Abstract
Fossil carbon sources mainly contain hydrocarbons, and these are used on a huge scale as fuel and chemicals. Producing hydrocarbons from biomass instead is receiving increased attention. Achievable yields are modest because oxygen atoms need to be removed from biomass, keeping only the lighter carbon and hydrogen atoms. Microorganisms can perform the required conversions, potentially with high selectivity, using metabolic pathways that often end with decarboxylation. Metabolic and protein engineering are used successfully to achieve hydrocarbon production levels that are relevant in a biorefinery context. This has led to pilot or demo processes for hydrocarbons such as isobutene, isoprene, and farnesene. In addition, some non-hydrocarbon fermentation products are being further converted into hydrocarbons using a final chemical step, for example, ethanol into ethene. The main advantage of direct microbial production of hydrocarbons, however, is their potentially easy recovery because they do not dissolve in fermentation broth.
References
Straathof AJJ (2014) Transformation of biomass into commodity chemicals using enzymes or cells. Chem Rev 114:1871–1908
McKenna R, Nielsen DR (2011) Styrene biosynthesis from glucose by engineered E. coli. Metab Eng 13:544–554
Schirmer A, Rude MA, Li XZ, Popova E, del Cardayre SB (2010) Microbial biosynthesis of alkanes. Science 329:559–562
Menon N, Pasztor A, Menon BRK, Kallio P, Fisher K, Akhtar MK, Leys D, Jones PR, Scrutton NS (2015) A microbial platform for renewable propane synthesis based on a fermentative butanol pathway. Biotechnol Biofuels 8:61
Rude MA, Baron TS, Brubaker S, Alibhai M, Del Cardayre SB, Schirmer A (2011) Terminal olefin (1-alkene) biosynthesis by a novel P450 fatty acid decarboxylase from jeotgalicoccus species. Appl Environ Microbiol 77:1718–1727
Rui Z, Li X, Zhu XJ, Liu J, Domigan B, Barr I, Cate JHD, Zhang WJ (2014) Microbial biosynthesis of medium-chain 1-alkenes by a nonheme iron oxidase. Proc Natl Acad Sci U S A 111:18237–18242
Qiu Y, Tittiger C, Wicker-Thomas C, Le Goff G, Young S, Wajnberg E, Fricaux T, Taquet N, Blomquist GJ, Feyereisen R (2012) An insect-specific P450 oxidative decarbonylase for cuticular hydrocarbon biosynthesis. Proc Natl Acad Sci U S A 109:14858–14863
Whited GM, Feher FJ, Benko DA, Cervin MA, Chotani GK, McAuliffe JC, LaDuca RJ, Ben-Shoshan EA, Sanford KJ (2011) Development of a gas-phase bioprocess for isoprene-monomer production using metabolic pathway engineering. Ind Biotechnol 6:152–163
George KW, Alonso-Gutierrez J, Keasling JD, Lee TS (2015) Isoprenoid drugs, biofuels, and chemicals-artemisinin, farnesene, and beyond. Adv Biochem Eng Biotechnol 148:355–389
Gogerty DS, Bobik TA (2010) Isobutene formation from 3-hydroxy-3-methylbutyrate by diphosphomevalonate decarboxylase. Appl Environ Microbiol 76:8004–8010
Rossoni L, Hall SJ, Eastham G, Licence P, Stephens G (2015) The putative mevalonate diphosphate decarboxylase from picrophilus torridus is in reality a mevalonate-3-kinase with high potential for bioproduction of isobutene. Appl Environ Microbiol 81:2625–2634
Cuellar MC, Straathof AJJ (2015) Biochemical conversion: biofuels by industrial fermentation. In: de Jong W, van Ommen JR (eds) Biomass as a sustainable energy source for the future. Wiley, Hoboken, pp. 403–440
Clever HL, Young CL (1987) IUPAC-NIST solubility database. Methane, vol 27/28. Pergamon Press, Oxford
Hayduk W (1994) IUPAC-NIST solubility database. Ethene, vol 57. Oxford University Press, Oxford
Shaw DG (1989) IUPAC-NIST solubility database. Hydrocarbons in water and seawater, Part I, vol 37. Pergamon Press, Oxford
Shaw DG (1989) IUPAC-NIST solubility database. Hydrocarbons with water and seawater, Part II, vol 38. Pergamon Press, Oxford
Shaw DG, Maczynski A, Goral M, Wisniewska-Goclowska B, Skrzecz A, Owczarek I, Blazej K, Haulait-Pirson M-C, Hefter GT, Kapuku F, Maczynska Z, Szafranski A (2006) IUPAC-NIST solubility data series. 81. Hydrocarbons with water and seawater—revised and updated. Part 10. C11 and C12 hydrocarbons with water. J Phys Chem Ref Data 35:153–203
Kleerebezem R (2014) Biochemical conversion. In: Biomass as a sustainable energy source for the future. Wiley, Hoboken, pp 441–468
Cuellar MC, van der Wielen LAM (2015) Recent advances in the microbial production and recovery of apolar molecules. Curr Opin Biotechnol 33:39–45
Heeres AS, Picone CSF, van der Wielen LAM, Cunha RL, Cuellar MC (2014) Microbial advanced biofuels production: overcoming emulsification challenges for large-scale operation. Trends Biotechnol 32:221–229
Tabur P, Dorin G 2012 Method for purifying bio-organic compounds from fermentation broth containing surfactants by temperature-induced phase inversion
Ladygina N, Dedyukhina EG, Vainshtein MB (2006) A review on microbial synthesis of hydrocarbons. Process Biochem 41:1001–1014
Morschbacker A (2009) Bio-ethanol based ethylene. Polym Rev 49:79–84
Althoff J, Biesheuvel K, De Kok A, Pelt H, Ruitenbeek M, Spork G, Tange J, Wevers R (2013) Economic feasibility of the sugar beet-to-ethylene value chain. ChemSusChem 6:1625–1630
Marlière P (2011) Method for producing an alkene comprising step of converting an alcohol by an enzymatic dehydration step. WO 2011076691
Marlière P (2011) Method for producing an alkene comprising the step of converting an alcohol by an enzymatic dehydration step. Eur Pat Appl 2336340
Shimokawa K, Kasai Z (1970) Ethylene formation from acrylic acid by a banana pulp extract. Agric Biol Chem 34:1646–1651
Abeles FB (1972) Biosynthesis and mechanism of action of ethylene. Annu Rev Plant Physiol 23:259–292
Fukuda H, Ogawa T, Tanase S (1993) Ethylene production by microorganisms. Adv Microb Physiol 35:275–306
Larsson C, Snoep JL, Norbeck J, Albers E (2011) Flux balance analysis for ethylene formation in genetically engineered Saccharomyces cerevisiae. IET Syst Biol 5:245–251
Lieberman M (1979) Biosynthesis and action of ethylene. Annu Rev Plant Physiol Plant Mol Biol 30:533–591
Ogawa T, Takahashi M, Fujii T, Tazaki M, Fukuda H (1990) The role of NADH-Fe(III)EDTA oxidoreductase in ethylene formation from 2-keto-4-methylthiobutyrate. J Ferment Bioeng 69:287–291
Fukuda H, Ogawa T, Tazaki M, Nagahama K, Fujii T, Tanase S, Morino Y (1992) 2 Reactions are simultaneously catalyzed by a single enzyme - the arginine-dependent simultaneous formation of 2 products, ethylene and succinate, from 2-oxoglutarate by an enzyme from Pseudomonas syringae. Biochem Biophys Res Commun 188:483–489
Eckert C, Xu W, Xiong W, Lynch S, Ungerer J, Tao L, Gill R, Maness P-C, Yu J (2014) Ethylene-forming enzyme and bioethylene production. Biotechnol Biofuels 7:1–11
Davis JB, Squires RM (1954) Detection of microbially produced gaseous hydrocarbons other than methane. Science 119:381–382
Pavlova ON, Bukin SV, Lomakina AV, Kalmychkov GV, Ivanov VG, Morozov IV, Pogodaeva TV, Pimenov NV, Zemskaya TI (2014) Production of gaseous hydrocarbons by microbial communities of Lake Baikal bottom sediments. Microbiology 83:798–804
Kallio P, Pasztor A, Thiel K, Akhtar MK, Jones PR (2014) An engineered pathway for the biosynthesis of renewable propane. Nat Commun 5
Fukuda H, Fujii T, Ogawa T (1984) Microbial production of C3- and C4-hydrocarbons under aerobic conditions. Agric Biol Chem 48:1679–1682
Fukuda H, Kawaoka Y, Fujii T, Ogawa T (1987) Production of a gaseous saturated hydrocarbon mixture by Rhizopus japonicus under aerobic conditions. Agric Biol Chem 51:1529–1534
Roberts ES, Vaz AD, Coon MJ (1991) Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformylation with olefin formation. Proc Natl Acad Sci 88:8963–8966
Nishida Y, Itoh H, Yamazaki A (1994) On the chemical mechanism of aldehyde metabolism by cytochrome P-450. Polyhedron 13:2473–2476
Fujii T, Ogawa T, Fukuda H (1987) Isobutene production by Rhodotorula minuta. Appl Microbiol Biotechnol 25:430–433
Fujii T, Ogawa T, Fukuda H (1985) Production of isobutene by Rhodotorula yeasts. Agric Biol Chem 49:1541–1543
Fukuda H, Fujii T, Sukita E, Tazaki M, Nagahama S, Ogawa T (1994) Reconstitution of the isobutene-forming reaction catalyzed by cytochrome P450 and P450 reductase from Rhodotorula minuta: decarboxylation with the formation of isobutene. Biochem Biophys Res Commun 201:516–522
Shimaya C, Fujii T (2000) Cytochrome P450rm of Rhodotorula functions in the β-ketoadipate pathway for dissimilation of L-phenylalanine. J Biosci Bioeng 90:465–467
van Leeuwen BNM, van der Wulp AM, Duijnstee I, van Maris AJA, Straathof AJJ (2012) Fermentative production of isobutene. Appl Microbiol Biotechnol 93:1377–1387
Marlière P (2010) Production of alkenes by enzymatic decarboxylation of 3-hydroxyalkanoic acids. WO 2010001078
Mazaleyrat S, Delcourt M, Anissimova M, Marliere P (2015) Mevalonate diphosphate decarboxylase variants. WO2015004211 (A3)
Burk MJ, Burgard AP, Osterhout RE, Sun J, Pharkya P (2012) Microorganisms for producing butadiene and methods related thereto. WO2012177710
Pearlman PS, Chen C, Botes AL (2012) Methods of producing four carbon molecules. Pat Appl WO2012174439
Araujo AS, Souza MJB, Fernandes VJ, Diniz JC (1999) Kinetic study of isopropanol dehydration over silicoaluminophosphate catalyst. React Kinet Catal Lett 66:141–146
McCoy M (2010) Braskem plans green propylene. Chem Eng News 88:11–11
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
Singh R (2010) Facts, growth, and opportunities in industrial biotechnology. Org Process Res Dev 15:175–179
Feher FJ, Kan JK, MacAuliffe JC, McCall TF, Rodewald S, Sabo TA, Wong TH, Ploetz CD, Pickert LJ (2011) Purification of isoprene from renewable resources. US20110178261 (A1)
Morais ARC, Dworakowska S, Reis A, Gouveia L, Matos CT, Bogdal D, Bogel-Lukasik R (2015) Chemical and biological-based isoprene production: green metrics. Catal Today 239:38–43
Rabinovitch-Deere CA, Oliver JW, Rodriguez GM, Atsumi S (2013) Synthetic biology and metabolic engineering approaches to produce biofuels. Chem Rev 113:4611–4632
Paddon CJ, Westfall PJ, Pitera DJ, Benjamin K, Fisher K, McPhee D, Leavell MD, Tai A, Main A, Eng D, Polichuk DR, Teoh KH, Reed DW, Treynor T, Lenihan J, Fleck M, Bajad S, Dang G, Dengrove D, Diola D, Dorin G, Ellens KW, Fickes S, Galazzo J, Gaucher SP, Geistlinger T, Henry R, Hepp M, Horning T, Iqbal T, Jiang H, Kizer L, Lieu B, Melis D, Moss N, Regentin R, Secrest S, Tsuruta H, Vazquez R, Westblade LF, Xu L, Yu M, Zhang Y, Zhao L, Lievense J, Covello PS, Keasling JD, Reiling KK, Renninger NS, Newman JD (2013) High-level semi-synthetic production of the potent antimalarial artemisinin. Nature 496:528–532
Schrader J, Bohlmann J (2015) Biotechnology of isoprenoids. Advances in biochemical engineering/biotechnology, vol 148. Springer International Publishing
Brennan TCR, Turner CD, Krömer JO, Nielsen LK (2012) Alleviating monoterpene toxicity using a two-phase extractive fermentation for the bioproduction of jet fuel mixtures in Saccharomyces cerevisiae. Biotechnol Bioeng 109:2513–2522
Alonso-Gutierrez J, Chan R, Batth TS, Adams PD, Keasling JD, Petzold CJ, Lee TS (2013) Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. Metab Eng 19:33–41
Frohwitter J, Heider SA, Peters-Wendisch P, Beekwilder J, Wendisch VF (2014) Production of the sesquiterpene (+)-valencene by metabolically engineered Corynebacterium glutamicum. J Biotechnol 191:205–213
Wriessnegger T, Augustin P, Engleder M, Leitner E, Muller M, Kaluzna I, Schurmann M, Mink D, Zellnig G, Schwab H, Pichler H (2014) Production of the sesquiterpenoid (+)-nootkatone by metabolic engineering of Pichia pastoris. Metab Eng 24:18–29
Li N, Chang WC, Warui DM, Booker SJ, Krebs C, Bollinger JM (2012) Evidence for only oxygenative cleavage of aldehydes to alk(a/e)nes and formate by cyanobacterial aldehyde decarbonylases. Biochemistry 51:7908–7916
Warui DM, Li N, Norgaard H, Krebs C, Bollinger JM, Booker SJ (2011) Detection of formate, rather than carbon monoxide, as the stoichiometric coproduct in conversion of fatty aldehydes to alkanes by a cyanobacterial aldehyde decarbonylase. J Am Chem Soc 133:3316–3319
DomÃnguez de MarÃa P (2011) Recent developments in the biotechnological production of hydrocarbons: paving the way for bio-based platform chemicals. ChemSusChem 4:327–329
Harger M, Zheng L, Moon A, Ager C, An JH, Choe C, Lai Y-L, Mo B, Zong D, Smith MD, Egbert RG, Mills JH, Baker D, Pultz IS, Siegel JB (2013) Expanding the product profile of a microbial alkane biosynthetic pathway. ACS Synth Biol 2:59–62
Howard TP, Middelhaufe S, Moore K, Edner C, Kolak DM, Taylor GN, Parker DA, Lee R, Smirnoff N, Aves SJ, Love J (2013) Synthesis of customized petroleum-replica fuel molecules by targeted modification of free fatty acid pools in Escherichia coli. Proc Natl Acad Sci 110:7636–7641
Schneider-Belhaddad F, Kolattukudy P (2000) Solubilization, partial purification, and characterization of a fatty aldehyde decarbonylase from a higher plant, Pisum sativum. Arch Biochem Biophys 377:341–349
Choi YJ, Lee SY (2013) Microbial production of short-chain alkanes. Nature 502:571–574
Zachos I, Gassmeyer SK, Bauer D, Sieber V, Hollmann F, Kourist R (2015) Photobiocatalytic decarboxylation for olefin synthesis. Chem Commun (Cambridge, England) 51:1918–1921
Beller HR, Goh EB, Keasling JD (2010) Genes involved in long-chain alkene biosynthesis in micrococcus luteus. Appl Environ Microbiol 76:1212–1223
Frias JA, Richman JE, Erickson JS, Wackett LP (2011) Purification and characterization of OleA from Xanthomonas campestris and demonstration of a non-decarboxylative Claisen condensation reaction. J Biol Chem 286:10930–10938
McKenna R, Moya L, McDaniel M, Nielsen DR (2015) Comparing in situ removal strategies for improving styrene bioproduction. Bioprocess Biosyst Eng 38:165–174
McKenna R, Thompson B, Pugh S, Nielsen DR (2014) Rational and combinatorial approaches to engineering styrene production by Saccharomyces cerevisiae. Microb Cell Factories 13
Claypool JT, Raman DR, Jarboe LR, Nielsen DR (2014) Technoeconomic evaluation of bio-based styrene production by engineered Escherichia coli. J Ind Microbiol Biotechnol 41:1211–1216
Azeem M, Borg-Karlson AK, Rajarao GK (2013) Sustainable bio-production of styrene from forest waste. Bioresour Technol 144:684–688
Fischer-Romero C, Tindall BJ, Jüttner F (1996) Tolumonas auensis gen. nov., sp. nov., a toluene-producing bacterium from anoxic sediments of a freshwater lake. Int J Syst Bacteriol 46:183–188
Heider J, Spormann AM, Beller HR, Widdel F (1998) Anaerobic bacterial metabolism of hydrocarbons. FEMS Microbiol Rev 22:459–473
Chen J, Henderson G, Grimm CC, Lloyd SW, Laine RA (1998) Termites fumigate their nests with naphthalene. Nature 392:558–559
Daisy BH, Strobel GA, Castillo U, Ezra D, Sears J, Weaver DK, Runyon JB (2002) Naphthalene, an insect repellent, is produced by Muscodor vitigenus, a novel endophytic fungus. Microbiology 148:3737–3741
Ahamed A, Ahring BK (2011) Production of hydrocarbon compounds by endophytic fungi Gliocladium species grown on cellulose. Bioresour Technol 102:9718–9722
Bäck J, Aaltonen H, Hellen H, Kajos MK, Patokoski J, Taipale R, Pumpanen J, Heinonsalo J (2010) Variable emissions of microbial volatile organic compounds (MVOCs) from root-associated fungi isolated from Scots pine. Atmos Environ 44:3651–3659
Heiden AC, Kobel K, Komenda M, Koppmann R, Shao M, Wildt J (1999) Toluene emissions from plants. Geophys Res Lett 26:1283–1286
Strobel GA (2015) Bioprospecting-fuels from fungi. Biotechnol Lett 37:973–982
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
Straathof, A.J.J., Cuellar, M.C. (2017). Microbial Hydrocarbon Formation from Biomass. In: Wagemann, K., Tippkötter, N. (eds) Biorefineries. Advances in Biochemical Engineering/Biotechnology, vol 166. Springer, Cham. https://doi.org/10.1007/10_2016_62
Download citation
DOI: https://doi.org/10.1007/10_2016_62
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-97117-9
Online ISBN: 978-3-319-97119-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)