Renewable production of high density jet fuel precursor sesquiterpenes from Escherichia coli
Open accessAbstract
Aviation fuels are an important target of biofuels research due to their high market demand and competitive price. Isoprenoids have been demonstrated as good feedstocks for advanced renewable jet fuels with high energy density, high heat of combustion, and excellent cold-weather performance. In particular, sesquiterpene compounds (C 15 ), such as farnesene and bisabolene, have been identified as promising jet fuel candidates. In this study, we explored three sesquiterpenes—epi-isozizaene, pentalenene and α-isocomene—as novel jet fuel precursors. We performed a computational analysis to calculate the energy of combustion of these sesquiterpenes and found that their specific energies are comparable to commercial jet fuel A-1. Through heterologous MVA pathway expression and promoter engineering, we produced 727.9 mg/L epi-isozizaene, 780.3 mg/L pentalenene and 77.5 mg/L α-isocomene in Escherichia coli and 344 mg/L pentalenene in Saccharomyces cerevisiae . We also introduced a dynamic autoinduction system using previously identified FPP-responsive promoters for inducer-free production and managed to achieve comparable amounts of each compound. We produced tricyclic sesquiterpenes epi-isozizaene, pentalenene and α-isocomene, promising jet fuel feedstocks at high production titers, providing novel, sustainable alternatives to petroleum-based jet fuels.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Hydrogenation of β-farnesene produces farnesane which is an alkane which has displayed potential as a high energy density alternative fuel option.
“Hydrogenation of β-farnesene produces farnesane which is an alkane which has displayed potential as a high energy density alternative fuel option [139].”
From Investigation of Biofuel as a Potential Renewable Energy Source (2021) · cites this paper as [139]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
Enzymatic assembly of DNA molecules up to several hundred kilobases
Gibson, D. G., Young, L., Chuang, R.-Y., Venter, J. C., Hutchison, C. A., & Smith, H. O. (2009) · Nature Methods · doi:10.1038/nmeth.1318 · Cited by 9,742 · see citing works
Production of the antimalarial drug precursor artemisinic acid in engineered yeast
Ro, D.-K., Paradise, E. M., Ouellet, M., Fisher, K. J., Newman, K. L., Ndungu, J. M., Ho, K. A., Eachus, R. A., Ham, T. S., Kirby, J., et al. (2006) · Nature · doi:10.1038/nature04640 · Cited by 2,805 · see citing works
Self-citationRecombinant protein expression in Escherichia coli: advances and challenges
Rosano, G. L., & Ceccarelli, E. A. (2014) · Frontiers in Microbiology · doi:10.3389/fmicb.2014.00172 · Cited by 2,556 · see citing works
Handbook of Hydrocarbon and Lipid Microbiology
Timmis, K. N. (2009) · Springer eBooks · doi:10.1007/978-3-540-77587-4 · Cited by 1,959 · see citing works
Engineering a mevalonate pathway in Escherichia coli for production of terpenoids
Martin, V. J. J., Pitera, D. J., Withers, S. T., Newman, J. D., & Keasling, J. D. (2003) · Nature Biotechnology · doi:10.1038/nbt833 · Cited by 1,720 · see citing works
Self-citationIdentification and microbial production of a terpene-based advanced biofuel
Peralta‐Yahya, P., Ouellet, M., Chan, R., Mukhopadhyay, A., Keasling, J. D., & Lee, T. S. (2011) · Nature Communications · doi:10.1038/ncomms1494 · Cited by 638 · see citing works
Self-citationLee, S. K., Chou, H., Ham, T. S., Lee, T. S., & Keasling, J. D. (2008) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2008.10.014 · Cited by 616 · see citing works
Self-citationEngineering dynamic pathway regulation using stress-response promoters
Dahl, R. H., Zhang, F., Alonso-Gutiérrez, J., Baidoo, E. E. K., Batth, T. S., Redding‐Johanson, A. M., Petzold, C. J., Mukhopadhyay, A., Lee, T. S., Adams, P. D., et al. (2013) · Nature Biotechnology · doi:10.1038/nbt.2689 · Cited by 477 · see citing works
Self-citationSeparations of lipids by silver ion chromatography
Morris, L. J. (1966) · Journal of Lipid Research · doi:10.1016/s0022-2275(20)38948-3 · Cited by 444 · see citing works
Metabolic engineering of microbial pathways for advanced biofuels production
Zhang, F., Rodriguez, S., & Keasling, J. D. (2011) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2011.04.024 · Cited by 350 · see citing works
Self-citationHigh-Density Renewable Fuels Based on the Selective Dimerization of Pinenes
Harvey, B. G., Wright, M. E., & Quintana, R. L. (2009) · Energy & Fuels · doi:10.1021/ef900799c · Cited by 291 · see citing works
The compatibility of potential bioderived fuels with Jet A-1 aviation kerosene
Chuck, C. J., & Donnelly, J. (2014) · Applied Energy · doi:10.1016/j.apenergy.2013.12.019 · Cited by 281 · see citing works
Metabolic engineering of Escherichia coli for α-farnesene production
Wang, C., Yoon, S., Jang, H., Chung, Y., Kim, J., Choi, E., & Kim, S.-W. (2011) · Metabolic Engineering · doi:10.1016/j.ymben.2011.08.001 · Cited by 208 · see citing works
Zhu, F., Zhong, X., Hu, M., Lü, L., Deng, Z., & Liu, T. (2014) · Biotechnology and Bioengineering · doi:10.1002/bit.25198 · Cited by 203 · see citing works
Microbial production of advanced transportation fuels in non-natural hosts
Connor, M. R., & Liao, J. C. (2009) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2009.04.002 · Cited by 193 · see citing works
Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus
Agger, S. A., López‐Gallego, F., & Schmidt‐Dannert, C. (2009) · Molecular Microbiology · doi:10.1111/j.1365-2958.2009.06717.x · Cited by 192 · see citing works
Isoprenoid drugs, biofuels, and Chemicals–Artemisinin, farnesene, and beyond
George, K. W., Alonso-Gutierrez, J., Keasling, J. D., & Lee, T. S. (2015) · Advances in biochemical engineering, biotechnology · doi:10.1007/10_2014_288 · Cited by 185 · see citing works
Self-citationBiosynthesis of the Sesquiterpene Antibiotic Albaflavenone in Streptomyces coelicolor A3(2)
Zhao, B., Lin, X., Li, L., Lamb, D. C., Kelly, S. L., Waterman, M. R., & Cane, D. E. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m710421200 · Cited by 185 · see citing works
Targeted proteomics for metabolic pathway optimization: Application to terpene production
Redding‐Johanson, A. M., Batth, T. S., Chan, R., Krupa, R. A., Szmidt, H. L., Adams, P. D., Keasling, J. D., Lee, T. S., Mukhopadhyay, A., & Petzold, C. J. (2011) · Metabolic Engineering · doi:10.1016/j.ymben.2010.12.005 · Cited by 179 · see citing works
Self-citationPentalenene Synthase. Analysis of Active Site Residues by Site-Directed Mutagenesis
Seemann, M., Zhai, G., de Kraker, J., et al. (2002) · Journal of the American Chemical Society · doi:10.1021/ja026058q · Cited by 168 · see citing works
Himmelberger, J. A., Lin, X., Cane, D. E., et al. (2010) · Biochemistry · doi:10.1021/bi902088z · Cited by 158 · see citing works
Lin, X., Hopson, R., & Cane, D. E. (2006) · Journal of the American Chemical Society · doi:10.1021/ja061292s · Cited by 156 · see citing works
Natural products as biofuels and bio-based chemicals: fatty acids and isoprenoids
Beller, H. R., Lee, T. S., & Katz, L. (2015) · Natural Product Reports · doi:10.1039/c5np00068h · Cited by 153 · see citing works
Self-citationCane, D. E., Sohng, J.-K., Lamberson, C. R., et al. (1994) · Biochemistry · doi:10.1021/bi00185a024 · Cited by 150 · see citing works
Heterologous production of α-farnesene in metabolically engineered strains of Yarrowia lipolytica
Yang, X., Nambou, K., Wei, L., et al. (2016) · Bioresource Technology · doi:10.1016/j.biortech.2016.06.028 · Cited by 148 · see citing works
Technoeconomic analysis of renewable aviation fuel from microalgae, Pongamia pinnata, and sugarcane
Klein‐Marcuschamer, D., Turner, C., Allen, M., Gray, P. P., Dietzgen, R. G., Gresshoff, P. M., Hankamer, B. D., Heimann, K., Scott, P. T., Stephens, E., et al. (2013) · Biofuels Bioproducts and Biorefining · doi:10.1002/bbb.1404 · Cited by 146 · see citing works
Fatty acid alkyl esters: perspectives for production of alternative biofuels
Röttig, A., Wenning, L., Bröker, D., & Steinbüchel, A. (2009) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-009-2383-z · Cited by 144 · see citing works
Qu, R., Liu, H., Feng, M., et al. (2012) · Journal of Chemical & Engineering Data · doi:10.1021/je300407g · Cited by 112 · see citing works
Production of jet fuel precursor monoterpenoids from engineered Escherichia coli
Mendez‐Perez, D., Alonso-Gutiérrez, J., Hu, Q., et al. (2017) · Biotechnology and Bioengineering · doi:10.1002/bit.26296 · Cited by 101 · see citing works
The in vivo synthesis of plant sesquiterpenes by Escherichia coli
Martin, V. J. J., Yoshikuni, Y., & Keasling, J. D. (2001) · Biotechnology and Bioengineering · doi:10.1002/bit.10037 · Cited by 99 · see citing works
Self-citationMetabolic engineering of microorganisms for isoprenoid production
Kirby, J., & Keasling, J. D. (2008) · Natural Product Reports · doi:10.1039/b802939c · Cited by 91 · see citing works
Self-citationIrmisch, S., Krause, S. T., Kunert, G., Gershenzon, J., Degenhardt, J., & Köllner, T. G. (2012) · BMC Plant Biology · doi:10.1186/1471-2229-12-84 · Cited by 87 · see citing works
Harvey, B. G., Meylemans, H. A., Gough, R. V., Quintana, R. L., Garrison, M. D., & Bruno, T. J. (2014) · Physical Chemistry Chemical Physics · doi:10.1039/c3cp55349c · Cited by 83 · see citing works
Li, R., Chou, W. K. W., Himmelberger, J. A., et al. (2014) · Biochemistry · doi:10.1021/bi401643u · Cited by 75 · see citing works
Renewable high density fuels containing tricyclic sesquiterpanes and alkyl diamondoids
Harrison, K. W., & Harvey, B. G. (2017) · Sustainable Energy & Fuels · doi:10.1039/c6se00108d · Cited by 69 · see citing works
Takamatsu, S., Lin, X., Nara, A., et al. (2010) · Microbial Biotechnology · doi:10.1111/j.1751-7915.2010.00209.x · Cited by 66 · see citing works
Evolutionary Engineering Improves Tolerance for Replacement Jet Fuels in Saccharomyces cerevisiae
Brennan, T. C. R., Williams, T. C., Schulz, B. L., Palfreyman, R. W., Krömer, J. O., & Nielsen, L. K. (2015) · Applied and Environmental Microbiology · doi:10.1128/aem.04144-14 · Cited by 63 · see citing works
Thermodynamic and Ab Initio Analysis of the Controversial Enthalpy of Formation of Formaldehyde
da Silva, G. F., Bozzelli, J. W., Sebbar, N., & Bockhorn, H. (2006) · ChemPhysChem · doi:10.1002/cphc.200500667 · Cited by 54 · see citing works
Isoprenoid-Based Biofuels: Homologous Expression and Heterologous Expression in Prokaryotes
Phulara, S. C., Chaturvedi, P., & Gupta, P. (2016) · Applied and Environmental Microbiology · doi:10.1128/aem.01192-16 · Cited by 49 · see citing works
Total synthesis of (.+-.)-isocomene, a naturally occurring triquinane
Paquette, L. A., & Han, Y.-K. (1981) · Journal of the American Chemical Society · doi:10.1021/ja00397a044 · Cited by 43 · see citing works
Formal total synthesis of (.+-.)-isocomene
Dauben, W. G., & Walker, D. M. (1981) · The Journal of Organic Chemistry · doi:10.1021/jo00319a013 · Cited by 40 · see citing works
Hong, Y. J., Irmisch, S., Wang, S. C., et al. (2013) · Chemistry - A European Journal · doi:10.1002/chem.201301018 · Cited by 34 · see citing works
Self-citationAn asymmetric total synthesis of (+)-pentalenene
Kim, Y.-J., Yoon, Y., & Lee, H. (2013) · Tetrahedron · doi:10.1016/j.tet.2013.05.095 · Cited by 20 · see citing works
A Computational Study of the Ozonolysis of Phenanthrene
Almatarneh, M. H., AlShamaileh, E. M., Ahmad, Z. M., et al. (2017) · Acta Physica Polonica A · doi:10.12693/aphyspola.132.1149 · Cited by 12 · see citing works
Dual Action Additives for Jet A-1: Fuel Dehydrating Icing Inhibitors
Repetto, S. L., Patel, R., Johnson, T., et al. (2016) · Energy & Fuels · doi:10.1021/acs.energyfuels.6b01727 · Cited by 9 · see citing works
Advanced Biodiesel and Biojet Fuels from Lignocellulosic Biomass
Tian, T., & Lee, T. S. (2017) · Springer eBooks · doi:10.1007/978-3-319-50436-0_372 · Cited by 5 · see citing works
Self-citation
Flagged first, then by citations
Cited by
Sorted by citations
Investigation of Biofuel as a Potential Renewable Energy Source
Khan, M. A. H., Bonifacio, S., Clowes, J., Foulds, A., Holland, R., Matthews, J. C., Percival, C. J., & Shallcross, D. E. (2021) · Atmosphere · doi:10.3390/atmos12101289 · Cited by 140 · see citing works
- Authors
- Liu, C.-L., Tian, T., Alonso-Gutierrez, J., Garabedian, B., Wang, S., Baidoo, E. E. K., Benites, V., Chen, Y., Petzold, C. J., Adams, P. D., Keasling, J. D., Tan, T., & Lee, T. S.
- Affiliations
- Lawrence Berkeley National Laboratory (US)
- Beijing University of Chemical Technology (CN)
- Corresponding author
- Tan, Tianwei
- Lee, Taek Soon
- ORCID
- Venue
- Biotechnology for Biofuels
- Published
- 2018-10-20
- Volume
- 11
- Issue
- 1
- Pages
- 285-285
- ISSN
- 1754-6834 (ISSN-L)
- PMC
- PMC6195743
- OpenAlex
- W2897769271
- Cited by
- 70
- References
- 46
- Citations by year
- 2026: 4 · 2025: 10 · 2024: 12 · 2023: 11 · 2022: 11 · 2021: 11 · 2020: 8 · 2019: 3
- FWCI
- 1.96
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Biotechnology for Biofuels (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- eScholarship (California Digital Library) (submittedVersion, other-oa)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
- eScholarship (California Digital Library) (submittedVersion)
- OSTI OAI (U.S. Department of Energy Office of Scientific and Technical Information) (submittedVersion)
- Technical University of Denmark, DTU Orbit (Technical University of Denmark, DTU) (submittedVersion, cc-by)
- Funders
- Office of Science (DE-AC02-05CH11231)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Microbial Metabolic Engineering and Bioproduction
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Biochemical and biochemical processes
- Keywords
- renewable jet fuel, sesquiterpenes, pentalenene, terpenoids, Escherichia coli, Saccharomyces cerevisiae, promoter engineering, autoinduction, aviation biofuels
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review