOXIDANT ACTIVITY; ARTICLE; BACTERIAL GROWTH; BIOSYNTHESIS; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MASS SPECTROMETRY; METABOLITE; MOLECULAR CLONING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESPIRATORY CHAIN; STAPHYLOCOCCUS AUREUS;

BACTERIAL PROTEINS; ESCHERICHIA COLI; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METABOLIC NETWORKS AND PATHWAYS; MOLECULAR STRUCTURE; NEOPRENE; OXIDOREDUCTASES; STAPHYLOCOCCUS AUREUS; UBIQUINONE;

ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS;

EID: 55949095380     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.01495-08     Document Type: Article

References (53)

1. Britton, G., S. Liaaen-Jensen, and H. Pfander. 1995. Carotenoids: spectroscopy, vol. 1B. Birkhauser, Basel, Switzerland.
2. Brown, K. R., B. M. Allan, P. Do, and E. L. Hegg. 2002. Identification of novel hemes generated by heme A synthase: evidence for two successive monooxygenase reactions. Biochemistry 41:10906-10913.
3. Burda, S., and W. Oleszek. 2001. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 49:2774-2779.
4. Cluis, C. P., A. M. Burja, and V. J. Martin. 2007. Current prospects for the production of coenzyme Q10 in microbes. Trends Biotechnol. 25:514-521.
5. Copley, S. D. 2000. Evolution of a metabolic pathway for degradation of a toxic xenobiotic: the patchwork approach. Trends Biochem. Sci. 25:261-265.
6. Cox, G. B., I. G. Young, L. M. McCann, and F. Gibson. 1969. Biosynthesis of ubiquinone in Escherichia coli K-12: location of genes affecting the metabolism of 3-octaprenyl-4-hydroxybenzoic acid and 2-octaprenylphenol. J. Bacteriol. 99:450-458.
7. 10. J. Am. Coll. Nutr. 20:591-598.
8. Enzell, C. R., G. W. Francis, and S. Liaaen-Jensen. 1969. Mass spectrometric studies of carotenoids. 2. A survey of fragmentation reactions. Acta Chem. Scand. 23:727-750.
9. Facchini, P. J. 2001. Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52:29-66.
10. Firn, R. D., and C. G. Jones. 2003. Natural products - a simple model to explain chemical diversity. Nat. Prod. Rep. 20:382-391.
11. Fujisaki, S., T. Nishino, and H. Katsuki. 1986. Biosynthesis of isoprenoids in intact cells of Escherichia coli. J. Biochem. (Tokyo) 99:1137-1146.
12. Hauss, T., S. Dante, T. H. Haines, and N. A. Dencher. 2005. Localization of coenzyme Q10 in the center of a deuterated lipid membrane by neutron diffraction. Biochim. Biophys. Acta 1710:57-62.
13. Hemmi, H., Y. Takahashi, K. Shibuya, T. Nakayama, and T. Nishino. 2005. Menaquinone-specific prenyl reductase from the hyperthermophilic archaeon Archaeoglobus fulgidus. J. Bacteriol. 187:1937-1944.
14. Kainou, T., K. Okada, K. Suzuki, T. Nakagawa, H. Matsuda, and M. Kawamukai. 2001. Dimer formation of octaprenyl-diphosphate synthase (IspB) is essential for chain length determination of ubiquinone. J. Biol. Chem. 276:7876-7883.
15. Kuzuyama, T., J. P. Noel, and S. B. Richard. 2005. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435:983-987.
16. Lee, P. C., B. N. Mijts, R. Petri, K. T. Watts, and C. Schmidt-Dannert. 2004. Alteration of product specificity of Aeropyrum pernix farnesylgeranyl diphosphate synthase (Fgs) by directed evolution. Prot. Eng. Des. Sel. 17:771-777.
17. Lee, P. C., A. Z. Momen, B. N. Mijts, and C. Schmidt-Dannert. 2003. Biosynthesis of structurally novel carotenoids in Escherichia coli. Chem. Biol. 10:453-462.
18. Lee, P. C., R. Petri, B. N. Mijts, K. T. Watts, and C. Schmidt-Dannert. 2005. Directed evolution of Escherichia coli farnesyl diphosphate synthase (IspA) reveals novel structural determinants of chain length specificity. Metab. Eng. 7:18-26.
19. Lee, P. C., and C. Schmidt-Dannert. 2002. Metabolic engineering towards biotechnological production of carotenoids in microorganisms. Appl. Microbiol. Biotechnol. 60:1-11.
20. Lee, P. T., A. Y. Hsu, H. T. Ha, and C. F. Clarke. 1997. A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene. J. Bacteriol. 179:1748-1754.
21. Lenaz, G. 1985. Coenzyme Q: biochemistry, bioenergetics and clinical applications of ubiquinone. John Wiley & Sons, New York, NY.
22. Meganathan, R. 2001. Ubiquinone biosynthesis in microorganisms. FEMS Microbiol. Lett. 203:131-139.
23. Melzer, M., and L. Heide. 1994. Characterization of polyprenyldiphosphate: 4-hydroxybenzoate polyprenyltransferase from Escherichia coli. Biochim. Biophys. Acta 1212:93-102.
24. Mijts, B. N., P. C. Lee, and C. Schmidt-Dannert. 2005. Identification of a carotenoid oxygenase synthesizing acyclic xanthophylls: combinatorial biosynthesis and directed evolution. Chem. Biol. 12:453-460.
25. Mijts, B. N., and C. Schmidt-Dannert. 2003. Engineering of secondary metabolite pathways. Curr. Opin. Biotechnol. 14:597-602.
26. Motchnik, P. A., B. Frei, and B. N. Ames. 1994. Measurement of antioxidants in human blood plasma. Methods Enzymol. 234:269-279.
27. Mukai, K., A. Tokunaga, S. Itoh, Y. Kanesaki, K. Ohara, S. Nagaoka, and K. Abe. 2007. Structure-activity relationship of the free-radical-scavenging reaction by vitamin E (alpha-, beta-, gamma-, delta-tocopherols) and ubiquinol-10: pH dependence of the reaction rates. J. Phys. Chem. B 111:652-662.
28. Müller, M. 2004. Chemical diversity through biotransformations. Curr. Opin. Biotechnol. 15:591-598.
29. Okada, K., Y. Kamiya, X. Zhu, K. Suzuki, K. Tanaka, T. Nakagawa, H. Matsuda, and M. Kawamukai. 1997. Cloning of the sdsA gene encoding solanesyl diphosphate synthase from Rhodobacter capsulatus and its functional expression in Escherichia coli and Saccharomyces cerevisiae. J. Bacteriol. 179:5992-5998.
30. Petri, R., and C. Schmidt-Dannert. 2004. Dealing with complexity: evolutionary engineering and genome shuffling. Curr. Opin. Biotechnol. 15:298-304.
31. Raisig, A., and G. Sandmann. 1999. 4,4′-diapophytoene desaturase: catalytic properties of an enzyme from the C-30 carotenoid pathway of Staphylococcus aureus. J. Bacteriol. 181:6184-6187.
32. Raisig, A., and G. Sandmann. 2001. Functional properties of diapophytoene and related desaturases of C-30 and C-40 carotenoid biosynthetic pathways. Biochim. Biophys. Acta 1533:164-170.
33. Schmidt-Dannert, C. 2001. Directed evolution of single proteins, metabolic pathways and viruses. Biochemistry 40:13125-13136.
34. Schmidt-Dannert, C., D. Umeno, and F. H. Arnold. 2000. Molecular breeding of carotenoid biosynthetic pathways. Nat. Biotechnol. 18:750-753.
35. Schneider, C., P. Boger, and G. Sandmann. 1997. Phytoene desaturase: heterologous expression in an active state, purification, and biochemical properties. Prot. Expr. Purif. 10:175-179.
36. 10 by recombinant E. coli harboring the decaprenyl diphosphate synthase gene from Sinorhizobium meliloti. J. Microbiol. Biotechnol. 16:933-938.
37. Soballe, B., and R. K. Poole. 1999. Microbial ubiquinones: multiple roles in respiration, gene regulation and oxidative stress management. Microbiology 145:1817-1830.
38. Soballe, B., and R. K. Poole. 1998. Requirement for ubiquinone downstream of cytochrome(s) b in the oxygen-terminated respiratory chains of Escherichia coli K-12 revealed using a null mutant allele of ubiCA. Microbiology 144:361-373.
39. Soballe, B., and R. K. Poole. 2000. Ubiquinone limits oxidative stress in Escherichia coli. Microbiology 146:787-796.
40. Tran, U. C., and C. F. Clarke. 2007. Endogenous synthesis of coenzyme Q in eukaryotes. Mitochondrion 7(Suppl.):S62-S71.
41. Trumpower, B. L., A. S. Aiyar, C. E. Opliger, and R. E. Olson. 1972. Studies on ubiquinone. The isolation and identification of 5-demethoxyubiquinone-9 as an intermediate in biosynthesis of ubiquinone-9 in the rat. J. Biol. Chem. 247:2499-2511.
42. Turunen, M., J. Olsson, and G. Dallner. 2004. Metabolism and function of coenzyme Q. Biochim. Biophys. Acta 1660:171-199.
43. Umeno, D., A. V. Tobias, and F. H. Arnold. 2005. Diversifying carotenoid biosynthetic pathways by directed evolution. Microbiol. Mol. Biol. Rev. 69:51-78.
44. 40 pathway. J. Bacteriol. 184:6690-6699.
45. Valentin, H. E., and Q. Qi. 2005. Biotechnological production and application of vitamin E: current state and prospects. Appl. Microbiol. Biotechnol. 68:436-444.
46. Wallace, B. J., and I. G. Young. 1977. Role of quinones in electron transport to oxygen and nitrate in Escherichia coli. Studies with a ubiA-menA-double quinone mutant. Biochim. Biophys. Acta 461:84-100.
47. Wang, C. W., and J. C. Liao. 2001. Alteration of product specificity of Rhodobacter sphaeroides phytoene desaturase by directed evolution. J. Biol. Chem. 276:41161-41164.
48. Watts, K. T., B. N. Mijts, and C. Schmidt-Dannert. 2005. Current and emerging approaches for natural product biosynthesis in microbial cells. Adv. Synth. Catal. 347:927-940.
49. Willows, R. D. 2003. Biosynthesis of chlorophylls from protoporphyrin IX. Nat. Prod. Rep. 20:327-341.
50. Wissenbach, U., D. Ternes, and G. Unden. 1992. An Escherichia coli mutant containing only demethylmenaquinone, but no menaquinone: effects on fumarate, dimethylsulfoxide, trimethylamine N-oxide and nitrate respiration. Arch. Microbiol. 158:68-73.
51. Yazaki, K., M. Kunihisa, T. Fujisaki, and F. Sato. 2002. Geranyl diphosphate: 4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a key enzyme in shikonin biosynthesis. J. Biol. Chem. 277:6240-6246.
52. Zahiri, H. S., S. H. Yoon, J. D. Keasling, S. H. Lee, S. Won Kim, S. C. Yoon, and Y. C. Shin. 2006. Coenzyme Q10 production in recombinant Escherichia coli strains engineered with a heterologous decaprenyl diphosphate synthase gene and foreign mevalonate pathway. Metab. Eng. 8:406-416.
53. Zhang, D. W., B. Shrestha, Z. P. Li, and T. W. Tan. 2007. Ubiquinone-10 production using Agrobacterium tumefaciens dps gene in Escherichia coli by coexpression system. Mol. Biotechnol. 35:1-14.