Expanding ester biosynthesis in Escherichia coli

Nature Chemical Biology

Volumn 10, Issue 4, 2014, Pages 259-265

  Rodriguez, Gabriel M ^a   Tashiro, Yohei ^a   Atsumi, Shota ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 1 BUTYL ALCOHOL; 3 METHYL 1 BUTYL ALCOHOL; ACETIC ACID; ACYL COENZYME A; ALCOHOL; ALCOHOL DERIVATIVE; ESTER; GLUCOSE; ISOBUTANOL; ISOBUTYRIC ACID; PHENETHYL ALCOHOL; PROPANOL; UNCLASSIFIED DRUG;

ALCOHOL PRODUCTION; ARTICLE; BIOSYNTHESIS; ENZYME STRUCTURE; ENZYME SYNTHESIS; ESCHERICHIA COLI; NONHUMAN; PRIORITY JOURNAL;

ESCHERICHIA COLI;

3-METHYL-2-OXOBUTANOATE DEHYDROGENASE (LIPOAMIDE); ACETATES; BUTANOLS; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COENZYME A; ESCHERICHIA COLI; ESTERIFICATION; ESTERS; GLUCOSE; INDICATORS AND REAGENTS; PLASMIDS; PROTEINS; PSEUDOMONAS PUTIDA; SACCHAROMYCES CEREVISIAE; VIBRIO;

EID: 84897025067     PISSN: 15524450     EISSN: 15524469     Source Type: Journal    
DOI: 10.1038/nchembio.1476     Document Type: Article

References (46)

1. Beekwilder, J. et al. Functional characterization of enzymes forming volatile esters from strawberry and banana. Plant Physiol. 135, 1865-1878 (2004).
2. Verstrepen, K.J. et al. Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters. Appl. Environ. Microbiol. 69, 5228-5237 (2003).
3. Iwasaki, T., Maegawa, Y., Ohshima, T. & Mashima, K. in Kirk-Othmer Encyclopedia of Chemical Technology Vol. 10, 497-516 (John Wiley & Sons, New Jersey, 2012).
4. Liu, Y.J., Lotero, E. & Goodwin, J.G. Effect of water on sulfuric acid catalyzed esterification. J. Mol. Catal. Chem. 245, 132-140 (2006).
5. Nelson, D.L. & Cox, M.M. Lehninger Principles of Biochemistry 5th edn. (Sara Tenney, New York, 2008).
6. Stergiou, P.Y. et al. Advances in lipase-catalyzed esterification reactions. Biotechnol. Adv. 31, 1846-1859 (2013).
7. Dhake, K.P., Thakare, D.D. & Bhanage, B.M. Lipase: a potential biocatalyst for the synthesis of valuable flavour and fragrance ester compounds. Flavour Fragrance J. 28, 71-83 (2013).
8. Rabinovitch-Deere, C.A., Oliver, J.W., Rodriguez, G.M. & Atsumi, S. Synthetic biology and metabolic engineering approaches to produce biofuels. Chem. Rev. 113, 4611-4632 (2013).
9. Bornscheuer, U.T. et al. Engineering the third wave of biocatalysis. Nature 485, 185-194 (2012).
10. Fujii, T. et al. Molecular cloning, sequence analysis, and expression of the yeast alcohol acetyltransferase gene. Appl. Environ. Microbiol. 60, 2786-2792 (1994).
11. Rowland, O. & Domergue, F. Plant fatty acyl reductases: enzymes generating fatty alcohols for protective layers with potential for industrial applications. Plant Sci. 193-194, 28-38 (2012).
12. Rontani, J.F., Bonin, P.C. & Volkman, J.K. Production of wax esters during aerobic growth of marine bacteria on isoprenoid compounds. Appl. Environ. Microbiol. 65, 221-230 (1999).
13. Lenneman, E.M., Ohlert, J.M., Palani, N.P. & Barney, B.M. Fatty alcohols for wax esters in Marinobacter aquaeolei VT8: two optional routes in the wax biosynthesis pathway. Appl. Environ. Microbiol. 79, 7055-7062 (2013).
14. Reiser, S. & Somerville, C. Isolation of mutants of Acinetobacter calcoaceticus deficient in wax ester synthesis and complementation of one mutation with a gene encoding a fatty acyl coenzyme A reductase. J. Bacteriol. 179, 2969-2975 (1997).
15. Holtzapple, E. & Schmidt-Dannert, C. Biosynthesis of isoprenoid wax ester in Marinobacter hydrocarbonoclasticus DSM 8798: identification and characterization of isoprenoid coenzyme A synthetase and wax ester synthases. J. Bacteriol. 189, 3804-3812 (2007).
16. Barney, B.M., Wahlen, B.D., Garner, E., Wei, J. & Seefeldt, L.C. Differences in substrate specificities of five bacterial wax ester synthases. Appl. Environ. Microbiol. 78, 5734-5745 (2012).
17. Stöveken, T., Kalscheuer, R., Malkus, U., Reichelt, R. & Steinbuchel, A. The wax ester synthase/acyl coenzyme A:diacylglycerol acyltransferase from Acinetobacter sp. strain ADP1: characterization of a novel type of acyltransferase. J. Bacteriol. 187, 1369-1376 (2005).
18. Atsumi, S., Hanai, T. & Liao, J.C. Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels. Nature 451, 86-89 (2008).
19. Shen, C.R. et al. Driving forces enable high-titer anaerobic 1-butanol synthesis in Escherichia coli. Appl. Environ. Microbiol. 77, 2905-2915 (2011).
20. Bond-Watts, B.B., Bellerose, R.J. & Chang, M.C. Enzyme mechanism as a kinetic control element for designing synthetic biofuel pathways. Nat. Chem. Biol. 7, 222-227 (2011).
21. Inokuma, K., Liao, J.C., Okamoto, M. & Hanai, T. Improvement of isopropanol production by metabolically engineered Escherichia coli using gas stripping. J. Biosci. Bioeng. 110, 696-701 (2010).
22. Dellomonaco, C., Clomburg, J.M., Miller, E.N. & Gonzalez, R. Engineered reversal of the -oxidation cycle for the synthesis of fuels and chemicals. Nature 476, 355-359 (2011).
23. Saerens, S.M. et al. The Saccharomyces cerevisiae EHT1 and EEB1 genes encode novel enzymes with medium-chain fatty acid ethyl ester synthesis and hydrolysis capacity. J. Biol. Chem. 281, 4446-4456 (2006).
24. Lilly, M. et al. The effect of increased yeast alcohol acetyltransferase and esterase activity on the flavour profiles of wine and distillates. Yeast 23, 641-659 (2006).
25. Mason, A.B. & Dufour, J.P. Alcohol acetyltransferases and the significance of ester synthesis in yeast. Yeast 16, 1287-1298 (2000).
26. Fujii, T., Yoshimoto, H. & Tamai, Y. Acetate ester production by Saccharomyces cerevisiae lacking the ATF1 gene encoding the alcohol acetyltransferase. J. Ferment. Bioeng. 81, 538-542 (1996).
27. Howard, T.P. et al. Synthesis of customized petroleum-replica fuel molecules by targeted modification of free fatty acid pools in Escherichia coli. Proc. Natl. Acad. Sci. USA 110, 7636-7641 (2013).
28. Lin, F., Das, D., Lin, X.N. & Marsh, E.N. Aldehyde-forming fatty acyl-CoA reductase from cyanobacteria: expression, purification and characterization of the recombinant enzyme. FEBS J. 280, 4773-4781 (2013).
29. Schirmer, A., Rude, M.A., Li, X., Popova, E. & del Cardayre, S.B. Microbial biosynthesis of alkanes. Science 329, 559-562 (2010).
30. Mooney, B.P., Miernyk, J.A. & Randall, D.D. The complex fate of ketoacids. Annu. Rev. Plant Biol. 53, 357-375 (2002).
31. Rodriguez, G.M. & Atsumi, S. Isobutyraldehyde production from Escherichia coli by removing aldehyde reductase activity. Microb. Cell Fact. 11, 90 (2012).
32. de la Plaza, M., Fernandez de Palencia, P., Pelaez, C. & Requena, T. Biochemical and molecular characterization of ketoisovalerate decarboxylase, an enzyme involved in the formation of aldehydes from amino acids by Lactococcus lactis. FEMS Microbiol. Lett. 238, 367-374 (2004).
33. Bastian, S. et al. Engineered ketol-acid reductoisomerase and alcohol dehydrogenase enable anaerobic 2-methylpropan-1-ol production at theoretical yield in Escherichia coli. Metab. Eng. 13, 345-352 (2011).
34. Baez, A., Cho, K.M. & Liao, J.C. High-flux isobutanol production using engineered Escherichia coli: a bioreactor study with in situ product removal. Appl. Microbiol. Biotechnol. 90, 1681-1690 (2011).
35. Atsumi, S. et al. Engineering the isobutanol biosynthetic pathway in Escherichia coli by comparison of three aldehyde reductase/alcohol dehydrogenase genes. Appl. Microbiol. Biotechnol. 85, 651-657 (2010).
36. Connor, M.R., Cann, A.F. & Liao, J.C. 3-Methyl-1-butanol production in Escherichia coli: random mutagenesis and two-phase fermentation. Appl. Microbiol. Biotechnol. 86, 1155-1164 (2010).
37. Belas, R. et al. Bacterial bioluminescence: isolation and expression of the luciferase genes from Vibrio harveyi. Science 218, 791-793 (1982).
38. Meighen, E.A. Bacterial bioluminescence: organization, regulation, and application of the lux genes. FASEB J. 7, 1016-1022 (1993).
39. Ferrández, A., Garcia, J.L. & Diaz, E. Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12. J. Bacteriol. 179, 2573-2581 (1997).
40. Lee, S.J., Ko, J.H., Kang, H.Y. & Lee, Y. Coupled expression of MhpE aldolase and MhpF dehydrogenase in Escherichia coli. Biochem. Biophys. Res. Commun. 346, 1009-1015 (2006).
41. Hester, K., Luo, J., Burns, G., Braswell, E.H. & Sokatch, J.R. Purification of active E1?2?2 of Pseudomonas putida branched-chain-oxoacid dehydrogenase. Eur. J. Biochem. 233, 828-836 (1995).
42. Hester, K.L., Luo, J. & Sokatch, J.R. Purification of Pseudonomas Putida branched-chain keto acid dehydrogenase E1 component. Methods Enzymol. 324, 129-138 (2000).
43. Alonso-Gutierrez, J. et al. Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. Metab. Eng. 19, 33-41 (2013).
44. Park, Y.C., Shaffer, C.E. & Bennett, G.N. Microbial formation of esters. Appl. Microbiol. Biotechnol. 85, 13-25 (2009).
45. van den Berg, C., Heeres, A.S., Van der Wielen, L.A. & Straathof, A.J. Simultaneous Clostridial fermentation, lipase-catalyzed esterification, and ester extraction to enrich diesel with butyl butyrate. Biotechnol. Bioeng. 110, 137-142 (2013).
46. Machado, H.B., Dekishima, Y., Luo, H., Lan, E.I. & Liao, J.C. A selection platform for carbon chain elongation using the CoA-dependent pathway to produce linear higher alcohols. Metab. Eng. 14, 504-511 (2012).