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Applied Microbiology and Biotechnology

, Volume 103, Issue 4, pp 1545–1555 | Cite as

Biotransformation of dicarboxylic acids from vegetable oil–derived sources: current methods and suggestions for improvement

  • Heeseok Lee
  • Yohanes Eko Chandra Sugiharto
  • Hyeokwon Lee
  • Wooyoung Jeon
  • Jungoh Ahn
  • Hongweon LeeEmail author
Mini-Review
  • 291 Downloads

Abstract

Sustainable manufacture of dicarboxylic acids (DCAs), which are used as raw materials for multiple commercial products, has been an area of considerable research interest in recent years. Traditional chemical-based manufacture of DCAs suffers from limitations such as harsh operational conditions and generation of hazardous by-products. Microbiological methods involving DCA production depend on the capability of alkane-assimilating microorganisms, particularly α, ω-oxidation, to metabolize alkanes. Alkanes are still used as the most common substrates for this method, but the use of renewable resources, such as vegetable oil–derived fatty acid methyl esters (FAMEs), offers multiple advantages for the sustainable production of DCA. However, DCA production using FAME, unlike that using alkanes, still has low productivity and process stability, and we have attempted to identify several limiting factors that weaken the competitiveness. This review discusses the current status and suggests solutions to various obstacles to improve the biotransformation process of FAMEs.

Keywords

Dicarboxylic acids Fatty acid methyl esters Renewable resources Biotransformation ω-Oxidation Fatty acid toxicity 

Notes

Funding

This research was supported by the Research Initiative Program (KGM4231713) of Korea Research Institute of Bioscience and Biotechnology, Industry Core Technology Development Project (N10047873), and Global R&D Project (N000677) of the Ministry of Trade, Industry and Energy of Korea.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Ethical approval

This article does not contain any studies with human or animal participants performed by any of the authors.

References

  1. Abghari A, Chen S (2014) Yarrowia lipolytica as an oleaginous cell factory platform for production of fatty acid-based biofuel and bioproducts. Front Energy Res 2:21Google Scholar
  2. Alexandre H, Mathieu B, Charpentier C (1996) Alteration in membrane fluidity and lipid composition, and modulation of H+-ATPase activity in Saccharomyces cerevisiae caused by decanoic acid. Microbiology 142(3):469–475Google Scholar
  3. Beales N (2004) Adaptation of microorganisms to cold temperatures, weak acid preservatives, low pH, and osmotic stress: a review. Compr Rev Food Sci Food Saf 3(1):1–20Google Scholar
  4. Beardslee T, Picataggio S, Hutagalung A, Fahland T (2014) Biological methods for preparing a fatty dicarboxylic acid. US Patent App. No 14/131,174Google Scholar
  5. Beopoulos A, Chardot T, Nicaud J-M (2009) Yarrowia lipolytica: a model and a tool to understand the mechanisms implicated in lipid accumulation. Biochimie 91(6):692–696Google Scholar
  6. Berchmans HJ, Hirata S (2008) Biodiesel production from crude Jatropha curcas L. seed oil with a high content of free fatty acids. Bioresour Technol 99(6):1716–1721Google Scholar
  7. Besada-Lombana PB, Fernandez-Moya R, Fenster J, Da Silva NA (2017) Engineering Saccharomyces cerevisiae fatty acid composition for increased tolerance to octanoic acid. Biotechnol Bioeng 114(7):1531–1538Google Scholar
  8. Bowen CH, Bonin J, Kogler A, Barba-Ostria C, Zhang F (2015) Engineering Escherichia coli for conversion of glucose to medium-chain ω-hydroxy fatty acids and α, ω-dicarboxylic acids. ACS Synth Biol 5(3):200–206Google Scholar
  9. Broadway NM, Dickinson FM, Ratledge C (1993) The enzymology of dicarboxylic acid formation by Corynebacterium sp. strain 7E1C grown on n-alkanes. Microbiology 139(6):1337–1344Google Scholar
  10. Brul S, Coote P (1999) Preservative agents in foods: mode of action and microbial resistance mechanisms. Int J Food Microbiol 50(1-2):1–17Google Scholar
  11. Cao W, Li H, Luo J, Yin J, Wan Y (2017a) High-level productivity of α, ω-dodecanedioic acid with a newly isolated Candida viswanathii strain. J Ind Microbiol Biotechnol 44(8):1191–1202Google Scholar
  12. Cao W, Liu B, Luo J, Yin J, Wan Y (2017b) α, ω-Dodecanedioic acid production by Candida viswanathii ipe-1 with co-utilization of wheat straw hydrolysates and n-dodecane. Bioresour Technol 243:179–187Google Scholar
  13. Cao W, Wang Y, Luo J, Yin J, Wan Y (2018) Improving α, ω-dodecanedioic acid productivity from n-dodecane and hydrolysate of Candida cells by membrane integrated repeated batch fermentation. Bioresour Technol 260:9–15Google Scholar
  14. Cao Z, Gao H, Liu M, Jiao P (2006) Engineering the acetyl-CoA transportation system of Candida tropicalis enhances the production of dicarboxylic acid. Biotechnol J: Healthcare Nutrition. Technology 1(1):68–74Google Scholar
  15. Chan E-C, Cheng C-S, Hsu Y-H (1997) Continuous production of dicarboxylic acid by immobilized Pseudomonas aeruginosa cells. J Ferment Bioeng 83(2):157–160Google Scholar
  16. Chan E-C, Kuo J (1997) Biotransformation of dicarboxylic acid by immobilized Cryptococcus cells. Enzyme Microb Technol 20(8):585–589Google Scholar
  17. Cheng Q, Sanglard D, Vanhanen S, Liu HT, Bombelli P, Smith A, Slabas AR (2005) Candida yeast long chain fatty alcohol oxidase is a c-type haemoprotein and plays an important role in long chain fatty acid metabolism. Biochim Biophys Acta (BBA)-Molecular and Cell Biology of. Lipids 1735(3):192–203Google Scholar
  18. Chikkali S, Mecking S (2012) Refining of plant oils to chemicals by olefin metathesis. Angew Chem Int Ed 51(24):5802–5808Google Scholar
  19. Chung H, Yang JE, Ha JY, Chae TU, Shin JH, Gustavsson M, Lee SY (2015) Bio-based production of monomers and polymers by metabolically engineered microorganisms. Curr Opin Biotechnol 36:73–84Google Scholar
  20. Cornils B, Lappe P, by Staff U (2014) Dicarboxylic Acids, Aliphatic Ullmann's Encyclopedia of Industrial Chemistry, (Ed).  https://doi.org/10.1002/14356007.a08_523.pub3
  21. 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 α, ω-dicarboxylic acids. Appl Environ Microbiol 69(10):5983–5991Google Scholar
  22. Dasgupta S, Hammond WB, Goddard WA (1996) Crystal structures and properties of nylon polymers from theory. J Am Chem Soc 118(49):12291–12301Google Scholar
  23. Desbois AP, Smith VJ (2010) Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential. Appl Microbiol Biotechnol 85(6):1629–1642Google Scholar
  24. Dickinson FM, Wadforth C (1992) Purification and some properties of alcohol oxidase from alkane-grown Candida tropicalis. Biochem J 282(2):325–331Google Scholar
  25. Eirich LD, Craft DL, Steinberg L, Asif A, Eschenfeldt WH, Stols L, Donnelly MI, Wilson CR (2004) Cloning and characterization of three fatty alcohol oxidase genes from Candida tropicalis strain ATCC 20336. Appl Environ Microbiol 70(8):4872–4879Google Scholar
  26. Endoh-Yamagami S, Hirakawa K, Morioka D, Fukuda R, Ohta A (2007) Basic helix-loop-helix transcription factor heterocomplex of Yas1p and Yas2p regulates cytochrome P450 expression in response to alkanes in the yeast Yarrowia lipolytica. Eukaryot Cell 6(4):734–743Google Scholar
  27. Eschenfeldt WH, Zhang Y, 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(10):5992–5999Google Scholar
  28. Fabritius D, Schäfer H-J, Steinbüchel A (1997) Biotransformation of linoleic acid with the Candida tropicalis M25 mutant. Appl Microbiol Biotechnol 48(1):83–87Google Scholar
  29. Fabritius D, Schäfer H, Steinbüchel A (1996) Identification and production of 3-hydroxy-Δ 9-cis-1, 18-octadecenedioic acid by mutants of Candida tropicalis. Appl Microbiol Biotechnol 45(3):342–348Google Scholar
  30. Fukuda H, Kondo A, Noda H (2001) Biodiesel fuel production by transesterification of oils. J Biosci Bioeng 92(5):405–416Google Scholar
  31. Funk I, Rimmel N, Schorsch C, Sieber V, Schmid J (2017a) Production of dodecanedioic acid via biotransformation of low cost plant-oil derivatives using Candida tropicalis. J Ind Microbiol Biotechnol 44(10):1491–1502Google Scholar
  32. Funk I, Sieber V, Schmid J (2017b) Effects of glucose concentration on 1, 18-cis-octadec-9-enedioic acid biotransformation efficiency and lipid body formation in Candida tropicalis. Sci Rep 7(1):13842Google Scholar
  33. Gajdoš P, Ledesma-Amaro R, Nicaud J-M, Čertík M, Rossignol T (2016) Overexpression of diacylglycerol acyltransferase in Yarrowia lipolytica affects lipid body size, number and distribution. FEMS Yeast Res 16(6):fow062Google Scholar
  34. Gangopadhyay S, Nandi S, Ghosh S (2007) Biooxidation of fatty acid distillates to dibasic acids by a mutant of Candida tropicalis. J Oleo Sci 56(1):13–17Google Scholar
  35. Gatter M, Förster A, Bär K, Winter M, Otto C, Petzsch P, Ježková M, Bahr K, Pfeiffer M, Matthäus F (2014) A newly identified fatty alcohol oxidase gene is mainly responsible for the oxidation of long-chain ω-hydroxy fatty acids in Yarrowia lipolytica. FEMS Yeast Res 14(6):858–872Google Scholar
  36. Global Market Insights (2016) Dodecanedioic Acid (DDDA) Market Size by Application (Resins, Powder Coatings, Adhesives, Lubricants), Industry Analysis Report, Regional Outlook (U.S., Germany, UK, China, India), Growth Potential, Price Trends, Competitive Market Share & Forecast, 2016 – 2023 https://www.gminsightscom/industry-analysis/dodecanedioic-acid-DDDA-market-report. Accessed May 2016
  37. Global Market Insights (2017) Sebacic Acid Market Size By Application (Plastisizers, Lubricants, Solvents, Adhesives, Chemical Intermediates), Industry Analysis Report, Regional Outlook (U.S., Canada, Mexico, Germany, UK, France, Italy, Russia, China, India, Japan, South Korea, Australia, Thailand, Malaysia, Indonesia, Brazil, Saudi Arabia, UAE, South Africa), Application Potential, Price Trends, Competitive Market Share & Forecast, 2017 – 2024 https://www.gminsightscom/industry-analysis/sebacic-acid-market. Accessed September 2017
  38. Goswami P, Chinnadayyala SSR, Chakraborty M, Kumar AK, Kakoti A (2013) An overview on alcohol oxidases and their potential applications. Appl Microbiol Biotechnol 97(10):4259–4275Google Scholar
  39. Green KD, Turner MK, Woodley JM (2000) Candida cloacae oxidation of long-chain fatty acids to dioic acids. Enzyme Microb Technol 27(3-5):205–211Google Scholar
  40. Gustavsson M, Lee SY (2016) Prospects of microbial cell factories developed through systems metabolic engineering. Microb Biotechnol 9(5):610–617Google Scholar
  41. Han L, Peng Y, Zhang Y, Chen W, Lin Y, Wang Q (2017) Designing and creating a synthetic omega oxidation pathway in Saccharomyces cerevisiae enables production of medium-chain α, ω-dicarboxylic acids. Front Microbiol 8:2184Google Scholar
  42. Hirakawa K, Kobayashi S, Inoue T, Endoh-Yamagami S, Fukuda R, Ohta A (2009) Yas3p, an Opi1-family transcription factor regulates cytochrome P450 expression in response to n-alkanes in Yarrowia lipolytica. J Biol Chem 284:7126–7137Google Scholar
  43. Hou J, Lages NF, Oldiges M, Vemuri GN (2009) Metabolic impact of redox cofactor perturbations in Saccharomyces cerevisiae. Metab Eng 11(4-5):253–261Google Scholar
  44. Hsieh S-C, Wang J-H, Lai Y-C, Su C-Y, Lee K-T (2017) Production of 1-dodecanol, 1-tetradecanol, and 1, 12-dodecanediol by whole-cell biotransformation in Escherichia coli. Appl Environ Microbiol:01806–01817Google Scholar
  45. Huang F-C, Peter A, Schwab W (2014) Expression and characterization of CYP52 genes involved in the biosynthesis of sophorolipid and alkane metabolism from Starmerella bombicola. Appl Environ Microbiol 80(2):766–776Google Scholar
  46. Huf S, Krügener S, Hirth T, Rupp S, Zibek S (2011) Biotechnological synthesis of long-chain dicarboxylic acids as building blocks for polymers. Eur J Lipid Sci Technol 113(5):548–561Google Scholar
  47. Iwama R, Kobayashi S, Ishimaru C, Ohta A, Horiuchi H, Fukuda R (2016) Functional roles and substrate specificities of twelve cytochromes P450 belonging to CYP52 family in n-alkane assimilating yeast Yarrowia lipolytica. Fungal Genet Biol 91:43–54Google Scholar
  48. Iwama R, Kobayashi S, Ohta A, Horiuchi H, Fukuda R (2014) Fatty aldehyde dehydrogenase multigene family involved in the assimilation of n-alkanes in Yarrowia lipolytica. J Biol Chem M114:596890Google Scholar
  49. Jackson JB (2012) A review of the binding-change mechanism for proton-translocating transhydrogenase. Biochim Biophys Acta (BBA)-Bioenergetics 1817(10):1839–1846Google Scholar
  50. Jarboe LR, Royce LA, Liu P (2013) Understanding biocatalyst inhibition by carboxylic acids. Front Microbiol 4:272Google Scholar
  51. Jiao P, Huang Y, Li S, Hua Y, Za C (2001) Effects and mechanisms of H2O2 on production of dicarboxylic acid. Biotechnol Bioeng 75(4):456–462Google Scholar
  52. Käppeli O, Müller M, Fiechter A (1978) Chemical and structural alterations at the cell surface of Candida tropicalis, induced by hydrocarbon substrate. J Bacteriol 133(2):952–958Google Scholar
  53. Kemp GD, Dickinson FM, Ratledge C (1988) Inducible long chain alcohol oxidase from alkane-grown Candida tropicalis. Appl Microbiol Biotechnol 29(4):370–374Google Scholar
  54. Knothe G (2008) “Designer” biodiesel: optimizing fatty ester composition to improve fuel properties. Energy Fuels 22(2):1358–1364Google Scholar
  55. Kogure T, Horiuchi H, Matsuda H, Arie M, Takagi M, Ohta A (2007) Enhanced induction of cytochromes P450alk that oxidize methyl-ends of n-alkanes and fatty acids in the long-chain dicarboxylic acid-hyperproducing mutant of Candida maltosa. FEMS Microbiol Lett 271(1):106–111Google Scholar
  56. Kroha K (2004) Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids. Inform 15(9):568–571Google Scholar
  57. Ladkau N, Assmann M, Schrewe M, Julsing MK, Schmid A, Bühler B (2016) Efficient production of the Nylon 12 monomer ω-aminododecanoic acid methyl ester from renewable dodecanoic acid methyl ester with engineered Escherichia coli. Metab Eng 36:1–9Google Scholar
  58. Ledesma-Amaro R, Dulermo R, Niehus X, Nicaud J-M (2016) Combining metabolic engineering and process optimization to improve production and secretion of fatty acids. Metabolic engineering 38:38–46Google Scholar
  59. Ledesma-Amaro R, Nicaud J-M (2016) Yarrowia lipolytica as a biotechnological chassis to produce usual and unusual fatty acids. Prog Lipid Res 61:40–50Google Scholar
  60. Lee H, Han C, Lee H-W, Park G, Jeon W, Ahn J, Lee H (2018) Development of a promising microbial platform for the production of dicarboxylic acids from biorenewable resources. Biotechnol Biofuels 11(1):310Google Scholar
  61. Lee H, Sugiharto YEC, Lee S, Park G, Han C, Jang H, Jeon W, Park H, Ahn J, Kang K (2017) Characterization of the newly isolated ω-oxidizing yeast Candida sorbophila DS02 and its potential applications in long-chain dicarboxylic acid production. Appl Microbiol Biotechnol 101(16):6333–6342Google Scholar
  62. Lee W-H, Kim J-W, Park E-H, Han NS, Kim M-D, Seo J-H (2013a) Effects of NADH kinase on NADPH-dependent biotransformation processes in Escherichia coli. Appl Microbiol Biotechnol 97(4):1561–1569Google Scholar
  63. Lee W-H, Kim M-D, Jin Y-S, Seo J-H (2013b) Engineering of NADPH regenerators in Escherichia coli for enhanced biotransformation. Appl Microbiol Biotechnol 97(7):2761–2772Google Scholar
  64. Lin R, Cao Z, Zhu T, Zhang Z (2000) Secretion in long-chain dicarboxylic acid fermentation. Bioprocess Eng 22(5):391–396Google Scholar
  65. Liu P, Chernyshov A, Najdi T, Fu Y, Dickerson J, Sandmeyer S, Jarboe L (2013) Membrane stress caused by octanoic acid in Saccharomyces cerevisiae. Appl Microbiol Biotechnol 97(7):3239–3251Google Scholar
  66. Liu S, Li C, Fang X, Za C (2004) Optimal pH control strategy for high-level production of long-chain α, ω-dicarboxylic acid by Candida tropicalis. Enzyme Microb Technol 34(1):73–77Google Scholar
  67. Lu W, Ness JE, Xie W, Zhang X, Minshull J, Gross RA (2010) Biosynthesis of monomers for plastics from renewable oils. J Am Chem Soc 132(43):15451–15455Google Scholar
  68. Ma F, Hanna MA (1999) Biodiesel production: a review. Bioresour Technol 70(1):1–15Google Scholar
  69. Marella ER, Holkenbrink C, Siewers V, Borodina I (2018) Engineering microbial fatty acid metabolism for biofuels and biochemicals. Curr Opin Biotechnol 50:39–46Google Scholar
  70. Markham KA, Alper HS (2018) Synthetic biology expands the industrial potential of Yarrowia lipolytica. Trends Biotechnol 36:1085–1095Google Scholar
  71. Mauersberger S, Drechsler H, Oehme G, Müller H-G (1992) Substrate specificity and stereoselectivity of fatty alcohol oxidase from the yeast Candida maltosa. Appl Microbiol Biotechnol 37(1):66–73Google Scholar
  72. Metzger JO (2009) Fats and oils as renewable feedstock for chemistry. Eur J Lipid Sci Technol 111(9):865–876Google Scholar
  73. Mishra P, Park GY, Lakshmanan M, Lee HS, Lee H, Chang MW, Ching CB, Ahn J, Lee DY (2016) Genome-scale metabolic modeling and in silico analysis of lipid accumulating yeast Candida tropicalis for dicarboxylic acid production. Biotechnol Bioeng 113(9):1993–2004Google Scholar
  74. Miyagi H, Kawai S, Murata K (2009) Two sources of mitochondrial NADPH in the yeast Saccharomyces cerevisiae. J Biol Chem 284(12):7553–7560Google Scholar
  75. Ngo HL, Foglia TA (2007) Synthesis of long chain unsaturated-α, ω-dicarboxylic acids from renewable materials via olefin metathesis. J Am Oil Chem Soc 84(8):777–784Google Scholar
  76. Nicaud JM (2012) Yarrowia lipolytica. Yeast 29(10):409–418Google Scholar
  77. Nissen TL, Anderlund M, Nielsen J, Villadsen J, Kielland-Brandt MC (2001) Expression of a cytoplasmic transhydrogenase in Saccharomyces cerevisiae results in formation of 2-oxoglutarate due to depletion of the NADPH pool. Yeast 18(1):19–32Google Scholar
  78. Pötter M, Hennemann H-G, Schaffer S, Haas T (2011) Candida tropicalis cells and use thereof. U.S. Patent App. No 12(/943):145Google Scholar
  79. Picataggio S, Beardslee T (2012) Biological methods for preparing adipic acid. US Patent No 8,241,879Google Scholar
  80. 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. Nat Biotechnol 10(8):894–898Google Scholar
  81. Rajendran G, Zhang C, Gaffney A (2015) NYLON POLYMER AND PROCESS. US Patent App. 14(/375):036Google Scholar
  82. Royce LA, Liu P, Stebbins MJ, Hanson BC, Jarboe LR (2013) The damaging effects of short chain fatty acids on Escherichia coli membranes. Appl Microbiol Biotechnol 97(18):8317–8327Google Scholar
  83. Royce LA, Yoon JM, Chen Y, Rickenbach E, Shanks JV, Jarboe LR (2015) Evolution for exogenous octanoic acid tolerance improves carboxylic acid production and membrane integrity. Metab Eng 29:180–188Google Scholar
  84. Sathesh-Prabu C, Lee SK (2015) Production of long-chain α, ω-dicarboxylic acids by engineered Escherichia coli from renewable fatty acids and plant oils. J Agric Food Chem 63(37):8199–8208Google Scholar
  85. Schörken U, Kempers P (2009) Lipid biotechnology: industrially relevant production processes. Eur J Lipid Sci Technol 111(7):627–645Google Scholar
  86. Scheller U, Zimmer T, Becher D, Schauer F, Schunck W-H (1998) Oxygenation cascade in conversion of n-alkanes to α, ω-dioic acids catalyzed by cytochrome P450 52A3. J Biol Chem 273(49):32528–32534Google Scholar
  87. Smit MS, Mokgoro MM, Setati E, Nicaud J-M (2005) α, ω-Dicarboxylic acid accumulation by acyl-CoA oxidase deficient mutants of Yarrowia lipolytica. Biotechnol Lett 27(12):859–864Google Scholar
  88. Song JW, Jeon EY, Song DH, Jang HY, Bornscheuer UT, Oh DK, Park JB (2013) Multistep enzymatic synthesis of long-chain α, ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils. Angew Chem Int Ed 52(9):2534–2537Google Scholar
  89. Spaans SK, Weusthuis RA, Van Der Oost J, Kengen SW (2015) NADPH-generating systems in bacteria and archaea. Front Microbiol 6:742Google Scholar
  90. Stratford M, Anslow P (1996) Comparison of the inhibitory action on Saccharomyces cerevisiae of weak-acid preservatives, uncouplers, and medium-chain fatty acids. FEMS Microbiol Lett 142(1):53–58Google Scholar
  91. Sugiharto YEC, Lee H, Fitriana AD, Lee H, Jeon W, Park K, Ahn J, Lee H (2018) Effect of decanoic acid and 10-hydroxydecanoic acid on the biotransformation of methyl decanoate to sebacic acid. AMB Express 8(1):75Google Scholar
  92. Takahashi F, Igarashi K, Hagihara H (2016) Identification of the fatty alcohol oxidase FAO1 from Starmerella bombicola and improved novel glycolipids production in an FAO1 knockout mutant. Appl Microbiol Biotechnol 100(22):9519–9528Google Scholar
  93. Tetzlaf D (2017) Verdezyne Ground breaking Ceremony in Malaysia Commemorates Initiation Of The World's First Biobased DDDA Plant. https://verdezyne.com/uncategorized/verdezyne-groundbreaking-ceremony-in-malaysia-commemorates-initiation-of-the-worlds-first-biobased-ddda-plant/. Accessed 31 July 2017
  94. Uchio R, Shiio I (1972a) Microbial Production of Long-chain Dicarboxylic Acids from n-Alkanes: Part II. Production by Candida cloacae Mutant Unable to Assimilate Dicarboxylic Acid. Agric Biol Chem 36(3):426–433Google Scholar
  95. Uchio R, Shiio I (1972b) Production of dicarboxylic acids by Candida cloacae mutant unable to assimilate n-alkane. Agric Biol Chem 36(7):1169–1175Google Scholar
  96. Van Bogaert IN, Demey M, Develter D, Soetaert W, Vandamme EJ (2009a) Importance of the cytochrome P450 monooxygenase CYP52 family for the sophorolipid-producing yeast Candida bombicola. FEMS Yeast Res 9(1):87–94Google Scholar
  97. Van Bogaert IN, Sabirova J, Develter D, Soetaert W, Vandamme EJ (2009b) Knocking out the MFE-2 gene of Candida bombicola leads to improved medium-chain sophorolipid production. FEMS Yeast Res 9(4):610–617Google Scholar
  98. Van Bogaert IN, Saerens K, De Muynck C, Develter D, Soetaert W, Vandamme EJ (2007) Microbial production and application of sophorolipids. Appl Microbiol Biotechnol 76(1):23–34Google Scholar
  99. Van Gerpen J (2005) Biodiesel processing and production. Fuel Process Technol 86(10):1097–1107Google Scholar
  100. Wang J, Ding H, He L, SUN Y, ZHANG J (2011) Influence of growth factor and emulsifier on dodecanedioic acid fermentation by Candida tropicalis. China Brew 5:87–89Google Scholar
  101. Werner N, Dreyer M, Wagner W, Papon N, Rupp S, Zibek S (2017) Candida guilliermondii as a potential biocatalyst for the production of long-chain α, ω-dicarboxylic acids. Biotechnol Lett 39(3):429–438Google Scholar
  102. Werner N, Zibek S (2017) Biotechnological production of bio-based long-chain dicarboxylic acids with oleogenious yeasts. World J Microbiol Biotechnol 33(11):194Google Scholar
  103. Yamada T, Nawa H, Kawamoto S, Tanaka A, Fukui S (1980) Subcellular localization of long-chain alcohol dehydrogenase and aldehyde dehydrogenase in n-alkane-grown Candida tropicalis. Arch Microbiol 128(2):145–151Google Scholar
  104. Yu J-L, Xia X-X, Zhong J-J, Qian Z-G (2017) Enhanced production of C5 dicarboxylic acids by aerobic-anaerobic shift in fermentation of engineered Escherichia coli. Process Biochem 62:53–58Google Scholar

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© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Biotechnology Process Engineering CenterKorean Research Institute of Bioscience and Biotechnology (KRIBB)Cheongju-siRepublic of Korea
  2. 2.Department of Bioprocess Engineering, KRIBB School of BiotechnologyKorea University of Science and Technology (UST)DaejeonRepublic of Korea
  3. 3.Process Engineering DivisionPT Rekayasa IndustriJakartaIndonesia

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