Preparation of 11-hexyloxy-9-undecenoic acid from crude castor oil hydrolysates by recombinant Escherichia coli expressing alcohol dehydrogenase and Baeyer-Villiger monooxygenase

Process Biochemistry

Volumn 51, Issue 3, 2016, Pages 362-368

  Lee, Jae Hoon ^a   Choi, Sung Hee ^a   Hwang, In Yeub ^a   Park, Jin Byung ^b   Han, Ssangsoo ^c   Lee, Hyunil ^c   Park, Chang Ho ^a   Lee, Eun Yeol ^a  

^a Kyung Hee University   (South Korea)

^b Ewha Womans University   (South Korea)

^c Daelim Chemical Co Ltd   (South Korea)

Author keywords

11 hexyloxy 9 undecenoic acid; 12 oxo 9 octadecenoic acid; Alcohol dehydrogenase; Baeyer Villiger monooxygenase; Ricinoleic acid

Indexed keywords

BACTERIA; ESCHERICHIA COLI;

ALCOHOL DEHYDROGENASE; BAEYER-VILLIGER MONOOXYGENASES; BIOLOGICAL CONVERSION; PLATFORM CHEMICALS; PSEUDOMONAS PUTIDA; RECOMBINANT ESCHERICHIA COLI; RICINOLEIC ACID; VOLUMETRIC PRODUCTIVITY;

VEGETABLE OILS;

EID: 84958184341     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2015.12.012     Document Type: Article

References (40)

1. M. Pavaskar, and A. Kshirsagar Global castor oil and Indian monopoly India: Financ. Technol. 1 2013 15 19
2. R.G. Binder, T.H. Applewhite, G.O. Kohler, and L.A. Goldblatt Chromatographie analysis of seed oils. Fatty acid composition of castor oil J. Am. Oil Chem. Soc. 39 1962 513 517
3. M.N. Belgacem, and A. Gandini Materials from vegetable oils: major sources, properties and applications N.B. Mohamed, G. Alessandro, Monomers, Polymers and Composites from Renewable Resources 2008 Elsevier Oxford 39 66
4. Y. Wache, M. Aguedo, A. Choquet, I.L. Gatfield, J.M. Nicaud, and J.M. Belin Role of beta-oxidation enzymes in gamma-decalactone production by the yeast Yarrowia lipolytica Appl. Environ. Microbiol. 67 2001 5700 5704
5. J.W. Song, E.Y. Jeon, D.H. Song, H.Y. Jang, U.T. Bornscheuer, D.K. Oh, and J.B. Park Multistep enzymatic synthesis of long-chain α, ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils Angew. Chem. Int. Edit. 125 2013 2594 2597
6. H.Y. Jang, K. Singha, H.H. Kim, Y.U. Kwon, and J.B. Park Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1, 11- undecanedioic acid from ricinoleic acid Green Chem. 2016 10.1039/C5GC01017A
7. E.Y. Jeon, A.H. Baek, U.T. Bornscheuer, and J.B. Park Enzyme fusion for whole-cell biotransformation of long-chain sec- alcohols into esters Appl. Microbiol. Biotechnol. 99 2015 6267 6275
8. M.J. Cheesman, M.B. Kneller, E.J. Kelly, S.J. Thompson, C.K. Yeung, D.L. Eaton, and A.E. Rettie Purification and characterization of hexahistidine-tagged cyclohexanone monooxygenase expressed in Saccharomyces cerevisiae and E. coli Protein Expr. Purif. 21 2001 81 86
9. S. Franceschini, H.L. van Beek, A. Pennetta, C. Martinoli, M.W. Fraaije, and A. Mattevi Exploring the structural basis of substrate preferences in Baeyer-Villiger monooxygenases. Insight from steroid monooxygenase J. Biol. Chem. 287 2012 22626 22634
10. H.Y. Jang, E.Y. Jeon, A.H. Baek, S.M. Lee, and J.B. Park Production of γ-hydroxyundec-9-enoic acid and n-heptanoic acid from ricinoleic acid by recombinant E. coli-based biocatalyst Process Biochem. 49 2014 617 622
11. W.H. Lee, J.B. Park, K. Park, M.D. Kim, and J.H. Seo Enhanced production of ε-caprolactone by overexpression of NADPH-regenerating glucose 6-phosphate dehydrogenase in recombinant E. coli harboring cyclohexanone monooxygenase gene Appl. Microbiol. Biotechnol. 76 2007 329 338
12. D. Riesenberg High-cell density cultivation of E. coli Curr. Opin. Biotechnol. 2 1991 380 384
13. U. Horn, W. Strittmatter, A. Krebber, U. Knüpfer, M. Kujau, R. Wenderoth, K. Müller, S. Matzku, A. Plückthun, and D. Riesenberg High volumetric yields of functional dimeric mini-antibodies in Esherichia coli, using an optimized expression vector and high-cell density fermentation under non-limited growth conditions Appl. Microbiol. Biotechnol. 46 1996 524 532
14. V. Menart, S. Jevsevar, M. Vilar, A. Trobis, and A. Pavko Constitutive versus thermoinducible expression of heterologous proteins in E. coli based on strong PR, PL promoters from phage lambda Biotechnol. Bioeng. 83 2003 181 190
15. N.A. Valdez-Cruz, L. Caspeta, N.O. Perez, O.T. Ramirez, and M.A. Trujillo-Roldan Production of recombinant proteins in E. coli by the heat inducible expression system based on the phage lambda pL and/or pR promoters Microb. Cell Fact. 9 2010 18
16. J.A. Vasina, M.S. Peterson, and F. Baneyx Scale-up and optimization of the low-temperature inducible cspA promoter system Biotechnol. Prog. 14 1998 714 721
17. A. Baek, E.Y. Jeon, S.M. Lee, and J.B. Park Expression levels of chaperones influence biotransformation activity of recombinant E. coli expressing Micrococcus luteus alcohol dehydrogenase and Pseudomonas putida Baeyer-Villiger monooxygenase Biotechnol. Bioeng. 112 2015 889 895
18. O. Kolaj, S. Spada, S. Robin, and J. Wall Use of folding modulators to improve heterologous protein production in E. coli Microb. Cell Fact. 8 2009 1 17
19. J. Rehdorf, A. Kirschner, and U.T. Bornscheuer Cloning expression and characterization of a Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440 Biotechnol. Lett. 29 2007 1393 1398
20. S. Nallamsetty, and D.S. Waugh A generic protocol for the expression and purification of recombinant proteins in E. coli using a combinatorial His6-maltose binding protein fusion tag Nat. Protoc. 2 2007 383 391
21. K. Ichihara, and F. Yumeto Preparation of fatty acid methyl esters for gas-liquid chromatography J. Lipid Res. 51 2010 635 640
22. B.D. Hames An introduction to polyacrylamide gel electrophoresis B.D. Hames, D. Rickwood, Gel Electrophoresis of Proteins: A Practical Approach 1986 IRL Press Oxford 1 86
23. H. Kakuda, K. Shiroishi, K. Hosono, and S. Ichihara Construction of Pta-Ack pathway deletion mutants of E. coli and characteristic growth profiles of the mutants in a rich medium Biosci. Biotechnol. Biochem. 58 1994 2232 2235
24. G.W. Luli, and W.R. Strohl Comparison of growth, acetate production, and acetate inhibition of E. coli strains in batch and fed-batch fermentations Appl. Environ. Microbiol. 56 1990 1004 1011
25. W.E. Bentley, N. Mirjalili, D.C. Andersen, R.H. Davis, and D.S. Kompala Plasmid-encoded protein: the principal factor in the metabolic burden associated with recombinant bacteria Biotechnol. Bioeng. 35 1990 668 681
26. Y.F. Ko, W.E. Bentley, and W.A. Weigand The effects of cellular energetics on foreign protein production Appl. Biochem. Biotechnol. 50 1995 145 159
27. J.N. Phue, and J. Shiloach Transcription levels of key metabolic genes are the cause for different glucose utilization pathways in E. coli B (BL21) and E. coli K (JM109) J. Biotechnol. 109 2004 21 30
28. J. Shiloach, and R. Fass Growing E. coli to high cell density-a historical perspective on method development Biotechnol. Adv. 23 2005 345 357
29. M. Jeske, and J. Altenbuchner The E. coli rhamnose promoter rhaP BAD is in Pseudomonas putida KT2440 independent of Crp-cAMP activation Appl. Microbiol. Biotechnol. 85 2010 1923 1933
30. A. Wegerer, T. Sun, and J. Altenbuchner Optimization of an E. coli l-rhamnose-inducible expression vector: test of various genetic module combinations BMC Biotechnol. 8 2008 2
31. H. Motejadded, and J. Altenbuchner Construction of a dual-tag system for gene expression, protein affinity purification and fusion protein processing Biotechnol. Lett. 31 2009 543 549
32. D. Scheps, S. Honda Malca, S.M. Richter, K. Marisch, B.M. Nestl, and B. Hauer Synthesis of ω-hydroxy dodecanoic acid based on an engineered CYP153A fusion construct Microb. Biotechnol. 6 2013 694 707
33. A.P. Desbois, and V.J. Smith Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential Appl. Microbiol. Biotwchnol. 85 2010 1629 1642
34. K. Benkendorff, A.R. Davis, C.N. Rogers, and J.B. Bremner Free fatty acids and sterols in the benthic spawn of aquatic molluscs, and their associated antimicrobial properties J. Exp. Mar. Biol. Ecol. 316 2005 29 44
35. J.W. Song, J.H. Lee, U.T. Bornscheuer, and J.B. Park Microbial synthesis of medium-chain α, ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids Adv. Synth. Catal. 356 2014 1782 1788
36. B.H. Lee, H.S. Kim, J.B. Park, and J.W. Lee Whole cell bioconversion of ricinoleic acid to 12-ketooleic acid by recombinant Corynebacterium glutamicum-based biocatalyst J. Microbiol. Biotechnol. 25 2015 452 458
37. V. Alphand, G. Carrea, R. Wohlgemuth, R. Furstoss, and J.M. Woodley Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases Trends Biotechnol. 21 2003 318 323
38. R.M. Lennen, M.A. Kruziki, K. Kumar, R.A. Zinkel, K.E. Burnum, M.S. Lipton, D.R. HooverS.W. Ranatunga, T.M. Wittkopp, W.D. Marner, and B.F. Pfleger Membrane stresses induced by overproduction of free fatty acids in E. coli Appl. Microbiol. Biotechnol. 77 2011 8114 8128
39. S. Schmidt, C. Scherkus, J. Muschiol, U. Menyes, T. Winkler, W. Hummel, H. Gröger, A. Liese, H.-G. Herz, and U.T. Bornscheuer An enzyme cascade synthesis of ε-caprolactone and its oligomers Angew. Chem. Int. Ed. 54 2015 2784 2787
40. S. Schmidt, M. Genz, K. Balke, and U.T. Bornscheuer The effect of disulfide bond introduction and related Cys/Ser mutations on the stability of a cyclohexanone monooxygenase J. Biotechnol. 214 2015 199 211