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2015 | OriginalPaper | Buchkapitel

Isoprene

verfasst von : Claudia E. Vickers, Suriana Sabri

Erschienen in: Biotechnology of Isoprenoids

Verlag: Springer International Publishing

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Abstract

Isoprene is a volatile C₅ hydrocarbon. It is produced by a wide variety of organisms and has been shown to play a role in protection of plants under abiotic stress conditions. It also has many different uses as an industrial chemical: most notably as a precursor for synthetic rubbers, but also for production of elastomers, copolymers, adhesives, and specialised chemicals. Modifying and/or engineering isoprene production in plants has the potential to contribute to engineered stress resistance. Moreover, as petrochemical sources of isoprene increase in price and become more scarce, bioproduction routes through microbial processes are becoming more attractive. Here we examine biotechnological aspects of isoprene production and review the current state of the art for both microbial-based industrial bioprocesses and plant engineering.

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Vorheriges Kapitel Bioprocess Engineering for Microbial Synthesis and Conversion of Isoprenoids

Nächstes Kapitel Biosynthesis and Biotechnology of High-Value p-Menthane Monoterpenes, Including Menthol, Carvone, and Limonene

Ajikumar PK, Tyo K, Carlsen S, Mucha O, Phon TH, Stephanopoulos G (2008) Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms. Mol Pharm 5(2):167–190. doi:10.1021/mp700151b

Ajikumar PK, Xiao W-H, Tyo KEJ, Wang Y, Simeon F, Leonard E, Mucha O, Phon TH, Pfeifer B, Stephanopoulos G (2010) Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330(6000):70–74. doi:10.1126/science.1191652

Albrecht M, Misawa N, Sandmann G (1999) Metabolic engineering of the terpenoid biosynthetic pathway of Escherichia coli for production of the carotenoids β-carotene and zeaxanthin. Biotechnol Lett 21(9):791–795

Alper H, Jin YS, Moxley JF, Stephanopoulos G (2005) Identifying gene targets for the metabolic engineering of lycopene biosynthesis in Escherichia coli. Metab Eng 7(3):155–164. doi:10.1016/j.ymben.2004.12.003

Alper H, Miyaoku K, Stephanopoulos G (2005) Construction of lycopene-overproducing E. coli strains by combining systematic and combinatorial gene knockout targets. Nat Biotechnol 23(5):612–616

Anderson S (2013) Methods for the direct conversion of carbon dioxide into a hydrocarbon using a metabolically engineering photosynthetic organism. USA Patent US8609385, 17 Dec 2013

Archer C, Kim J, Jeong H, Park J, Vickers C, Lee S, Nielsen L (2011) The genome sequence of E. coli W ATCC 9637: comparative genome analysis and an improved genome-scale model of E. coli. BMC Genomics 12(9):9. doi:10.1186/1471-2164-1112-1189

Arifin Y, Archer C, Lim S, Quek L-E, Sugiarto H, Marcellin E, Vickers C, Krömer J, Nielsen L (2014) Escherichia coli W shows fast, highly oxidative sucrose metabolism and low acetate formation. Appl Microbiol Biotechnol 98(21):9033–9044. doi:10.1007/s00253-014-5956-4

Arifin Y, Sabri S, Sugiarto H, Krömer JO, Vickers CE, Nielsen LK (2011) Deletion of cscR in Escherichia coli W improves growth and poly-3-hydroxyburyrate (PHB) production from sucrose in fed batch culture. J Biotechnol 156:275. doi:10.1016/j.jbiotec.2011.07.003

10.

Artsatbanov VY, Vostroknutova GN, Shleeva MO, Goncharenko AV, Zinin AI, Ostrovsky DN, Kapreliants AS (2012) Influence of oxidative and nitrosative stress on accumulation of diphosphate intermediates of the non-mevalonate pathway of isoprenoid biosynthesis in corynebacteria and mycobacteria. Biochemistry 77(4):362–371. doi:10.1134/S0006297912040074

11.

Banerjee A, Sharkey TD (2014) Methylerythritol 4-phosphate (MEP) pathway metabolic regulation. Nat Prod Rep. doi:10.1039/C3NP70124G

12.

Banerjee A, Wu Y, Banerjee R, Li Y, Yan H, Sharkey TD (2013) Feedback inhibition of deoxy-D-xylulose 5-phosphate synthase regulates the methyl erythritol 4-phosphate pathway. J Biol Chem 288(23):16926–16936. doi:10.1074/jbc.M113.464636

13.

Beatty MK, Hayes K, Hou Z, Meyer DJ, Nannapaneni K, Rife CL, Wells DH, Zastrow-Hayes GM (2013) Legume isoprene synthase for production of isoprene. USA Patent US 20130330709, 12 Dec 2013

14.

Beck ZQ, Bott RR, Rife CL, Wells D, Miller JV (2013) Three-dimensional structure of isoprene synthase and its use thereof for generating variants. USA Patent US8518686, 27 Aug 2013

15.

Beck ZQ, Calabria AR, Miller MC, Vaviline DV, Nielsen AT (2013) Increased isoprene production using the archaeal lower mevalonate pathway. USA Patent US8361762, 29 Jan 2013

16.

Beck ZQ, Cervin MA, Nielsen AT, Peres CM (2013) Compositions and methods of PGL for the increased production of isoprene. USA Patent US8455236B2, 4 Jun 2013

17.

Beck ZQ, Eliot AC, Peres CM, Vaviline DV (2013) Utilization of phosphoketolase in the production of mevalonate, isoprenoid precursors, and isoprene. Application US20130089906, 11 April 2013

18.

Behnke K, Ehlting B, Teuber M, Bauerfeind M, Louis S, Hansch R, Polle A, Bohlmann J, Schnitzler JP (2007) Transgenic, non-isoprene emitting poplars don’t like it hot. Plant J 51:485–499

19.

Behnke K, Grote R, Brüggemann N, Zimmer I, Zhou G, Elobeid M, Janz D, Polle A, Schnitzler J-P (2012) Isoprene emission-free poplars—a chance to reduce the impact from poplar plantations on the atmosphere. New Phytol 194(1):70–82. doi:10.1111/j.1469-8137.2011.03979.x

20.

Behrendorff JBYH, Vickers CE, Chrysanthopoulos P, Nielsen LK (2013) 2,2-Diphenyl-1-picrylhydrazyl as a screening tool for recombinant monoterpene biosynthesis. Microb Cell Fact 12:76. doi:10.1186/1475-2859-12-76

21.

Bentley FK, Melis A (2012) Diffusion-based process for carbon dioxide uptake and isoprene emission in gaseous/aqueous two-phase photobioreactors by photosynthetic microorganisms. Biotechnol Bioeng 109(1):100–109. doi:10.1002/bit.23298

22.

Bentley FK, Zurbriggen A, Melis A (2014) Heterologous expression of the mevalonic acid pathway in cyanobacteria enhances endogenous carbon partitioning to isoprene. Mol Plant 7(1):71–86. doi:10.1093/mp/sst134

23.

Blanch HW, Simmons BA, Klein-Marcuschamer D (2011) Biomass deconstruction to sugars. Biotechnol J 6(9):1086–1102. doi:10.1002/biot.201000180

24.

Boghigian BA, Salas D, Ajikumar PK, Stephanopoulos G, Pfeifer B (2012) Analysis of heterologous taxadiene production in K- and B-derived Escherichia coli. Appl Microbiol Biotechnol 93(4):1651–1661. doi:10.1007/s00253-011-3528-4

25.

Bott RR, Cervin MA, Kellis JT, Jr, McAuliffe JC, Miasnikov A, Peres CM, Rife CL, Wells DH, Weyler W, Whited GM (2012) Isoprene synthase variants for improved microbial production of isoprene. USA Patent US8173410, 8 May 2012

26.

Bramucci MG, Brzostowicz PC, Cheng Q, Kostichka KN, Rouviere PE, Nagarajan V, Tao L, Thomas SM (2006) Genes involved in isoprenoid compound production. USA Patent US7034140, 25 April 2006

27.

Bresdow S, Doneske S, Li M, Zhou H, Monticello DJ, Campbell P (2014) Microorganisms and processes for the conversion of glycerol to isoprene. Application WO2014015210 A2, 23 Jan 2014

28.

Brilli F, Barta C, Fortunati A, Centritto M, Loreto F (2006) The contribution of different carbon sources to isoprene synthesis during and after drought in Populus alba leaves. Geophys Res Abs 8:EGU06-A-04113

29.

Bruschi M, Boyes S, Sugiarto H, Nielsen LK, Vickers CE (2011) A transferrable sucrose utilization approach for non-sucrose-utilizing Escherichia coli strains. Biotech Adv 30(5):1001–1010. doi:10.1016/j.biotechadv.2011.08.019

30.

Burke C, Croteau R (2002) Geranyl diphosphate synthase from Abies grandis: cDNA isolation, functional expression, and characterization. Arch Biochem Biophys 405(1):130–136. doi:10.1016/S0003-9861(02)00335-1

31.

Calabria AR, Cervin MA, Chotani GK, La Duca R, McAuliffe JC, Miller MC, Sabo TA, Sanford KJ, Webster EL, Whited GM (2013) Compositions and methods for producing isoprene free of C5 hydrocarbons under decoupling conditions and/or safe operating ranges. USA Patent US8420360, 16 April 2013

32.

Campos N, Rodríguez-Concepción M, Sauret-Gueto S, Gallego F, Lois LM, Boronat A (2001) Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethyl allyl diphosphate from mevalonate: a novel system for the genetic analysis of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis. Biochem J 353:59–67

33.

Cervin MA, Chotani GK, Feher FJ, La Duca R, McAuliffe JC, Miasnikov A, Peres CM, Puhala AS, Sanford KJ, Valle F, Whited GM (2012) Compositions and methods for producing isoprene. USA Patent US8420360 B2, 16 Oct 2012

34.

Chae HS, Kim KH, Kim SC, Lee PC (2010) Strain-dependent carotenoid productions in metabolically engineered Escherichia coli. Appl Biochem Biotechnol 162(8):2333–2344. doi:10.1007/s12010-010-9006-0

35.

Chameides WL, Lindsay RW, Richardson J, Kiang CS (1998) The role of biogenic hydrocarbons in urban photochemical smog: atlanta as a case study. Science 241:1473–1475

36.

Chandran SS, Kealey JT, Reeves CD (2011) Microbial production of isoprenoids. Process Biochem 46(9):1703–1710. doi:10.1016/j.procbio.2011.05.012

37.

Chotani GK, McAuliffe JC, Miller MC, Muir RE, Vaviline DV, Weyler W (2013) Isoprene production using the DXP and MVA pathway. US8507235 B2, 13 Aug 2013

38.

Chotani GK, Nielsen A, Sanford KJ (2013) Reduction of carbon dioxide emission during isoprene production by fermentation. WO/2010/031068

39.

Claeys M, Graham B, Vas G, Wang W, Vermeylen R, Pashynska V, Cafmeyer J, Guyon P, Andreae MO, Artaxo P, Maenhaut W (2004) Formation of secondary organic aerosols through photooxidation of isoprene. Science 303(5661):1173–1176

40.

Coelho PS, Farrow MF, Smith MA (2014) De novo metabolic pathways for isoprene biosynthesis. World intellectual property organisation patent application WO2014066892 A1, 1 May 2014

41.

Dellas N, Thomas ST, Manning G, Noel JP, Weigel D (2013) Discovery of a metabolic alternative to the classical mevalonate pathway. eLife 2:e00672. doi:10.7554/eLife.00672

42.

Dionisi D, Anderson JA, Aulenta F, McCue A, Paton G (2014) The potential of microbial processes for lignocellulosic biomass conversion to ethanol: a review. J Chem Technol Biotechnol. doi:10.1002/jctb.4544

43.

Djaman O, Outten FW, Imlay JA (2004) Repair of oxidized iron-sulphur clusters in Escherichia coli. J Biol Chem 279(43):44590–44599. doi:10.1074/jbc.M406487200

44.

Durnin G, Clomburg J, Yeates Z, Alvarez PJJ, Zygourakis K, Campbell P, Gonzalez R (2009) Understanding and harnessing the microaerobic metabolism of glycerol in Escherichia coli. Biotechnol Bioeng 103(1):148–161. doi:10.1002/bit.22246

45.

Eisenreich W, Bacher A, Arigoni D, Rohdich F (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci V61(12):1401–1426

46.

Fall R, Copley SD (2000) Bacterial sources and sinks of isoprene, a reactive atmospheric hydrocarbon. Environ Microbiol 2(2):123–130

47.

Fall R, Wildermuth MC (1998) Isoprene synthase: from biochemical mechanism to emission algorithm. J Geophys Res 103(D19):25599–25610

48.

Farmer WR, Liao JC (2001) Precursor balancing for metabolic engineering of lycopene production in Escherichia coli. Biotechnol Progr 17(1):57–61

49.

Fortunati A, Barta C, Brilli F, Centritto M, Zimmer I, Schnitzler JP, Loreto F (2008) Isoprene emission is not temperature-dependent during and after severe drought-stress: a physiological and biochemical analysis. Plant J 55(4):687–697

50.

Goldstein JL, Brown MS (1990) Regulation of the mevalonate pathway. Nature 343(6257):425–430

51.

Gräwert T, Kaiser J, Zepeck F, Laupitz R, Hecht S, Amslinger S, Schramek N, Schleicher E, Weber S, Haslbeck M, Buchner J, Rieder C, Arigoni D, Bacher A, Eisenreich W, Rohdich F (2004) IspH protein of Escherichia coli: studies on iron–sulfur cluster implementation and catalysis. J Am Chem Soc 126(40):12847–12855. doi:10.1021/ja0471727

52.

Gray DW, Breneman SR, Topper LA, Sharkey TD (2011) Biochemical characterization and homology modelling of methylbutenol synthase and implications for understanding hemiterpene synthase evolution in plants. J Biol Chem 286(23):20582–20590. doi:10.1074/jbc.M111.237438

53.

Guenther A, Karl T, Harley P, Wiedinmyer C, Palmer PI, Geron C (2006) Estimates of global terrestrial isoprene emissions using MEGAN (model of emissions of gases and aerosols from nature). Atmos Chem Phys 6:3181–3210

54.

Hansegard J (2010) Sugar plus science equals $150,000 tires. Wall Street J, 8 Dec 2010, http://online.wsj.com/news/articles/SB10001424052748703493504576007112633560914

55.

Harker M, Bramley PM (1999) Expression of prokaryotic 1-deoxy-D-xylulose-5-phosphatases in Escherichia coli increases carotenoid and ubiquinone biosynthesis. FEBS Letters 448(1):115–119. doi:10.1016/s0014-5793(99)00360-9

56.

Harley P, Guenther A, Zimmerman P (1996) Effects of light, temperature and canopy position on net photosynthesis and isoprene emission from sweetgum (Liquidambar styraciflua) leaves. Tree Physiol 16(1–2):25–32

57.

Hayashi Y, Harada M, Takaoka S, Fukushima Y, Yokoyama K, Nishio Y, Tajima Y, Mihara Y, Nakata K (2014) Isoprene synthase and gene encoding the same, and method for producing isoprene monomer. USA Patent Application Number US2014/0113344

58.

Hemmerlin A (2013) Post-translational events and modifications regulating plant enzymes involved in isoprenoid precursor biosynthesis. Plant Sci 203–204:41–54

59.

Hewitt CN, MacKenzie AR, Di Carlo P, Di Marco CF, Dorsey JR, Evans M, Fowler D, Gallagher MW, Hopkins JR, Jones CE, Langford B, Lee JD, Lewis AC, Lim SF, McQuaid J, Misztal P, Moller SJ, Monks PS, Nemitz E, Oram DE, Owen SM, Phillips GJ, Pugh TAM, Pyle JA, Reeves CE, Ryder J, Siong J, Skiba U, Stewart DJ (2009) Nitrogen management is essential to prevent tropical oil palm plantations from causing ground-level ozone pollution. Proc Natl Acad Sci USA 106(44):18447–18451. doi:10.1073/pnas.0907541106

60.

Hewitt CN, Street RA, Scholefield PA (2004) Biogenic VOC Emission Database. Lancaster University. http://www.es.lancs.ac.uk/cnhgroup/download.html. Accessed on 6 Oct 2014

61.

Hong S-Y, Zurbriggen AS, Melis A (2012) Isoprene hydrocarbons production upon heterologous transformation of Saccharomyces cerevisiae. J Appl Microbiol 113(1):52–65. doi:10.1111/j.1365-2672.2012.05319.x

62.

Jiang M, Stephanopoulos G, Pfeifer BA (2012) Toward biosynthetic design and implementation of Escherichia coli-derived paclitaxel and other heterologous polyisoprene compounds. Appl Environ Microbiol 78(8):2497–2504. doi:10.1128/aem.07391-11

63.

Jones CA, Rasmussen RA (1975) Production of isoprene by leaf tissue. Plant Physiol 55(6):982–987

64.

Julsing M, Rijpkema M, Woerdenbag H, Quax W, Kayser O (2007) Functional analysis of genes involved in the biosynthesis of isoprene in Bacillus subtilis. Appl Microbiol Biotechnol 75:1377–1384

65.

Kesselmeier J, Staudt M (1999) Biogenic volatile organic compounds (VOC): an overview on emission, physiology and ecology. J Atmos Chem V33(1):23–88

66.

Kim YS, Lee JH, Kim NH, Yeom SJ, Kim SW, Oh DK (2011) Increase of lycopene production by supplementing auxiliary carbon sources in metabolically engineered Escherichia coli. Appl Microbiol Biotechnol 90(2):489–497. doi:10.1007/s00253-011-3091-z

67.

Klein-Marcuschamer D, Ajikumar PK, Stephanopoulos G (2007) Engineering microbial cell factories for biosynthesis of isoprenoid molecules: beyond lycopene. Trends Biotechnol 25(9):417–424

68.

Köksal M, Zimmer I, Schnitzler JP, Christianson DW (2010) Structure of isoprene synthase illuminates the chemical mechanism of teragram atmospheric carbon emission. J Mol Biol 402(2):363–373

69.

Kuzma J, Fall R (1993) Leaf isoprene emission rate is dependent on leaf development and the level of isoprene synthase. Plant Physiol 101(2):435–440

70.

Kuzma J, Nemecek M, Pollock WH, Fall R (1995) Bacteria produce the volatile hydrocarbon isoprene. Curr Microbiol V30(2):97–103

71.

Laothawornkitkul J, Paul ND, Vickers CE, Possell M, Mullineaux PM, Hewitt CN, Taylor JE (2008) The role of isoprene in insect herbivory. Plant Signal Behav 3(12):1141–1142

72.

Laothawornkitkul J, Paul ND, Vickers CE, Possell M, Taylor JE, Mullineaux PM, Hewitt CN (2008) Isoprene emissions influence herbivore feeding decisions. Plant Cell Environ 31(10):1410–1415. doi:10.1111/j.1365-3040.2008.01849.x

73.

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(5):495–504. doi:10.1046/j.1365-3040.1999.00425.x

74.

Leonard E, Ajikumar PK, Thayer K, Xiao W-H, Mo JD, Tidor B, Stephanopoulos G, Prather KLJ (2010) Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control. Proc Nat Acad Sci 107(31):13654–13659. doi:10.1073/pnas.1006138107

75.

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(1):70–79. doi:10.1016/j.ymben.2009.10.001

76.

Liu H, Sun Y, Ramos KRM, Nisola GM, Valdehuesa KNG, Lee WK, Park SJ, Chung W-J (2013) Combination of entner-doudoroff pathway with MEP increases isoprene production in engineered Escherichia coli. PLoS ONE 8(12):e83290. doi:10.1371/journal.pone.0083290

77.

Loivamäki M, Mumm R, Dicke M, Schnitzler JP (2008) Isoprene interferes with the attraction of bodyguards by herbaceous plants. Proc Natl Acad Sci USA 104(45):17430–17435

78.

Loivamäki M, Gilmer F, Fischbach RJ, Sorgel C, Bachl A, Walter A, Schnitzler JP (2007) Arabidopsis, a model to study biological functions of isoprene emission? Plant Physiol 144:1066–1078

79.

Lombard J, Moreira D (2011) Origins and early evolution of the mevalonate pathway of isoprenoid biosynthesis in the three domains of life. Mol Biol Evol 28(1):87–99. doi:10.1093/molbev/msq177

80.

Loreto F, Mannozzi M, Maris C, Nascetti P, Ferranti F, Pasqualini S (2001) Ozone quenching properties of isoprene and its antioxidant role in leaves. Plant Physiol 126(3):993–1000

81.

Marienhagen J, Bott M (2013) Metabolic engineering of microorganisms for the synthesis of plant natural products. J Biotechnol 163(2):166–178

82.

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. doi:10.1038/nbt833

83.

McCoy M (2008) Biobased isoprene: goodyear and genencor seek a fermentation route to important synthetic rubber raw material. Chem Eng News 86:15

84.

Meskhidze N, Nenes A (2006) Phytoplankton and cloudiness in the southern ocean. Science 314(5804):1419–1423. doi:10.1126/science.1131779

85.

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(3):483–487. doi:10.1007/s004250100557

86.

Monson RK, Fall R (1989) Isoprene emission from aspen leaves: influence of environment and relation to photosynthesis and photorespiration. Plant Physiol 90(1):267–274

87.

Monson RK, Jones RT, Rosenstiel TN, Schnitzler JP (2013) Why only some plants emit isoprene. Plant Cell Environ 36(3):503–516

88.

Muir RE, Weyler W (2014) Compositions and methods for improved isoprene production using two types of ispg enzymes. USA Patent Application US20140147902 A1

89.

Okada K, Hase T (2005) Cyanobacterial non-mevalonate pathway. (E)-4-Hyddroxy-3-methylbut-2-enyl diphosphate synthase interacts with ferredoxin in Thermosynechococcus elongatus BP-1. J Biol Chem 280(21):20672–20679. doi:10.1074/jbc.M500865200

90.

Okamura E, Tomita T, Sawa R, Nishiyama M, Kuzuyama T (2010) Unprecedented acetoacetyl-coenzyme a synthesizing enzyme of the thiolase superfamily involved in the mevalonate pathway. Proc Natl Acad Sci USA 107(25):11265–11270. doi:10.1073/pnas.1000532107

91.

Pegoraro E, Rey A, Bobich EG, Barron-Gafford G, Grieve KA, Malhi Y, Murthy R (2004) Effect of elevated CO₂ concentration and vapour pressure deficit on isoprene emission from leaves of Populus deltoides during drought. Funct Plant Biol 31(12):1137–1147

92.

Poisson N, Kanakidou M, Crutzen PJ (2000) Impact of non-methane hydrocarbons on tropospheric chemistry and the oxidizing power of the global troposphere: 3-dimensional modelling results. J Atmos Chem 36(2):157–230

93.

Ramos K, Valdehuesa K, Liu H, Nisola G, Lee W-K, Chung W-J (2014) Combining De Ley–Doudoroff and methylerythritol phosphate pathways for enhanced isoprene biosynthesis from d-galactose. Bioproc Biosys Eng, pp 1–9. doi:10.1007/s00449-014-1228-z

94.

Rasmussen R (1972) Survey of plant species that release isoprene to atmosphere. Abs Pap Am Chem Soc, 13

95.

Rasmussen RA (1970) Isoprene: identified as a forest-type emission to the atmosphere. Envir Sci Tech 4(8):667–671. doi:10.1021/es60043a008

96.

Reardon K (2014) Lignocellulosic biorefineries: concepts and possibilities. In: McCann MC, Buckeridge MS, Carpita NC (eds) Plants and bioenergy, Vol 4. Adv Plant Biol. Springer, New York, pp 255–265. doi:10.1007/978-1-4614-9329-7_15

97.

Rife CL, Wells DH (2014) Isoprene synthase variants with improved solubility for production of isoprene. USA Patent US8735134, 27 May 2014

98.

Rodríguez-Concepción 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(3):1079–1089

99.

Rodríguez-Villalón A, Perez-Gil J, Rodríguez-Concepción M (2008) Carotenoid accumulation in bacteria with enhanced supply of isoprenoid precursors by upregulation of exogenous or endogenous pathways. J Biotechnol 135(1):78–84. doi:10.1016/j.jbiotec.2008.02.023

100.

Rohmer M (2003) Mevalonate-independent methylerythritol phosphate pathway for isoprenoid biosynthesis elucidation and distribution. Pure Appl Chem 75(2–3):375–387

101.

Rude MA, Schirmer A (2009) New microbial fuels: a biotech perspective. Curr Opin Microbiol 12(3):274–281. doi:10.1016/j.mib.2009.04.004

102.

Ruzicka L (1953) The isoprene rule and the biogenesis of terpenic compounds. Experientia 9(10):357–367

103.

Ryan AC, Hewitt CN, Possell M, Vickers CE, Purnell A, Mullineaux PM, Davies WJ, Dodd IC (2014) Isoprene emission protects photosynthesis but reduces plant productivity during drought in transgenic tobacco (Nicotiana tabacum) plants. New Phytol 201(1):205–216. doi:10.1111/nph.12477

104.

Sabri S, Nielsen LK, Vickers CE (2013) Molecular control of sucrose utilization in Escherichia coli W, an efficient sucrose-utilizing strain. Appl Environ Microbiol 79(2):478–487. doi:10.1128/aem.02544-12

105.

Saltman W (ed) (1985) Isoprene Kirk-othmer concise encyclopaedia of chemical technology. Wiley, New York

106.

Sanadze GA (1957) The nature of gaseous substances emitted by leaves of Robina pseudoacacia. Soobshch Akad Nauk Gruz SSR 19:83–86

107.

Sanadze GA (1969) Light-dependent excretion of molecular isoprene by leaves. Prog Photosynth Res II:701–706

108.

Sasaki K, Ohara K, Yazaki K (2005) Gene expression and characterization of isoprene synthase from Populus alba. FEBS Lett 579(11):2514–2518. doi:10.1016/j.febslet.2005.03.066

109.

Sasaki K, Ohara K, Yazaki K (2005) Gene expression and characterization of isoprene synthase from Populus alba. FEBS Lett 579(11):2514–2518

110.

Sasaki K, Saito T, Lamsa M, Oksman-Caldentey KM, Suzuki M, Ohyama K, Muranaka T, Ohara K, Yazaki K (2007) Plants utilize isoprene emission as a thermotolerance mechanism. Plant Cell Physiol 48(9):1254–1262

111.

Schnitzler JP, Lehning A, Steinbrecher R (1997) Seasonal pattern of isoprene synthase activity in Quercus robur leaves and its significance for modeling isoprene emission rates. Bot Acta 110(3):240–243

112.

Seemann M, Bui BT, Wolff M, Tritsch D, Campos N, Boronat A, Marquet A, Rohmer M (2002) Isoprenoid biosynthesis through the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE) is a [4Fe-4S] protein. Angewandte Chemie 41(22):4337–4339. doi:10.1002/1521-3773(20021115)41:22<4337:AID-ANIE4337>3.0.CO;2-K

113.

Shallcross DE, Monks PS (2000) New Directions: a role for isoprene in biosphere-climate-chemistry feedbacks. Atmos Environ 34(10):1659–1660

114.

Sharkey TD (1996) Isoprene synthesis by plants and animals. Endeavour 20(2):74–78

115.

Sharkey TD, Gray DW, Pell HK, Breneman SR, Topper L (2013) Isoprene synthase genes form a monophyletic clade of acyclic terpene synthases in the Tps-b terpene synthase family. Evolution 67(4):1026–1040. doi:10.1111/evo.12013

116.

Sharkey TD, Loreto F (1993) Water stress, temperature, and light effects on the capacity for isoprene emission and photosynthesis of kudzu leaves. Oecologia 95(3):328–333

117.

Sharkey TD, Monson RK (2014) The future of isoprene emission from leaves, canopies and landscapes. Plant Cell Environ 37(8):1727–1740. doi:10.1111/pce.12289

118.

Sharkey TD, Singsaas EL (1995) Why plants emit isoprene. Nature 374:769

119.

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

120.

Silver GM, Fall R (1991) Enzymatic synthesis of isoprene from dimethylallyl diphosphate in aspen leaf extracts. Plant Physiol 97(4):1588–1591

121.

Silver GM, Fall R (1995) Characterization of aspen isoprene synthase, an enzyme responsible for leaf isoprene emission to the atmosphere. J Biol Chem 270(22):13010–13016

122.

Sivy TL, Fall R, Rosenstiel TN (2011) Evidence of isoprenoid precursor toxicity in Bacillus subtilis. Biosci Biotechnol Biochem 75(12):2376–2383

123.

Sivy TL, Shirk MC, Fall R (2002) Isoprene synthase activity parallels fluctuations of isoprene release during growth of Bacillus subtilis. Biochem Biophys Res Commun 294(1):71–75

124.

Stephanopoulos G, Alper HS, Jin YS (2006) Gene targets for enhanced carotenoid production. USA Patent US7741070, 22 June 2010

125.

Stephanopoulos G (2007) Challenges in engineering microbes for biofuels production. Science 315:801–804

126.

Taalman RDFM (1996) Isoprene: background and issues. Toxicology 113(1–3):242–246

127.

Takahashi S, Yeo Y, Greenhagen B, 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

128.

Tattini M, Velikova V, Vickers C, Brunetti C, Di Ferdinando M, Trivellini A, Fineschi S, Agati G, Ferrini F, Loreto F (2014) Isoprene production in transgenic tobacco alters isoprenoid, non-structural carbohydrate and phenylpropanoid metabolism, and protects photosynthesis from drought stress. Plant Cell Environ 37(8):1950–1964. doi:10.1111/pce.12350

129.

Thompson AM (1992) The oxidizing capacity of the earth’s atmosphere—probable past and future changes. Science 256(5060):1157–1165

130.

Tingey DT, Evans R, Gumpertz M (1981) Effects of environmental conditions on isoprene emission from live oak. Planta 152(6):565–570

131.

Tokumoto U, Takahashi Y (2001) Genetic analysis of the isc operon in Escherichia coli involved in the biogenesis of cellular iron-sulfur proteins. J Biochem 130(1):63–71

132.

Trainer M, Williams EJ, Parrish DD, Buhr MP, Allwine EJ, Westberg HH, Fehsenfeld FC, Liu SC (1987) Models and observations of the impact of natural hydrocarbons on rural ozone. Nature 329(6141):705–707

133.

Vickers CE, Behrendorff JBYH, Bongers M, Brennan TCR, Bruschi M, Nielsen LK (2014) Production of industrially-relevant isoprenoid compounds in engineered microbes. In: Kamm B (ed) Microorganisms in biorefineries. Springer, Heidelberg

134.

Vickers CE, Blank LM, Kromer JO (2010) Chassis cells for industrial biochemical production. Nat Chem Biol 6(12):875–877. doi:10.1038/Nchembio.484

135.

Vickers CE, Bongers M, Liu Q, Delatte T, Bouwmeester H (2014) Metabolic engineering of volatile isoprenoids in plants and microbes. Plant Cell Environ Online Early. doi:10.1111/pce.12316

136.

Vickers CE, Gershenzon J, Lerdau MT, Loreto F (2009) A unified mechanism of action for volatile isoprenoids in plant abiotic stress. Nat Chem Biol 5(5):283–291. doi:10.1038/Nchembio.158

137.

Vickers CE, Klein-Marcuschamer D, Krömer JO (2012) Examining the feasibility of bulk commodity production in Escherichia coli. Biotechnol Lett 34(4):585

138.

Vickers CE, Possell M, Cojocariu CI, Velikova VB, Laothawornkitkul J, Ryan A, Mullineaux PM, Hewitt CN (2009) Isoprene synthesis protects transgenic tobacco plants from oxidative stress. Plant Cell Environ 32(5):520–531. doi:10.1111/j.1365-3040.2009.01946.x

139.

Vickers CE, Possell M, Hewitt CN, Mullineaux PM (2010) Genetic structure and regulation of isoprene synthase in poplar (Populus spp.). Plant Mole Biol 73(4–5):547–558

140.

Vickers CE, Possell M, Laothawornkitkul J, Ryan AC, Hewitt CN, Mullineaux PM (2011) Isoprene synthesis in plants: lessons from a transgenic tobacco model. Plant Cell Environ 34(6):1043–1053. doi:10.1111/j.1365-3040.2011.02303.x

141.

Wang HH, Isaacs FJ, Carr PA, Sun ZZ, Xu G, Forest CR, Church GM (2009) Programming cells by multiplex genome engineering and accelerated evolution. Nature 460(7257):894–898. doi:10.1038/nature08187

142.

Whited GM, Feher FJ, Benko DA, Cervin MA, Chotani GK, McAuliffe JC, LaDuca RJ, Ben-Shoshan EA, Sanford KJ (2010) Development of a gas-phase bioprocess for isoprene-monomer production using metabolic pathway engineering. Ind Biotechnol 6(3):152–163. doi:10.1089/ind.2010.6.152

143.

Wiedinmyer C, Tie X, Guenther A (2006) Future changes in biogenic isoprene emissions: how might they affect regional and global atmospheric chemistry? Earth Interact 10:1–9

144.

Wildermuth MC, Fall R (1996) Light-dependent isoprene emission (characterization of a thylakoid-bound isoprene synthase in Salix discolor chloroplasts). Plant Physiol 112(1):171–182

145.

Wildermuth MC, Fall R (1998) Biochemical characterization of stromal and thylakoid-bound isoforms of isoprene synthase in willow leaves. Plant Physiol 116(3):1111–1123

146.

Williams CG (1859) On isoprene and caoutchine. Proc R Soc London 10:516–519. doi:10.1098/rspl.1859.0101

147.

Williams DC, McGarvey DJ, Katahira EJ, Croteau R (1998) Truncation of limonene synthase preprotein provides a fully active ‘Pseudomature’ form of this monoterpene cyclase and reveals the function of the amino-terminal arginine pair. Biochemistry 37(35):12213–12220

148.

Willke T, Vorlop K (2008) Biotransformation of glycerol into 1,3-propanediol. Eur J Lipid Sci Tech 110(9):831–840. doi:10.1002/ejlt.200800057

149.

Willrodt C, David C, Cornelissen S, B BH, Julsing MK, Schmid A (2014) Engineering the productivity of recombinant Escherichia coli for limonene formation from glycerol in minimal media. Biotechnol J. doi:10.1002/biot.201400023

150.

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

151.

Wolfertz M, Sharkey TD, Boland W, Kühnemann F (2004) Rapid regulation of the methylerythritol 4-phosphate pathway during isoprene synthesis. Plant Physiol 135(4):1939–1945

152.

Wolff M, Seemann M, Tse Sum Bui B, Frapart Y, Tritsch D, Garcia Estrabot A, Rodriguez-Concepcion M, Boronat A, Marquet A, Rohmer M (2003) Isoprenoid biosynthesis via the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate reductase (LytB/IspH) from Escherichia coli is a (4Fe-4S) protein. FEBS Lett 541(1–3):115–120

153.

Zhao J, Li Q, Sun T, Zhu X, Xu H, Tang J, Zhang X, Ma Y (2013a) Engineering central metabolic modules of Escherichia coli for improving β-carotene production. Metab Eng 17 (0):42–50. doi:http://dx.doi.org/10.1016/j.ymben.2013.02.002

154.

Zhao L, W-c Chang, Xiao Y, H-w Liu, Liu P (2013) Methylerythritol phosphate pathway of isoprenoid biosynthesis. Ann Rev Biochem 82(1):497–530. doi:10.1146/annurev-biochem-052010-100934

155.

Zhao Y, Yang J, Qin B, Li Y, Sun Y, Su S, Xian M (2011) Biosynthesis of isoprene in Escherichia coli via methylerythritol phosphate (MEP) pathway. Appl Microbiol Biotechnol 90(6):1915–1922. doi:10.1007/s00253-011-3199-1

156.

Zhou K, Zou RY, Stephanopoulos G, Too HP (2012) Metabolite profiling identified methylerythritol cyclodiphosphate efflux as a limiting step in microbial isoprenoid production. PLOS ONE 7(11):e47513. doi:10.1371/journal.pone.0047513

157.

Zurbriggen A, Kirst H, Melis A (2012) Isoprene production via the mevalonic acid pathway in Escherichia coli (Bacteria). BioEnergy Res 5:814–828. doi:10.1007/s12155-012-9192-4

Titel: Isoprene
verfasst von: Claudia E. Vickers
Suriana Sabri
Verlag: Springer International Publishing
Buch: Biotechnology of Isoprenoids
Print ISBN: 978-3-319-20106-1

Electronic ISBN: 978-3-319-20107-8

Copyright-Jahr: 2015
DOI: https://doi.org/10.1007/10_2014_303

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