Farnesol production from Escherichia coli by harnessing the exogenous mevalonate pathway

Biotechnology and Bioengineering

Volumn 107, Issue 3, 2010, Pages 421-429

  Wang, Chonglong ^a   Yoon, Sang Hwal ^a   Shah, Asad Ali ^a   Chung, Young Ryun ^a   Kim, Jae Yean ^a   Choi, Eui Sung ^b   Keasling, Jay D ^c   Kim, Seon Won ^a  

^a Gyeongsang National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^c University of California   (United States)

Author keywords

E. coli; Farnesol; FPP synthase; Mevalonate pathway; Phosphatase

Indexed keywords

E. COLI; FARNESOL; MEVALONATE PATHWAY; PHOSPHATASE; SYNTHASES; CULTURE BROTHS; EFFICIENT SYNTHESIS; FARNESYL PYROPHOSPHATES; MEVALONATE; MVA PATHWAYS; OVER-EXPRESSION; RECOMBINANT E. COLI;

COMPENSATION (PERSONNEL); PARAFFINS; PHOSPHATASES;

ESCHERICHIA COLI;

DIMETHYLALLYLTRANSFERASE; FARNESOL; FARNESYL DIPHOSPHATE; ISOPENTENYL DIPHOSPHATE; MEVALONIC ACID; SYNTHETASE; DECANE; GENOMIC DNA;

ARTICLE; BACTERIUM CULTURE; BIOSYNTHESIS; BROTH DILUTION; CONTROLLED STUDY; CULTURE TECHNIQUE; DEPHOSPHORYLATION; DRUG SYNTHESIS; ESCHERICHIA COLI; GENE OVEREXPRESSION; METABOLIC ENGINEERING; NONHUMAN; PLASMID; BACTERIAL STRAIN; DEPYROPHOSPHORYLATION; EXTRACTION; PHOSPHORYLATION; PROTEIN SYNTHESIS;

CULTURE MEDIA; ESCHERICHIA COLI; FARNESOL; GENE DOSAGE; GENE EXPRESSION; GERANYLTRANSTRANSFERASE; HEMITERPENES; METABOLIC NETWORKS AND PATHWAYS; MEVALONIC ACID; ORGANOPHOSPHORUS COMPOUNDS; PLASMIDS; POLYISOPRENYL PHOSPHATES; SESQUITERPENES;

ESCHERICHIA COLI;

EID: 78651479441     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.22831     Document Type: Article

References (44)

1. Anderson MS, Muehlbacher M, Street IP, Proffitt J, Poulter CD. 1989. Isopentenyl diphosphate:dimethylallyl diphosphate isomerase. An improved purification of the enzyme and isolation of the gene from Saccharomyces cerevisiae. J Biol Chem 264(32):19169-19175.
2. Asadollahi MA, Maury J, Moller K, Nielsen KF, Schalk M, Clark A, Nielsen J. 2008. Production of plant sesquiterpenes in Saccharomyces cerevisiae: Effect of ERG9 repression on sesquiterpene biosynthesis. Biotechnol Bioeng 99(3):666-677.
3. Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H. 2006. Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: The Keio collection. Mol Syst Biol 2:2006 0008.
4. Cheng AX, Xiang CY, Li JX, Yang CQ, Hu WL, Wang LJ, Lou YG, Chen XY. 2007. The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes. Phytochemistry 68(12):1632-1641.
5. Datsenko KA, Wanner BL. 2000. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci USA 97(12):6640-6645.
6. El Ghachi M, Bouhss A, Blanot D, Mengin-Lecreulx D. 2004. The bacA gene of Escherichia coli encodes an undecaprenyl pyrophosphate phosphatase activity. J Biol Chem 279(29):30106-30113.
7. Faulkner A, Chen X, Rush J, Horazdovsky B, Waechter CJ, Carman GM, Sternweis PC. 1999. The LPP1 and DPP1 gene products account for most of the isoprenoid phosphate phosphatase activities in Saccharomyces cerevisiae. J Biol Chem 274(21):14831-14837.
8. Fujisaki S, Hara H, Nishimura Y, Horiuchi K, Nishino T. 1990. Cloning and nucleotide sequence of the ispA gene responsible for farnesyl diphosphate synthase activity in Escherichia coli. J Biochem 108(6):995-1000.
9. Fujisaki S, Takahashi I, Hara H, Horiuchi K, Nishino T, Nishimura Y. 2005. Disruption of the structural gene for farnesyl diphosphate synthase in Escherichia coli. J Biochem 137(3):395-400.
10. Funk CR, Zimniak L, Dowhan W. 1992. The pgpA and pgpB genes of Escherichia coli are not essential: Evidence for a third phosphatidylglycerophosphate phosphatase. J Bacteriol 174(1):205-213.
11. Goldberg L, Haklai R, Bauer V, Heiss A, Kloog Y. 2009. New derivatives of farnesylthiosalicylic acid (salirasib) for cancer treatment: Farnesylthiosalicylamide inhibits tumor growth in nude mice models. J Med Chem 52(1):197-205.
12. Holtz KM, Kantrowitz ER. 1999. The mechanism of the alkaline phosphatase reaction: Insights from NMR, crystallography and site-specific mutagenesis. FEBS Lett 462(1-2):7-11.
13. Icho T. 1988. Membrane-bound phosphatases in Escherichia coli: Sequence of the pgpB gene and dual subcellular localization of the pgpB product. J Bacteriol 170(11):5117-5124.
14. Karlgren S, Pettersson N, Nordlander B, Mathai JC, Brodsky JL, Zeidel ML, Bill RM, Hohmann S. 2005. Conditional osmotic stress in yeast: A system to study transport through aquaglyceroporins and osmostress signaling. J Biol Chem 280(8):7186-7193.
15. Kim CM, Goldstein JL, Brown MS. 1992. cDNA cloning of MEV, a mutant protein that facilitates cellular uptake of mevalonate, and identification of the point mutation responsible for its gain of function. J Biol Chem 267(32):23113-23121.
16. Kovach ME, Elzer PH, Hill DS, Robertson GT, Farris MA, Roop RM II, Peterson KM. 1995. Four new derivatives of the broad-host-range cloning vector pBBR1MCS, carrying different antibiotic-resistance cassettes. Gene 166(1):175-176.
17. Lapczynski A, Bhatia SP, Letizia CS, Api AM. 2008. Fragrance material review on farnesol. Food Chem Toxicol 46:S149-S156.
18. Lee H, Finckbeiner S, Yu JS, Wiemer DF, Eisner T, Attygalle AB. 2007. Characterization of (E,E)-farnesol and its fatty acid esters from anal scent glands of nutria (Myocastor coypus) by gas chromatographymass spectrometry and gas chromatography-infrared spectrometry. J Chromatogr A 1165:136-143.
19. Leon R, Martin M, Vigara J, Vilchez C, Vega JM. 2003. Microalgae mediated photoproduction of beta-carotene in aqueous-organic two phase systems. Biomol Eng 20(4-6):177-182.
20. Mackie H, Overton KH. 1977. Hydrolysis and isomerization of trans,transfarnesyl diphosphate by Andrographis tissue-culture enzymes. Eur J Biochem 77(1):101-106.
21. Martin VJ, Yoshikuni Y, Keasling JD. 2001. The in vivo synthesis of plant sesquiterpenes by Escherichia coli. Biotechnol Bioeng 75(5):497-503.
22. Martin VJ, Pitera DJ, Withers ST, Newman JD, Keasling JD. 2003. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol 21(7):796-802.
23. Mille Y, Beney L, Gervais P. 2005. Compared tolerance to osmotic stress in various microorganisms: Towards a survival prediction test. Biotechnol Bioeng 92(4):479-484.
24. Muramatsu M, Ohto C, Obata S, Sakuradani E, Shimizu S. 2008a. Accumulation of prenyl alcohols by terpenoid biosynthesis inhibitors in various microorganisms. Appl Microbiol Biotechnol 80(4):589-595.
25. Muramatsu M, Ohto C, Obata S, Sakuradani E, Shimizu S. 2008b. Various oils and detergents enhance the microbial production of farnesol and related prenyl alcohols. J Biosci Bioeng 106(3):263-267.
26. Muramatsu M, Ohto C, Obata S, Sakuradani E, Shimizu S. 2009. Alkaline pH enhances farnesol production by Saccharomyces cerevisiae. J Biosci Bioeng 108(1):52-55.
27. Newman JD, Marshall J, Chang M, Nowroozi F, Paradise E, Pitera D, Newman KL, Keasling JD. 2006. High-level production of amorpha-4,11-diene in a two-phase partitioning bioreactor of metabolically engineered Escherichia coli. Biotechnol Bioeng 95(4):684-691.
28. Nickerson KW, Atkin AL, Hornby JM. 2006. Quorum sensing in dimorphic fungi: Farnesol and beyond. Appl Environ Microbiol 72(6):3805-3813.
29. Ohto C, Muramatsu M, Obata S, Sakuradani E, Shimizu S. 2009a. Overexpression of the gene encoding HMG-CoA reductase in Saccharomyces cerevisiae for production of prenyl alcohols. Appl Microbiol Biotechnol 82(5):837-845.
30. Ohto C, Muramatsu M, Obata S, Sakuradani E, Shimizu S. 2009b. Prenyl alcohol production by expression of exogenous isopentenyl diphosphate isomerase and farnesyl diphosphate synthase genes in Escherichia coli. Biosci Biotechnol Biochem 73(1):186-188.
31. Passariello C, Forleo C, Micheli V, Schippa S, Leone R, Mangani S, Thaller MC, Rossolini GM. 2006. Biochemical characterization of the class B acid phosphatase (AphA) of Escherichia coli MG1655. Biochim Biophys Acta 1764(1):13-19.
32. Rude MA, Schirmer A. 2009. New microbial fuels: A biotech perspective. Curr Opin Microbiol 12(3):274-281.
33. Sambrook J, Russell DW. 2001. Molecular cloning. New York: Cold Spring Harbor Laboratory Press.
34. Shea JM, Del Poeta M. 2006. Lipid signaling in pathogenic fungi. Curr Opin Microbiol 9(4):352-358.
35. Shirtliff ME, Krom BP, Meijering RA, Peters BM, Zhu J, Scheper MA, Harris ML, Jabra-Rizk MA. 2009. Farnesol-induced apoptosis in Candida albicans. Antimicrob Agents Chemother 53(6):2392-2401.
36. Song L. 2003. Detection of farnesyl diphosphate accumulation in yeast ERG9 mutants. Anal Biochem 317(2):180-185.
37. Song L. 2006. A soluble form of phosphatase in Saccharomyces cerevisiae capable of converting farnesyl diphosphate into E,E-farnesol. Appl Biochem Biotechnol 128(2):149-158.
38. Takahashi S, Yeo Y, Greenhagen BT, McMullin T, Song L, Maurina-Brunker J, Rosson R, Noel JP, Chappell J. 2007. Metabolic engineering of sesquiterpene metabolism in yeast. Biotechnol Bioeng 97(1):170-181.
39. Touze T, Blanot D, Mengin-Lecreulx D. 2008. Substrate specificity and membrane topology of Escherichia coli PgpB, an undecaprenyl pyrophosphate phosphatase. J Biol Chem 283(24):16573-16583.
40. Verhoef S, Wierckx N, Westerhof RG, de Winde JH, Ruijssenaars HJ. 2009. Bioproduction of p-hydroxystyrene from glucose by the solventtolerant bacterium Pseudomonas putida S12 in a two-phase waterdecanol fermentation. Appl Environ Microbiol 75(4):931-936.
41. Withers ST, Gottlieb SS, Lieu B, Newman JD, Keasling JD. 2007. Identification of isopentenol biosynthetic genes from Bacillus subtilis by a screening method based on isoprenoid precursor toxicity. Appl Environ Microbiol 73(19):6277-6283.
42. Yoon SH, Park HM, Kim JE, Lee SH, Choi MS, Kim JY, Oh DK, Keasling JD, Kim SW. 2007. Increased beta-carotene production in recombinant Escherichia coli harboring an engineered isoprenoid precursor pathway with mevalonate addition. Biotechnol Prog 23(3):599-605.
43. Yoon SH, Lee SH, Das A, Ryu HK, Jang HJ, Kim JY, Oh DK, Keasling JD, Kim SW. 2009. Combinatorial expression of bacterial whole mevalonate pathway for the production of beta-carotene in E. coli. J Biotechnol 140(3-4):218-226.
44. Zahiri HS, Yoon SH, Keasling JD, Lee SH, Won Kim S, Yoon SC, Shin YC. 2006. Coenzyme Q10 production in recombinant Escherichia coli strains engineered with a heterologous decaprenyl diphosphate synthase gene and foreign mevalonate pathway. Metab Eng 8(5):406-416.