Biosynthesis of isoprene in Escherichia coli via methylerythritol phosphate (MEP) pathway

Arnold K, Bordoli L, Kopp J, Schwede T (2006) The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics 22:195–201 Berenguer J, Calderon V, Herce M, Sanchez J (1991) Spoilage of a bakery product by isoprene-producing molds. Rev Agroquim Technol Aliment 31:580–583 Bloch K (1992) Sterol molecule: structure, biosynthesis, and function. Steroids 57:378–383 Cervin MA, Whited GM, Chotani GK, Valle F, Fioresi C, Sanford KJ, Mcauliffe JC, Feher FJ, Puhala AS, Miasnikov A, Aldor IS (2009) Compositions and methods for producing isoprene. United States patent 12/335,071 Clomburg JM, Gonzalez R (2010) Biofuel production in Escherichia coli: the role of metabolic engineering and synthetic biology. Appl Microbiol Biotechnol 86:419–434 David S, Estramareix B, Fischer JC, Thérisod M (1981) 1-Deoxy-d-threo-2-pentulose: the precursor of the five-carbon chain of the thiazole of thiamine. J Am Chem Soc 103:7341–7342 David S, Estramareix B, Fischer JC, Thérisod M (1982) The biosynthesis of thiamine. Syntheses of [1, 1, 1, 5–2H 4]-1-deoxy-d-threo-2-pentulose and incorporation of this sugar in biosynthesis of thiazole by Escherichia coli cells. J Chem Soc Perkin Trans 1:2131–2137 Eisenreich W, Bacher A, Arigoni D, Rohdich F (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci 61:1401–1426 Goldstein J, Brown M (1990) Regulation of the mevalonate pathway. Nature 343:425–430 Guex N, Peitsch M (1997) SWISS–MODEL and the Swiss–Pdb Viewer: an environment for comparative protein modeling. Electrophoresis 18:2714–2723 Harker M, Bramley P (1999) Expression of prokaryotic 1-deoxy-d-xylulose-5-phosphatases in Escherichia coli increases carotenoid and ubiquinone biosynthesis. FEBS Lett 448:115–119 Hill RE, Sayer BG, Spenser ID (1989) Biosynthesis of vitamin B6: incorporation of d-1-deoxyxylulose. J Am Chem Soc 111:1916–1917 Hill RE, Himmeldirk K, Kennedy IA, Pauloski RM, Sayer BG, Wolf E, Spenser ID (1996) The biogenetic anatomy of vitamin B6. A 13C NMR investigation of the biosynthesis of pyridoxol in Escherichia coli. J Biol Chem 271:30426–30435 Himmeldirk K, Kennedy IA, Hill RE, Sayer BG, Spenser ID (1996) Biosynthesis of vitamins B1 and B6 in Escherichia coli: concurrent incorporation of 1-deoxy-d-xylulose into thiamin (B1) and pyridoxol (B6). Chem Commun 1996:1187–1188 Hunter WN (2007) The non-mevalonate pathway of isoprenoid precursor biosynthesis. J Biol Chem 282:21573–21577 Julsing MK, Rijpkema M, Woerdenbag HJ, Quax WJ, Kayser O (2007) Functional analysis of genes involved in the biosynthesis of isoprene in Bacillus subtilis. Appl Microbiol Biotechnol 75:1377–1384 Kesselmeier J, Staudt M (1999) Biogenic volatile organic compounds (VOC): an overview on emission, physiology and ecology. J Atmos Chem 33:23–88 Kim SW, Keasling JD (2001) Metabolic engineering of the nonmevalonate isopentenyl diphosphate synthesis pathway in Escherichia coli enhances lycopene production. Biotechnol Bioeng 72:408–415 Kuzma J, Nemecek-Marshall M, Pollock WH, Fall R (1995) Bacteria produce the volatile hydrocarbon isoprene. Curr Microbiol 30:97–103 Kuzuyama T, Takagi M, Takahashi S, Seto H (2000) Cloning and characterization of 1-deoxy-d-xylulose 5-phosphate synthase from Streptomyces sp. strain CL190, which uses both the mevalonate and nonmevalonate pathways for isopentenyl diphosphate biosynthesis. J Bacteriol 182:891–897 Lehning A, Zimmer I, Steinbrecher R, Brüggemann N, Schnitzler JP (1999) Isoprene synthase activity and its relation to isoprene emission in Quercus robur L. leaves. Plant Cell Environ 22:495–504 Leonard E, Lim KH, Saw PN, Koffas MAG (2007) Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microb 73:3877–3886 Lichtenthaler HK (2000) Non-mevalonate isoprenoid biosynthesis: enzymes, genes and inhibitors. Biochem Soc T 28:785–789 Lindberg P, Park S, Melis A (2010) Engineering a platform for photosynthetic isoprene production in cyanobacteria, using Synechocystis as the model organism. Metab Eng 12:70–79 Lois LM, Campos N, Putra SR, Danielsen K, Rohmer M, Boronat A (1998) Cloning and characterization of a gene from Escherichia coli encoding a transketolase-like enzyme that catalyzes the synthesis of d-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin, and pyridoxol biosynthesis. Pro Natl Acad Sci USA 95:2105–2110 Lois LM, Rodriguez-Concepcion M, Gallego F, Campos N, Boronat A (2000) Carotenoid biosynthesis during tomato fruit development: regulatory role of 1-deoxy-d-xylulose 5-phosphate synthase. Plant J 22:503–513 Lu X, Vora H, Khosla C (2008) Overproduction of free fatty acids in E. coli: implications for biodiesel production. Metab Eng 10:333–339 Martin VJJ, Pitera DJ, Withers ST, Newman JD, Keasling JD (2003) Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol 21:796–802 Melis A (2009) Solar energy conversion efficiencies in photosynthesis: minimizing the chlorophyll antennae to maximize efficiency. Plant Sci 177:272–280 Miller B, Heuser T, Zimmer W (2000) Functional involvement of a deoxy-xylulose 5-phosphate reductoisomerase gene harboring locus of Synechococcus leopoliensis in isoprenoid biosynthesis. FEBS Lett 481:221–226 Miller B, Oschinski C, Zimmer W (2001) First isolation of an isoprene synthase gene from poplar and successful expression of the gene in Escherichia coli. Planta 213:483–487 Pitera DJ, Paddon CJ, Newman JD, Keasling JD (2007) Balancing a heterologous mevalonate pathway for improved isoprenoid production in Escherichia coli. Metab Eng 9:193–207 Remize F, Andrieu E, Dequin S (2000) Engineering of the pyruvate dehydrogenase bypass in Saccharomyces cerevisiae: role of the cytosolic Mg2+ and mitochondrial K+ acetaldehyde dehydrogenases Ald6p and Ald4p in acetate formation during alcoholic fermentation. Appl Environ Microb 66:3151–3155 Rodriguez-Concepcion M, Boronat A (2002) Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics. Plant Physiol 130:1079–1089 Rohdich F, Kis K, Bacher A, Eisenreich W (2001) The non-mevalonate pathway of isoprenoids: genes, enzymes and intermediates. Curr Opin Chem Biol 5:535–540 Rohmer M (1999) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat Prod Rep 16:565–574 Rohmer M, Seemann M, Horbach S, Bringer-Meyer S, Sahms H (1996) Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. J Am Chem Soc 118:2564–2566 Sanadze JA (1957) Emission of organic matters by leaves of Robinia pseudoacacia L. Soobshch Akad Nauk Gruz SSR 19:83 Sasaki K, Ohara K, Yazaki K (2005) Gene expression and characterization of isoprene synthase from Populus alba. FEBS Lett 579:2514–2518 Schwede T, Kopp J, Guex N, Peitsch MC (2003) SWISS-MODEL: an automated protein homology-modeling server. Nucleic Acids Res 31:3381–3385 Sharkey TD, Yeh S (2001) Isoprene emission from plants. Annu Rev Plant Biol 52:407–436 Sharkey TD, Yeh S, Wiberley AE, Falbel TG, Gong D, Fernandez DE (2005) Evolution of the isoprene biosynthetic pathway in kudzu. Plant Physiol 137:700–712 Silver GM, Fall R (1991) Enzymatic synthesis of isoprene from dimethylallyl diphosphate in aspen leaf extracts. Plant Physiol 97:1588–1591 Sprenger GA, Schorken U, Wiegert T, Grolle S, De Graaf AA, Taylor SV, Begley TP, Bringer-Meyer S, Sahm H (1997) Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-d-xylulose 5-phosphate precursor to isoprenoids, thiamin, and pyridoxol. Proc Natl Acad Sci USA 94:12857–12862 Stephanopoulos G (1999) Metabolic fluxes and metabolic engineering. Metab Eng 1:1–11 Steinbüchel A (2003) Production of rubber-like polymers by microorganisms. Curr Opin Microbiol 6:261–270 Stephanopoulos G (2007) Challenges in engineering microbes for biofuels production. Science 315:801–804 Takagi M, Kuzuyama T, Takahashi S, Seto H (2000) A gene cluster for the mevalonate pathway from Streptomyces sp. strain CL190. J Bacteriol 182:4153–4157 Takahashi S, Kuzuyama T, Watanabe H, Seto H (1998) A 1-deoxy-d-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-d-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis. Proc Natl Acad Sci USA 95:9879–9884 Wattanachaisaereekul S, Lantz AE, Nielsen ML, Nielsen J (2008) Production of the polyketide 6-MSA in yeast engineered for increased malonyl-CoA supply. Metab Eng 10:246–254