Production of 1-dodecanol, 1-tetradecanol, and 1,12-dodecanediol through whole-cell biotransformation in Escherichia coli

Applied and Environmental Microbiology

Volumn 84, Issue 4, 2018, Pages

  Hsieh, Shan Chi ^a   Wang, Jung Hao ^a   Lai, Yu Chen ^a   Su, Ching Yeuh ^a   Lee, Kung Ta ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

1,12 dodecanediol; AlkL; CYP153A operon; Fed batch culture; Recombinant E. coli

Indexed keywords

BACTERIA; BATCH CELL CULTURE; CATALYSTS; CHAINS; ESCHERICHIA COLI; FUNCTIONAL POLYMERS; GENE EXPRESSION; HEAVY METALS; HYDROXYLATION; LUBRICANTS; MEDICAL APPLICATIONS;

1,12-DODECANEDIOL; ALKL; CYP153A OPERON; FED-BATCH CULTURES; RECOMBINANT E. COLI;

PARAFFINS;

ALKANE; BIOTRANSFORMATION; CATALYST; CELL; COLIFORM BACTERIUM; GENE EXPRESSION; HIGH PRESSURE; HIGH TEMPERATURE; INDUSTRIAL PRODUCTION; LUBRICANT; OXIDATION; POLYMER;

ESCHERICHIA COLI; MARINOBACTER HYDROCARBONOCLASTICUS; PSEUDOMONAS PUTIDA;

ALCOHOL DERIVATIVE; ALKANE; BACTERIAL PROTEIN; LAURYL ALCOHOL; MIXED FUNCTION OXIDASE;

BATCH CELL CULTURE; BIOTRANSFORMATION; CATALYSIS; CHEMISTRY; ESCHERICHIA COLI; GENETICS; GROWTH, DEVELOPMENT AND AGING; HYDROXYLATION; METABOLISM; OPERON; PROCEDURES;

ALCOHOLS; ALKANES; BACTERIAL PROTEINS; BATCH CELL CULTURE TECHNIQUES; BIOTRANSFORMATION; CATALYSIS; DODECANOL; ESCHERICHIA COLI; HYDROXYLATION; MIXED FUNCTION OXYGENASES; OPERON;

EID: 85041359131     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.01806-17     Document Type: Article

References (35)

1. Youngquist JT, Schumacher MH, Rose JP, Raines TC, Politz MC, Copeland MF, Pfleger BF. 2013. Production of medium chain length fatty alcohols in Escherichia coli. Metab Eng 20:177-186. https://doi.org/10.1016/j .ymben.2013.10.006
2. Griehl W, Ruestem D. 1970. Nylon-12-preparation, properties, and applications. Ind Eng Chem 62:16-22. https://doi.org/10.1021/ie50723a005
3. Huybrechts DRC, Debruycker L, Jacobs PA. 1990. Oxyfunctionalization of alkanes with hydrogen peroxide on titanium silicalite. Nature 345: 240-242. https://doi.org/10.1038/345240a0
4. Fathepure BZ. 2014. Recent studies in microbial degradation of petroleum hydrocarbons in hypersaline environments. Front Microbiol 5:173. https://doi.org/10.3389/fmicb.2014.00173
5. Eschenfeldt WH, Zhang YY, Samaha H, Stols L, Eirich LD, Wilson CR, Donnelly MI. 2003. Transformation of fatty acids catalyzed by cytochrome P450 monooxygenase enzymes of Candida tropicalis. Appl Environ Microbiol 69:5992-5999. https://doi.org/10.1128/AEM.69.10.5992-5999.2003
6. Lu WH, Ness JE, Xie WC, Zhang XY, Minshull J, Gross RA. 2010. Biosynthesis of monomers for plastics from renewable oils. J Am Chem Soc 132:15451-15455. https://doi.org/10.1021/ja107707v
7. Craft DL, Madduri KM, Eshoo M, Wilson CR. 2003. Identification and characterization of the CYP52 family of Candida tropicalis ATCC 20336, important for the conversion of fatty acids and alkanes to alpha, omegadicarboxylic acids. Appl Environ Microbiol 69:5983-5991. https://doi.org/ 10.1128/AEM.69.10.5983-5991.2003
8. van Beilen JB, Funhoff EG. 2007. Alkane hydroxylases involved in microbial alkane degradation. Appl Microbiol Biotechnol 74:13-21. https://doi .org/10.1007/s00253-006-0748-0
9. Nie Y, Chi CQ, Fang H, Liang JL, Lu SL, Lai GL, Tang YQ, Wu XL. 2014. Diverse alkane hydroxylase genes in microorganisms and environments. Sci Rep 4:4968. https://doi.org/10.1038/srep04968
10. Grant C, Woodley JM, Baganz F. 2011. Whole-cell bio-oxidation of n-dodecane using the alkane hydroxylase system of P. putida GPo1 expressed in E. coli. Enzyme Microb Technol 48:480-486. https://doi.org/ 10.1016/j.enzmictec.2011.01.008
11. Grant C, Deszcz D, Wei YC, Martinez-Torres RJ, Morris P, Folliard T, Sreenivasan R, Ward J, Dalby P, Woodley JM, Baganz F. 2014. Identification and use of an alkane transporter plug-in for applications in biocatalysis and whole-cell biosensing of alkanes. Sci Rep 4:5844. https://doi .org/10.1038/srep05844
12. Ladkau N, Assmann M, Schrewe M, Julsing MK, Schmid A, Buhler B. 2016. Efficient production of the nylon 12 monomer omega-aminododecanoic acid methyl ester from renewable dodecanoic acid methyl ester with engineered Escherichia coli. Metab Eng 36:1-9. https://doi.org/10.1016/ j.ymben.2016.02.011
13. Kadisch M, Julsing MK, Schrewe M, Jehmlich N, Scheer B, von Bergen M, Schmid A, Buhler B. 2017. Maximization of cell viability rather than biocatalyst activity improves whole-cell oxyfunctionalization performance. Biotechnol Bioeng 114:874-884. https://doi.org/10.1002/bit .26213
14. van Beilen JB, Funhoff EG, van Loon A, Just A, Kaysser L, Bouza M, Holtackers R, Rothlisberger M, Li Z, Witholt B. 2006. Cytochrome P450 alkane hydroxylases of the CYP153 family are common in alkanedegrading eubacteria lacking integral membrane alkane hydroxylases. Appl Environ Microbiol 72:59-65. https://doi.org/10.1128/AEM.72.1.59-65.2006
15. Scheps D, Honda Malca S, Richter SM, Marisch K, Nestl BM, Hauer B. 2013. Synthesis of omega-hydroxy dodecanoic acid based on an engineered CYP153A fusion construct. Microb Biotechnol 6:694-707. https://doi .org/10.1111/1751-7915.12073
16. Fujii T, Narikawa T, Sumisa F, Arisawa A, Takeda K, Kato J. 2006. Production of alpha, omega-alkanediols using Escherichia coli expressing a cytochrome p450 from Acinetobacter sp OC4. Biosci Biotechnol Biochem 70:1379-1385. https://doi.org/10.1271/bbb.50656
17. Honda Malca S, Scheps D, Kuhnel L, Venegas-Venegas E, Seifert A, Nestl BM, Hauer B. 2012. Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids. Chem Commun (Camb) 48: 5115-5117. https://doi.org/10.1039/c2cc18103g
18. Schrewe M, Julsing MK, Buhler B, Schmid A. 2013. Whole-cell biocatalysis for selective and productive C-O functional group introduction and modification. Chem Soc Rev 42:6346-6377. https://doi.org/10 .1039/c3cs60011d
19. Leon R, Fernandes P, Pinheiro HM, Cabral JMS. 1998. Whole-cell biocatalysis in organic media. Enzyme Microb Technol 23:483-500. https:// doi.org/10.1016/S0141-0229(98)00078-7
20. Grund A, Shapiro J, Fennewald M, Bacha P, Leahy J, Markbreiter K, Nieder M, Toepfer M. 1975. Regulation of alkane oxidation in Pseudomonas putida. J Bacteriol 123:546-556
21. Ratajczak A, Geissdorfer W, Hillen W. 1998. Expression of alkane hydroxylase from Acinetobacter sp. strain ADP1 is induced by a broad range of n-alkanes and requires the transcriptional activator AlkR. J Bacteriol 180:5822-5827
22. Julsing MK, Schrewe M, Cornelissen S, Hermann I, Schmid A, Buhler B. 2012. Outer membrane protein AlkL boosts biocatalytic oxyfunctionalization of hydrophobic substrates in Escherichia coli. Appl Environ Microbiol 78:5724-5733. https://doi.org/10.1128/AEM.00949-12
23. Liang JL, JiangYang JH, Nie Y, Wu XL. 2015. Regulation of the alkane hydroxylase CYP153 gene in a Gram-positive alkane-degrading bacterium, Dietzia sp. strain DQ12-45-1b. Appl Environ Microbiol 82:608-619. https://doi.org/10.1128/AEM.02811-15
24. Moreno R, Ruiz-Manzano A, Yuste L, Rojo F. 2007. The Pseudomonas putida Crc global regulator is an RNA binding protein that inhibits translation of the AlkS transcriptional regulator. Mol Microbiol 64: 665-675. https://doi.org/10.1111/j.1365-2958.2007.05685.x
25. Zimmermann T, Sorg T, Siehler SY, Gerischer U. 2009. Role of Acinetobacter baylyi Crc in catabolite repression of enzymes for aromatic compound catabolism. J Bacteriol 191:2834-2842. https://doi.org/10.1128/ JB.00817-08
26. Moreno R, Hernandez-Arranz S, La Rosa R, Yuste L, Madhushani A, Shingler V, Rojo F. 2015. The Crc and Hfq proteins of Pseudomonas putida cooperate in catabolite repression and formation of ribonucleic acid complexes with specific target motifs. Environ Microbiol 17: 105-118. https://doi.org/10.1111/1462-2920.12499
27. Rodriguez GM, Atsumi S. 2014. Toward aldehyde and alkane production by removing aldehyde reductase activity in Escherichia coli. Metab Eng 25:227-237. https://doi.org/10.1016/j.ymben.2014.07.012
28. Vaysse PJ, Prat L, Mangenot S, Cruveiller S, Goulas P, Grimaud R. 2009. Proteomic analysis of Marinobacter hydrocarbonoclasticus SP17 biofilm formation at the alkane-water interface reveals novel proteins and cellular processes involved in hexadecane assimilation. Res Microbiol 160: 829-837. https://doi.org/10.1016/j.resmic.2009.09.010
29. Mak PJ, Denisov IG. 2018. Spectroscopic studies of the cytochrome P450 reaction mechanisms. Biochim Biophys Acta 1866:178-204. https://doi .org/10.1016/j.bbapap.2017.06.021
30. Williams KP, Gillespie JJ, Sobral BWS, Nordberg EK, Snyder EE, Shallom JM, Dickerman AW. 2010. Phylogeny of Gammaproteobacteria. J Bacteriol 192:2305-2314. https://doi.org/10.1128/JB.01480-09
31. Picataggio S, Rohrer T, Deanda K, Lanning D, Reynolds R, Mielenz J, Eirich LD. 1992. Metabolic engineering of Candida tropicalis for the production of long-chain dicarboxylic acids. Biotechnology 10:894-898
32. Fujii T, Narikawa T, Takeda K, Kato J. 2004. Biotransformation of various alkanes using the Escherichia coli expressing an alkane hydroxylase system from Gordonia sp TF6. Biosci Biotechnol Biochem 68:2171-2177. https://doi.org/10.1271/bbb.68.2171
33. Wood AJL, Weise NJ, Frampton JD, Dunstan MS, Hollas MA, Derrington SR, Lloyd RC, Quaglia D, Parmeggiani F, Leys D, Turner NJ, Flitsch SL. 11 October 2017. Adenylation activity of carboxylic acid reductases enables the synthesis of amides. Angew Chem Int Ed Engl https://doi.org/10 .1002/anie.201707918
34. Omura T, Sato R. 1964. The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239:2379-2385
35. Omura T, Sato R. 1964. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239: 2370-2378