Engineering Escherichia coli for Conversion of Glucose to Medium-Chain ω-Hydroxy Fatty Acids and α,ω-Dicarboxylic Acids

ACS Synthetic Biology

Volumn 5, Issue 3, 2016, Pages 200-206

  Bowen, Christopher H ^a   Bonin, Jeff ^a   Kogler, Anna ^a   Barba Ostria, Carlos ^a   Zhang, Fuzhong ^a,b,c  

^a WASHINGTON UNIVERSITY IN ST LOUIS   (United States)

^b Division of Biological and Biomedical Sciences   (United States)

^c WASHINGTON UNIVERSITY   (United States)

Author keywords

alcohol dehydrogenase; aldehyde dehydrogenase; biobased plastics; medium chain , dicarboxylic acids; medium chain hydroxy fatty acids; nylon 6,12

Indexed keywords

ALPHA OMEGA DICARBOXYLIC ACID; DICARBOXYLIC ACID; GLUCOSE; HYDROXY FATTY ACID; OMEGA HYDROXY FATTY ACID; UNCLASSIFIED DRUG; ALCOHOL DEHYDROGENASE; FATTY ACID;

ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; CONTROLLED STUDY; ESCHERICHIA COLI; FED BATCH FERMENTATION; GAS CHROMATOGRAPHY; GENE EXPRESSION; GLUCOSE METABOLISM; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS OLEOVORANS; BATCH CELL CULTURE; GENETIC ENGINEERING; GENETICS; MASS FRAGMENTOGRAPHY; METABOLISM; OXIDATION REDUCTION REACTION; PLASMID;

ALCOHOL DEHYDROGENASE; BATCH CELL CULTURE TECHNIQUES; DICARBOXYLIC ACIDS; ESCHERICHIA COLI; FATTY ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GENETIC ENGINEERING; GLUCOSE; OXIDATION-REDUCTION; PLASMIDS;

EID: 84961844661     PISSN: None     EISSN: 21615063     Source Type: Journal    
DOI: 10.1021/acssynbio.5b00201     Document Type: Article

References (30)

1. IE Association. ((2013) Technology Roadmap Energy and GHG Reductions in the Chemical Industry via Catalytic Processes, IEA, Paris.
2. Chung, H., Yang, J. E., Ha, J. Y., Chae, T. U., Shin, J. H., Gustavsson, M., and Lee, S. Y. (2015) Bio-based production of monomers and polymers by metabolically engineered microorganisms Curr. Opin. Biotechnol. 36, 73-84 10.1016/j.copbio.2015.07.003
3. Thompson, R., Swan, S., Moore, C., and vom Saal, F. (2009) Our plastic age Philos. Trans. R. Soc., B 364, 1973-1976 10.1098/rstb.2009.0054
4. Song, H. and Lee, S. Y. (2006) Production of succinic acid by bacterial fermentation Enzyme Microb. Technol. 39, 352-361 10.1016/j.enzmictec.2005.11.043
5. Shin, J. H. and Lee, S. Y. (2014) Metabolic engineering of microorganisms for the production of L-arginine and its derivatives Microb. Cell Fact. 13, 166 10.1186/s12934-014-0166-4
6. Yu, J. L., Xia, X. X., Zhong, J. J., and Qian, Z. G. (2014) Direct biosynthesis of adipic acid from a synthetic pathway in recombinant Escherichia coli Biotechnol. Bioeng. 111, 2580-2586 10.1002/bit.25293
7. Clomburg, J. M., Blankschien, M. D., Vick, J. E., Chou, A., Kim, S., and Gonzalez, R. (2015) Integrated engineering of beta-oxidation reversal and omega-oxidation pathways for the synthesis of medium chain omega-functionalized carboxylic acids Metab. Eng. 28, 202-212 10.1016/j.ymben.2015.01.007
8. Honda Malca, S., Scheps, D., Kuhnel, L., Venegas-Venegas, E., Seifert, A., Nestl, B. M., and Hauer, B. (2012) Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids Chem. Commun. 48, 5115-5117 10.1039/c2cc18103g
9. Liu, C., Liu, F., Cai, J., Xie, W., Long, T. E., Turner, S. R., Lyons, A., and Gross, R. A. (2011) Polymers from fatty acids: poly(omega-hydroxyl tetradecanoic acid) synthesis and physico-mechanical studies Biomacromolecules 12, 3291-3298 10.1021/bm2007554
10. Scheps, D., Honda Malca, S., Richter, S. M., Marisch, K., Nestl, B. M., and Hauer, B. (2013) Synthesis of omega-hydroxy dodecanoic acid based on an engineered CYP153A fusion construct Microb. Biotechnol. 6, 694-707 10.1111/1751-7915.12073
11. Lu, W., Ness, J. E., Xie, W., Zhang, X., Minshull, J., and Gross, R. A. (2010) Biosynthesis of monomers for plastics from renewable oils J. Am. Chem. Soc. 132, 15451-15455 10.1021/ja107707v
12. Picataggio, S., Rohrer, T., Deanda, K., Lanning, D., Reynolds, R., Mielenz, J., and Eirich, L. D. (1992) Metabolic engineering of Candida tropicalis for the production of long-chain dicarboxylic acids Bio/Technology 10, 894-898 10.1038/nbt0892-894
13. Song, J. W., Jeon, E. Y., Song, D. H., Jang, H. Y., Bornscheuer, U. T., Oh, D. K., and Park, J. B. (2013) Multistep enzymatic synthesis of long-chain alpha,omega-dicarboxylic and omega-hydroxycarboxylic acids from renewable fatty acids and plant oils Angew. Chem., Int. Ed. 52, 2534-2537 10.1002/anie.201209187
14. Song, J., Lee, J., Bornscheuer, U. T., and Park, J. B. (2014) Microbial synthesis of medium-chain dicarboxylic acids and aminocarboxylic acids from renewable long-chain fatty acids Adv. Synth. Catal. 356, 1782-1788 10.1002/adsc.201300784
15. Pfleger, B. F., Gossing, M., and Nielsen, J. (2015) Metabolic engineering strategies for microbial synthesis of oleochemicals Metab. Eng. 29, 1-11 10.1016/j.ymben.2015.01.009
16. Xu, P., Gu, Q., Wang, W., Wong, L., Bower, A. G., Collins, C. H., and Koffas, M. A. (2013) Modular optimization of multi-gene pathways for fatty acids production in E. coli Nat. Commun. 4, 1409 10.1038/ncomms2425
17. Zhang, F., Ouellet, M., Batth, T. S., Adams, P. D., Petzold, C. J., Mukhopadhyay, A., and Keasling, J. D. (2012) Enhancing fatty acid production by the expression of the regulatory transcription factor FadR Metab. Eng. 14, 653-660 10.1016/j.ymben.2012.08.009
18. Lee, T. S., Krupa, R. A., Zhang, F., Hajimorad, M., Holtz, W. J., Prasad, N., Lee, S. K., and Keasling, J. D. (2011) BglBrick vectors and datasheets: A synthetic biology platform for gene expression J. Biol. Eng. 5, 12 10.1186/1754-1611-5-12
19. Altschul, S. F., Madden, T. L., Schaffer, A. A., Zhang, J., Zhang, Z., Miller, W., and Lipman, D. J. (1997) Gapped BLAST and PSI-BLAST: a new generation of protein database search programs Nucleic Acids Res. 25, 3389-3402 10.1093/nar/25.17.3389
20. Jo, J. E., Mohan Raj, S., Rathnasingh, C., Selvakumar, E., Jung, W. C., and Park, S. (2008) Cloning, expression, and characterization of an aldehyde dehydrogenase from Escherichia coli K-12 that utilizes 3-Hydroxypropionaldehyde as a substrate Appl. Microbiol. Biotechnol. 81, 51-60 10.1007/s00253-008-1608-x
21. Eirich, L. D., Craft, D. L., Steinberg, L., Asif, A., Eschenfeldt, W. H., Stols, L., Donnelly, M. I., and Wilson, C. R. (2004) Cloning and characterization of three fatty alcohol oxidase genes from Candida tropicalis strain ATCC 20336 Applied and environmental microbiology 70, 4872-4879 10.1128/AEM.70.8.4872-4879.2004
22. Benson, S. and Shapiro, J. (1976) Plasmid-determined alcohol dehydrogenase activity in alkane-utilizing strains of Pseudomonas putida J. Bacteriol. 126, 794-798
23. van Beilen, J. B., Eggink, G., Enequist, H., Bos, R., and Witholt, B. (1992) DNA sequence determination and functional characterization of the OCT-plasmid-encoded alkJKL genes of Pseudomonas oleovorans Mol. Microbiol. 6, 3121-3136 10.1111/j.1365-2958.1992.tb01769.x
24. Kirmair, L. and Skerra, A. (2014) Biochemical analysis of recombinant AlkJ from Pseudomonas putida reveals a membrane-associated, flavin adenine dinucleotide-dependent dehydrogenase suitable for the biosynthetic production of aliphatic aldehydes Applied and environmental microbiology 80, 2468-2477 10.1128/AEM.04297-13
25. Schrewe, M., Julsing, M. K., Lange, K., Czarnotta, E., Schmid, A., and Buhler, B. (2014) Reaction and catalyst engineering to exploit kinetically controlled whole-cell multistep biocatalysis for terminal FAME oxyfunctionalization Biotechnol. Bioeng. 111, 1820-1830 10.1002/bit.25248
26. He, L., Xiao, Y., Gebreselassie, N., Zhang, F., Antoniewiez, M. R., Tang, Y. J., and Peng, L. (2014) Central metabolic responses to the overproduction of fatty acids in Escherichia coli based on 13C-metabolic flux analysis Biotechnol. Bioeng. 111, 575-585 10.1002/bit.25124
27. Karuzina, II and Archakov, A. I. (1994) Hydrogen peroxide-mediated inactivation of microsomal cytochrome P450 during monooxygenase reactions Free Radical Biol. Med. 17, 557-567 10.1016/0891-5849(94)90095-7
28. Anderson, J. C., Dueber, J. E., Leguia, M., Wu, G. C., Goler, J. A., Arkin, A. P., and Keasling, J. D. (2010) BglBricks: A flexible standard for biological part assembly J. Biol. Eng. 4, 1 10.1186/1754-1611-4-1
29. Jiang, W., Jiang, Y., Bentley, G. J., Liu, D., Xiao, Y., and Zhang, F. (2015) Enhanced production of branched-chain fatty acids by replacing beta-ketoacyl-(acyl-carrier-protein) synthase III (FabH) Biotechnol. Bioeng. 112, 1613-1622 10.1002/bit.25583
30. Liu, D., Xiao, Y., Evans, B., and Zhang, F. (2015) Negative feedback regulation of fatty acid production based on a malonyl-CoA sensor-actuator ACS Synth. Biol. 4, 132-140 10.1021/sb400158w