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

[1]  H. Lee,et al.  Development of a promising microbial platform for the production of dicarboxylic acids from biorenewable resources , 2018, Biotechnology for Biofuels.

[2]  Hal S Alper,et al.  Synthetic Biology Expands the Industrial Potential of Yarrowia lipolytica. , 2018, Trends in biotechnology.

[3]  Jianquan Luo,et al.  Improving α, ω-dodecanedioic acid productivity from n-dodecane and hydrolysate of Candida cells by membrane integrated repeated batch fermentation. , 2018, Bioresource technology.

[4]  Jungoh Ahn,et al.  Effect of decanoic acid and 10-hydroxydecanoic acid on the biotransformation of methyl decanoate to sebacic acid , 2018, AMB Express.

[5]  V. Siewers,et al.  Engineering microbial fatty acid metabolism for biofuels and biochemicals. , 2018, Current opinion in biotechnology.

[6]  Shan-Chi Hsieh,et al.  Production of 1-Dodecanol, 1-Tetradecanol, and 1,12-Dodecanediol through Whole-Cell Biotransformation in Escherichia coli , 2017, Applied and Environmental Microbiology.

[7]  Qinhong Wang,et al.  Designing and Creating a Synthetic Omega Oxidation Pathway in Saccharomyces cerevisiae Enables Production of Medium-Chain α, ω-Dicarboxylic Acids , 2017, Front. Microbiol..

[8]  Bin Liu,et al.  α, ω-Dodecanedioic acid production by Candida viswanathii ipe-1 with co-utilization of wheat straw hydrolysates and n-dodecane. , 2017, Bioresource technology.

[9]  Xiao-Xia Xia,et al.  Enhanced production of C5 dicarboxylic acids by aerobic-anaerobic shift in fermentation of engineered Escherichia coli , 2017 .

[10]  J. Schmid,et al.  Effects of glucose concentration on 1,18-cis-octadec-9-enedioic acid biotransformation efficiency and lipid body formation in Candida tropicalis , 2017, Scientific Reports.

[11]  S. Zibek,et al.  Biotechnological production of bio-based long-chain dicarboxylic acids with oleogenious yeasts , 2017, World journal of microbiology & biotechnology.

[12]  J. Schmid,et al.  Production of dodecanedioic acid via biotransformation of low cost plant-oil derivatives using Candida tropicalis , 2017, Journal of Industrial Microbiology & Biotechnology.

[13]  N. D. Da Silva,et al.  Engineering Saccharomyces cerevisiae fatty acid composition for increased tolerance to octanoic acid , 2017, Biotechnology and bioengineering.

[14]  Jungoh Ahn,et al.  Characterization of the newly isolated ω-oxidizing yeast Candida sorbophila DS02 and its potential applications in long-chain dicarboxylic acid production , 2017, Applied Microbiology and Biotechnology.

[15]  Jianquan Luo,et al.  High-level productivity of α,ω-dodecanedioic acid with a newly isolated Candida viswanathii strain , 2017, Journal of Industrial Microbiology & Biotechnology.

[16]  M. Dreyer,et al.  Candida guilliermondii as a potential biocatalyst for the production of long-chain α,ω-dicarboxylic acids , 2017, Biotechnology Letters.

[17]  J. Nicaud,et al.  Combining metabolic engineering and process optimization to improve production and secretion of fatty acids. , 2016, Metabolic engineering.

[18]  M. Čertík,et al.  Overexpression of diacylglycerol acyltransferase in Yarrowia lipolytica affects lipid body size, number and distribution. , 2016, FEMS yeast research.

[19]  C. Ching,et al.  Genome‐scale metabolic modeling and in silico analysis of lipid accumulating yeast Candida tropicalis for dicarboxylic acid production , 2016, Biotechnology and bioengineering.

[20]  Sang Yup Lee,et al.  Prospects of microbial cell factories developed through systems metabolic engineering , 2016, Microbial biotechnology.

[21]  H. Hagihara,et al.  Identification of the fatty alcohol oxidase FAO1 from Starmerella bombicola and improved novel glycolipids production in an FAO1 knockout mutant , 2016, Applied Microbiology and Biotechnology.

[22]  A. Schmid,et al.  Efficient production of the Nylon 12 monomer ω-aminododecanoic acid methyl ester from renewable dodecanoic acid methyl ester with engineered Escherichia coli. , 2016, Metabolic engineering.

[23]  R. Fukuda,et al.  Functional roles and substrate specificities of twelve cytochromes P450 belonging to CYP52 family in n-alkane assimilating yeast Yarrowia lipolytica. , 2016, Fungal genetics and biology : FG & B.

[24]  Fuzhong Zhang,et al.  Engineering Escherichia coli for Conversion of Glucose to Medium-Chain ω-Hydroxy Fatty Acids and α,ω-Dicarboxylic Acids. , 2016, ACS synthetic biology.

[25]  Tong Un Chae,et al.  Bio-based production of monomers and polymers by metabolically engineered microorganisms. , 2015, Current opinion in biotechnology.

[26]  Sung Kuk Lee,et al.  Production of Long-Chain α,ω-Dicarboxylic Acids by Engineered Escherichia coli from Renewable Fatty Acids and Plant Oils. , 2015, Journal of agricultural and food chemistry.

[27]  J. van der Oost,et al.  NADPH-generating systems in bacteria and archaea , 2015, Front. Microbiol..

[28]  L. Jarboe,et al.  Evolution for exogenous octanoic acid tolerance improves carboxylic acid production and membrane integrity. , 2015, Metabolic engineering.

[29]  Boy Cornils,et al.  Dicarboxylic Acids, Aliphatic , 2014 .

[30]  R. Fukuda,et al.  Fatty Aldehyde Dehydrogenase Multigene Family Involved in the Assimilation of n-Alkanes in Yarrowia lipolytica* , 2014, The Journal of Biological Chemistry.

[31]  G. Barth,et al.  A newly identified fatty alcohol oxidase gene is mainly responsible for the oxidation of long-chain ω-hydroxy fatty acids in Yarrowia lipolytica. , 2014, FEMS yeast research.

[32]  Shu-lin Chen,et al.  Yarrowia lipolytica as an Oleaginous Cell Factory Platform for Production of Fatty Acid-Based Biofuel and Bioproducts , 2014, Front. Energy Res..

[33]  W. Schwab,et al.  Expression and Characterization of CYP52 Genes Involved in the Biosynthesis of Sophorolipid and Alkane Metabolism from Starmerella bombicola , 2013, Applied and Environmental Microbiology.

[34]  L. Jarboe,et al.  Understanding biocatalyst inhibition by carboxylic acids , 2013, Front. Microbiol..

[35]  L. Jarboe,et al.  The damaging effects of short chain fatty acids on Escherichia coli membranes , 2013, Applied Microbiology and Biotechnology.

[36]  Somasekhar R. Chinnadayyala,et al.  An overview on alcohol oxidases and their potential applications , 2013, Applied Microbiology and Biotechnology.

[37]  L. Jarboe,et al.  Membrane stress caused by octanoic acid in Saccharomyces cerevisiae , 2013, Applied Microbiology and Biotechnology.

[38]  U. Bornscheuer,et al.  Multistep enzymatic synthesis of long-chain α,ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils. , 2013, Angewandte Chemie.

[39]  Yong‐Su Jin,et al.  Engineering of NADPH regenerators in Escherichia coli for enhanced biotransformation , 2013, Applied Microbiology and Biotechnology.

[40]  Myoung-Dong Kim,et al.  Effects of NADH kinase on NADPH-dependent biotransformation processes in Escherichia coli , 2013, Applied Microbiology and Biotechnology.

[41]  J. Nicaud.  Yarrowia lipolytica , 2012, Yeast.

[42]  J. Jackson.  A review of the binding-change mechanism for proton-translocating transhydrogenase. , 2012, Biochimica et biophysica acta.

[43]  Samir H. Chikkali,et al.  Refining of plant oils to chemicals by olefin metathesis. , 2012, Angewandte Chemie.

[44]  S. Zibek,et al.  Biotechnological synthesis of long-chain dicarboxylic acids as building blocks for polymers , 2011 .

[45]  J. Ness,et al.  Biosynthesis of monomers for plastics from renewable oils. , 2010, Journal of the American Chemical Society.

[46]  A. Desbois,et al.  Antibacterial free fatty acids: activities, mechanisms of action and biotechnological potential , 2010, Applied Microbiology and Biotechnology.

[47]  Jürgen O. Metzger,et al.  FATS AND OILS AS RENEWABLE FEEDSTOCK FOR CHEMISTRY , 2009 .

[48]  M. Oldiges,et al.  Metabolic impact of redox cofactor perturbations in Saccharomyces cerevisiae. , 2009, Metabolic engineering.

[49]  Ulrich Schörken,et al.  Lipid biotechnology: Industrially relevant production processes , 2009 .

[50]  J. Nicaud,et al.  Yarrowia lipolytica: A model and a tool to understand the mechanisms implicated in lipid accumulation. , 2009, Biochimie.

[51]  W. Soetaert,et al.  Knocking out the MFE-2 gene of Candida bombicola leads to improved medium-chain sophorolipid production. , 2009, FEMS yeast research.

[52]  S. Kawai,et al.  Two Sources of Mitochondrial NADPH in the Yeast Saccharomyces cerevisiae* , 2009, Journal of Biological Chemistry.

[53]  R. Fukuda,et al.  Yas3p, an Opi1 Family Transcription Factor, Regulates Cytochrome P450 Expression in Response to n-Alkanes in Yarrowia lipolytica* , 2009, Journal of Biological Chemistry.

[54]  M. De Mey,et al.  Importance of the cytochrome P450 monooxygenase CYP52 family for the sophorolipid-producing yeast Candida bombicola. , 2009, FEMS yeast research.

[55]  H. J. Berchmans,et al.  Biodiesel production from crude Jatropha curcas L. seed oil with a high content of free fatty acids. , 2008, Bioresource technology.

[56]  Gerhard Knothe,et al.  “Designer” Biodiesel: Optimizing Fatty Ester Composition to Improve Fuel Properties† , 2008 .

[57]  T. Foglia,et al.  Synthesis of Long Chain Unsaturated-α,ω-Dicarboxylic Acids from Renewable Materials via Olefin Metathesis , 2007 .

[58]  A. Ohta,et al.  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. , 2007, FEMS microbiology letters.

[59]  Wim Soetaert,et al.  Microbial production and application of sophorolipids , 2007, Applied Microbiology and Biotechnology.

[60]  R. Fukuda,et al.  Basic Helix-Loop-Helix Transcription Factor Heterocomplex of Yas1p and Yas2p Regulates Cytochrome P450 Expression in Response to Alkanes in the Yeast Yarrowia lipolytica , 2007, Eukaryotic Cell.

[61]  Ming Liu,et al.  Engineering the acetyl‐CoA transportation system of candida tropicalis enhances the production of dicarboxylic acid , 2006, Biotechnology journal.

[62]  Alison G. Smith,et al.  Candida yeast long chain fatty alcohol oxidase is a c-type haemoprotein and plays an important role in long chain fatty acid metabolism. , 2005, Biochimica et biophysica acta.

[63]  J. V. Gerpen,et al.  Biodiesel processing and production , 2005 .

[64]  J. Nicaud,et al.  α,ω-Dicarboxylic acid accumulation by acyl-CoA oxidase deficient mutants of Yarrowia lipolytica , 2005, Biotechnology Letters.

[65]  L. Stols,et al.  Cloning and Characterization of Three Fatty Alcohol Oxidase Genes from Candida tropicalis Strain ATCC 20336 , 2004, Applied and Environmental Microbiology.

[66]  C. Li,et al.  Optimal pH control strategy for high-level production of long-chain α, ω-dicarboxylic acid by Candida tropicalis , 2004 .

[67]  N Beales,et al.  Adaptation of Microorganisms to Cold Temperatures, Weak Acid Preservatives, Low pH, and Osmotic Stress: A Review. , 2004, Comprehensive reviews in food science and food safety.

[68]  C. R. Wilson,et al.  Transformation of Fatty Acids Catalyzed by Cytochrome P450 Monooxygenase Enzymes of Candida tropicalis , 2003, Applied and Environmental Microbiology.

[69]  D. Craft,et al.  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 , 2003, Applied and Environmental Microbiology.

[70]  Z. Cao,et al.  Effects and mechanisms of H(2)O(2) on production of dicarboxylic acid. , 2001, Biotechnology and bioengineering.

[71]  J. Nielsen,et al.  Expression of a cytoplasmic transhydrogenase in Saccharomyces cerevisiae results in formation of 2‐oxoglutarate due to depletion of the NADPH pool , 2001, Yeast.

[72]  Green,et al.  Candida cloacae oxidation of long-chain fatty acids to dioic acids. , 2000, Enzyme and microbial technology.

[73]  Z. Cao,et al.  Secretion in long-chain dicarboxylic acid fermentation , 2000 .

[74]  M. Hanna,et al.  Role of miR-10b in breast cancer metastasis , 2010, Breast Cancer Research.

[75]  S. Brul,et al.  Preservative agents in foods. Mode of action and microbial resistance mechanisms. , 1999, International journal of food microbiology.

[76]  D. Becher,et al.  Oxygenation Cascade in Conversion of n-Alkanes to α,ω-Dioic Acids Catalyzed by Cytochrome P450 52A3* , 1998, The Journal of Biological Chemistry.

[77]  A. Steinbüchel,et al.  Biotransformation of linoleic acid with the Candida tropicalis M25 mutant , 1997, Applied Microbiology and Biotechnology.

[78]  Jimmy Kuo,et al.  Biotransformation of dicarboxylic acid by immobilized Cryptococcus cells , 1997 .

[79]  W. Goddard,et al.  Crystal Structures and Properties of Nylon Polymers from Theory , 1996 .

[80]  M. Stratford,et al.  Comparison of the inhibitory action on Saccharomyces cerevisiae of weak-acid preservatives, uncouplers, and medium-chain fatty acids. , 1996, FEMS microbiology letters.

[81]  A. Steinbüchel,et al.  Identification and production of 3-hydroxy-Δ9-cis-1,18-octadecenedioic acid by mutants of Candida tropicalis , 1996, Applied Microbiology and Biotechnology.

[82]  H. Alexandre,et al.  Alteration in membrane fluidity and lipid composition, and modulation of H(+)-ATPase activity in Saccharomyces cerevisiae caused by decanoic acid. , 1996, Microbiology.

[83]  Colin Ratledge,et al.  The enzymology of dicarboxylic acid formation by Corynebacterium sp. strain 7E1C grown on n-alkanes , 1993 .

[84]  J. Mielenz,et al.  Metabolic Engineering of Candida Tropicalis for the Production of Long–Chain Dicarboxylic Acids , 1992, Bio/Technology.

[85]  H. Müller,et al.  Substrate specificity and stereoselectivity of fatty alcohol oxidase from the yeast Candida maltosa , 1992, Applied Microbiology and Biotechnology.

[86]  F. Dickinson,et al.  Purification and some properties of alcohol oxidase from alkane-grown Candida tropicalis. , 1992, The Biochemical journal.

[87]  Glenwyn D. Kemp,et al.  Inducible long chain alcohol oxidase from alkane-grown Candida tropicalis , 1988, Applied Microbiology and Biotechnology.

[88]  H. Nawa,et al.  Subcellular localization of long-chain alcohol dehydrogenase and aldehyde dehydrogenase in n-alkane-grown Candida tropicalis , 1980, Archives of Microbiology.

[89]  O. Käppeli,et al.  Chemical and structural alterations at the cell surface of Candida tropicalis, induced by hydrocarbon substrate , 1978, Journal of bacteriology.

[90]  I. Shiio,et al.  Production of Dicarboxylic Acids byCandida cloacaeMutant Unable to Assimilaten-Alkane , 1972 .

[91]  I. Shiio,et al.  Microbial Production of Long-chain Dicarboxylic Acids from n -Alkanes Part II:Production by Candida cloacae Mutant Unable to Assimilate Dicarboxylic Acid , 1972 .

[92]  Rodrigo Ledesma-Amaro,et al.  Yarrowia lipolytica as a biotechnological chassis to produce usual and unusual fatty acids. , 2016, Progress in lipid research.

[93]  A. Steinbüchel,et al.  Yarrowia lipolytica , 2013, Microbiology Monographs.

[94]  Zhang Jubin.  Influence of growth factor and emulsifier on dodecanedioic acid fermentation by Candida tropicalis , 2011 .

[95]  S. Nandi,et al.  Biooxidation of fatty acid distillates to dibasic acids by a mutant of Candida tropicalis. , 2006, Journal of oleo science.

[96]  A. Kondo,et al.  Biodiesel fuel production by transesterification of oils. , 2001, Journal of bioscience and bioengineering.

[97]  Err-Cheng Chan,et al.  Continuous production of dicarboxylic acid by immobilized Pseudomonas aeruginosa cells , 1997 .

[98]  I. Shiio,et al.  Production of Dicarboxylic Acids by Candida cloacae Mutant Unable to Assimilate n-Alkane , 1972 .