Selective production of decanoic acid from iterative reversal of β-oxidation pathway

Biotechnology and Bioengineering

Volumn 115, Issue 5, 2018, Pages 1311-1320

  Kim, Seohyoung ^a   Gonzalez, Ramon ^a  

^a Rice University   (United States)

Author keywords

carbon elongation; decanoic acid; fatty acids; metabolic engineering; reversal oxidation

Indexed keywords

CHAINS; CYTOLOGY; ENZYME ACTIVITY; ESCHERICHIA COLI; FATTY ACIDS; GLYCEROL; INDUSTRIAL CHEMICALS; METABOLIC ENGINEERING; OXIDATION;

BETA OXIDATION; CONCENTRATION GRADIENTS; DECANOIC ACID; ENGINEERED STRAINS; EXTRACELLULAR MEDIUM; INTRACELLULAR ACCUMULATION; RENEWABLE FEEDSTOCKS; SELECTIVE PRODUCTION;

SATURATED FATTY ACIDS;

ACETYL COENZYME A ACETYLTRANSFERASE; ACYL COENZYME A; DECANOIC ACID; ENOYL COENZYME A HYDRATASE; GLYCEROL; THIOL ESTER HYDROLASE; ANTIFUNGAL AGENT; DECANOIC ACID DERIVATIVE; RECOMBINANT PROTEIN;

ARTICLE; CELL MEMBRANE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENZYME SPECIFICITY; ENZYME SYNTHESIS; FATTY ACID OXIDATION; NONHUMAN; PROTEIN EXPRESSION; BIOTRANSFORMATION; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; METABOLIC ENGINEERING; METABOLISM; OXIDATION REDUCTION REACTION; PROCEDURES;

ANTIFUNGAL AGENTS; BIOTRANSFORMATION; DECANOIC ACIDS; ESCHERICHIA COLI; GENE EXPRESSION; GLYCEROL; METABOLIC ENGINEERING; METABOLIC NETWORKS AND PATHWAYS; OXIDATION-REDUCTION; RECOMBINANT PROTEINS;

EID: 85041559305     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.26540     Document Type: Article

References (40)

1. Atsumi, S., Cann, A. F., Connor, M. R., Shen, C. R., Smith, K. M., Brynildsen, M. P., … Liao, J. C. (2008). Metabolic engineering of Escherichia coli for 1-butanol production. Metabolic Engineering, 10, 305–311.
2. Bond-Watts, B. B., Weeks, A. M., & Chang, M. C. Y. (2012). Biochemical and structural characterization of the trans-enoyl-coa reductase from Treponema denticola. Biochemistry, 51, 6827–6837.
3. Carpenter, C. E., & Broadbent, J. R. (2009). External concentration of organic acid anions and pH: Key independent variables for studying how organic acids inhibit growth of bacteria in mildly acidic foods. Journal of Food Science, 74, 12–15.
4. Cheng, A. S. E., Dumitrescu, C. E., & Mueller, C. J. (2014). Investigation of methyl decanoate combustion in an optical direct-injection diesel engine. Energy & Fuels, 28, 7689–7700.
5. Cheong, S., Clomburg, J. M., & Gonzalez, R. (2016). Energy- and carbon-efficient synthesis of functionalized small molecules in bacteria using non-decarboxylative Claisen condensation reactions. Nature Biotechnology, 34, 556–561.
6. Clomburg, J. M., Blankschien, M. D., Vick, J. E., Chou, A., Kim, S., & Gonzalez, R. (2015). Integrated engineering of β-oxidation reversal and ω-oxidation pathways for the synthesis of medium chain ω-functionalized carboxylic acids. Metabolic Engineering, 28, 202–212.
7. Clomburg, J. M., Vick, J. E., Blankschien, M. D., Rodríguez-moya, M., & Gonzalez, R. (2012). A synthetic biology approach to engineer a functional reversal of the β-oxidation cycle. ACS Synthetic Biology, 1, 541–554.
8. Davis, M. S., Solbiati, J., & Cronan, J. E. (2000). Overproduction of acetyl-CoA carboxylase activity increases the rate of fatty acid biosynthesis in Escherichia coli. The Journal of Biological Chemistry, 275, 28593–28598.
9. Dehesh, K., Edwards, P., Hayes, T., Cranmer, A. M., & Fillatti, J. (1996a). Two novel thioesterases are key determinants of the bimodal distribution of acyl chain length of Cuphea palustvis seed oil. Plant Physiology, 110, 203–210.
10. Dehesh, K., Jones, A., Knutzon, D. S., & Voelker, T. A. (1996). Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana. The Plant Journal, 9, 167–172.
11. Dellomonaco, C., Clomburg, J. M., Miller, E. N., & Gonzalez, R. (2011). Engineered reversal of the β-oxidation cycle for the synthesis of fuels and chemicals. Nature, 476, 355–359.
12. Feng, Y., & Cronan, J. E. (2009). Escherichia coli unsaturated fatty acid synthesis. The Journal of Biochemistry, 284, 29526–29535.
13. Gajewski, J., Pavlovic, R., Fischer, M., Boles, E., & Grininger, M. (2017). Engineering fungal de novo fatty acid synthesis for short chain fatty acid production. Nature Communications, 8, 1–8.
14. Haynes, W. M. (2017). CRC handbook of chemistry and physics. CRC Handbook. Chemical Physics.
15. Heath, R., & Rock, C. (1996). Regulation of fatty acid elongation and initiation by acyl-acyl carrier protein in Escherichia coli. The Journal of Biological Chemistry, 271, 1833–1836.
16. Hoffmeister, M., Piotrowski, M., Nowitzki, U., & Martin, W. (2005). Mitochondrial trans-2-enoyl-CoA reductase of wax ester fermentation from Euglena gracilis defines a new family of enzymes involved in lipid synthesis. The Journal of Biological Chemistry, 280, 4329–4338.
17. Jackowski, S., & Rock, C. O. (1987). Acetoacetyl-acyl carrier protein synthase, a potential regulator of fatty acid biosynthesis in bacteria. The Journal of Biological Chemistry, 262, 7927–7931.
18. Janßen, H. J., & Steinbüchel, A. (2014). Fatty acid synthesis in Escherichia coli and its applications towards the production of fatty acid based biofuels. Biotechnol Biofuels, 7, 7.
19. Kim, S., Cheong, S., & Gonzalez, R. (2016). Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids. Metabolic Engineering, 36, 90–98.
20. Kim, S., Clomburg, J. M., & Gonzalez, R. (2015). Synthesis of medium-chain length (C6-C10) fuels and chemicals via β-oxidation reversal in Escherichia coli. Journal of Industrial Microbiology & Biotechnology, 42, 465–475.
21. Knothe, G. (2009). Improving biodiesel fuel properties by modifying fatty ester composition. Energy Environmental Science, 2, 759–766.
22. Knothe, G. (2008). “Designer” biodiesel: Optimizing fatty ester composition to improve fuel properties. Energy & Fuels, 22, 1358–1364.
23. Kubitschke J, Lange H, & Strutz H. 2014. Carboxylic Acids, Aliphatic. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH.
24. Lennen, R. M., & Pfleger, B. F. (2012). Engineering Escherichia coli to synthesize free fatty acids. Trends in Biotechnology, 30, 659–667.
25. Liu, H., Yu, C., Feng, D., Cheng, T., Meng, X., Liu, W., … Xian, M. (2012). Production of extracellular fatty acid using engineered Escherichia coli. Microbial Cell Factories, 11, 41.
26. Liu, X., Sheng, J., & Curtiss, R., III (2011). Fatty acid production in genetically modified cyanobacteria. Proceedings of the National Academy of Sciences of the United States of America, 108, 6899–6904.
27. Maloy, S. R., Ginsburgh, C. L., Simons, R. W., & Nunn, W. D. (1981). Transport of long and medium chain fatty acids by Escherichia coliK12. Journal of Biochemistry, 256, 3735–3742.
28. Nie, L., Ren, Y., & Schulz, H. (2008). Identification and characterization of Escherichia coli thioesterase III that functions in fatty acid oxidation. Biochemistry, 47, 7744–7751.
29. Ohlrogge, J. B. (1994). Design of new plant Products: Engineering of fatty acid metabolism. Plant Physiology, 104, 821–826.
30. Peralta-Yahya, P. P., Zhang, F., del Cardayre, S. B., & Keasling, J. D. (2012). Microbial engineering for the production of advanced biofuels. Nature, 488, 320–328.
31. Rodriguez, G. M., Tashiro, Y., & Atsumi, S. (2014). Expanding ester biosynthesis in Escherichia coli. Nature Chemical Biology, 10, 259–265.
32. Royce, L. A., Liu, P., Stebbins, M. J., Hanson, B. C., & Jarboe, L. R. (2013). The damaging effects of short chain fatty acids on Escherichia coli membranes. Applied Microbiology and Biotechnology, 97, 8317–8327.
33. Royce, L. A., Yoon, J. M., Chen, Y., Rickenbach, E., Shanks, J. V., & Jarboe, L. R. (2015). Evolution for exogenous octanoic acid tolerance improves carboxylic acid production and membrane integrity. Metabolic Engineering, 29, 180–188.
34. Slater, S., Houmiel, K. L., Tran, M., Timothy, A., Taylor, N. B., Padgette, S. R., … Gruys, K. J. (1998). Multiple β-ketothiolases mediate poly (β-hydroxyalkanoate) copolymer synthesis in Ralstonia eutropha. Journal of Bacteriology, 180, 1979–1987.
35. Steen, E. J., Kang, Y., Bokinsky, G., Hu, Z., Schirmer, A., McClure, A., … Keasling, J. D. (2010). Microbial production of fatty-acid-derived fuels and chemicals from plant biomass. Nature, 463, 559–562.
36. Vick, J. E., Clomburg, J. M., Blankschien, M. D., Chou, A., Kim, S., & Gonzalez, R. (2015). Escherichia coli enoyl-acyl carrier protein reductase (FabI) supports efficient operation of a functional reversal of the β-oxidation cycle. Applied and Environmental Microbiology, 81, 1406–1416.
37. Voelker, T. A., & Davies, H. M. (1994). Alteration of the specificity and regulation of alteration of the specificity and regulation of fatty acid synthesis of Escherichia coli by expression of a plant medium-chain acyl-acyl carrier protein Thioesterase. Journal of Bacteriology, 176, 7320–7327.
38. Waterson, R. M., Castellino, F. J., Hass, G. M., & Hill, R. L. (1972). Purification and characterization of crotonase from Clostridium acetobutylicum. Journal of Biochemistry, 247, 5266–5271.
39. Yu, A.-Q., Pratomo Juwono, N. K., Leong, S. S. J., & Chang, M. W. (2014). Production of fatty acid-derived valuable chemicals in synthetic microbes. Frontiers in Bioengineering and Biotechnology, 2, 78.
40. Zheng, Z., Gong, Q., Liu, T., Deng, Y., Chen, G., & Chen, J. (2004). Thioesterase II of Escherichia coli plays an important role in 3-hydroxydecanoic acid production. Applied and Environmental Microbiology, 27, 3807–3813.