Adding value to plant oils and fatty acids: Biological transformation of fatty acids into ω-hydroxycarboxylic, α,ω-dicarboxylic, and ω-aminocarboxylic acids

Journal of Biotechnology

Volumn 216, Issue , 2015, Pages 158-166

  Seo, Joo Hyun ^a   Lee, Sun Mee ^b   Lee, Jinwon ^c   Park, Jin Byung ^a  

^a Ewha Womans University   (South Korea)

^b Kyungil University   (South Korea)

^c Sogang University   (South Korea)

Author keywords

Biotransformation; Fatty acids; , Dicarboxylic acids; Aminocarboxylic acids; Hydroxycarboxylic acids

Indexed keywords

CARBON; CARBOXYLIC ACIDS; CHAINS; OILS AND FATS;

AMINOCARBOXYLIC ACIDS; BIOLOGICAL PRODUCTION; BIOLOGICAL TRANSFORMATION; BIOTRANSFORMATION; DICARBOXYLIC ACID; INDUSTRIAL REQUIREMENTS; LARGE SCALE PRODUCTIONS; LONG CHAIN CARBOXYLIC ACIDS;

FATTY ACIDS;

ALPHA OMEGA DICARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; FATTY ACID; OMEGA AMINOCARBOXYLIC ACID; OMEGA HYDROXYCARBOXYLIC ACID; UNCLASSIFIED DRUG; VEGETABLE OIL; DICARBOXYLIC ACID;

BIOSYNTHESIS; BIOTRANSFORMATION; COVALENT BOND; FATTY ACID METABOLISM; NONHUMAN; OXYGENATION; PRIORITY JOURNAL; REVIEW; METABOLISM; STEREOISOMERISM;

BIOSYNTHETIC PATHWAYS; BIOTRANSFORMATION; DICARBOXYLIC ACIDS; FATTY ACIDS; PLANT OILS; STEREOISOMERISM;

EID: 84951970723     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2015.10.024     Document Type: Review

References (49)

1. Allmann S. Isomers of Green Leaf Volatiles in Nicotiana Attenuata and their Role in Plant-Insect Interactions 2012, University of Amsterdam.
2. Aresta M., Dibenedetto A., Dumeignil F. Biorefinery: From Biomass to Chemicals and Fuels 2012, De Gruyter, Berlin.
3. Balke K., Kadow M., Mallin H., Sass S., Bornscheuer U.T. Discovery, application and protein engineering of Baeyer-Villiger monooxygenases for organic synthesis. Org. Biomol. Chem. 2012, 10:6249-6265.
4. Bevers L.E., Pinkse M.W., Verhaert P.D., Hagen W.R. Oleate hydratase catalyzes the hydration of a nonactivated carbon-carbon bond. J. Bacteriol. 2009, 191:5010-5012.
5. Biermann U., Bornscheuer U., Meier M.A., Metzger J.O., Schafer H.J. Oils and fats as renewable raw materials in chemistry. Angew. Chem. Int. Ed. Engl. 2011, 50:3854-3871.
6. Broadway N.M., Dickinson F.M., Ratledge C. The enzymology of dicarboxylic acid formation by Corynebacterium sp. strain 7E1C grown on n-alkanes. J. Gen. Microbiol. 1993, 139:1337-1344.
7. Buchhaupt M., Guder J.C., Etschmann M.M., Schrader J. Synthesis of green note aroma compounds by biotransformation of fatty acids using yeast cells coexpressing lipoxygenase and hydroperoxide lyase. Appl. Microbiol. Biotechnol. 2012, 93:159-168.
8. Choi K., Jeon B.S., Kim B.C., Oh M.K., Um Y., Sang B.I. In situ biphasic extractive fermentation for hexanoic acid production from sucrose by Megasphaera elsdenii NCIMB 702410. Appl. Biochem. Biotechnol. 2013, 171:1094-1107.
9. Clomburg J.M., Blankschien M.D., Vick J.E., Chou A., Kim S., Gonzalez R. Integrated engineering of β-oxidation reversal and ω-oxidation pathways for the synthesis of medium chain ω-functionalized carboxylic acids. Metab. Eng. 2015, 28:202-212.
10. Craft D.L., Madduri K.M., Eshoo M., Wilson C.R. Identification and characterization of the CYP52 family of Candida tropicalis ATCC 6, important for the conversion of fatty acids and alkanes to α,ω-dicarboxylic acids. Appl. Environ. Microbiol. 2003, 69:5983-5991.
11. Durairaj P., Malla S., Nadarajan S.P., Lee P.G., Jung E., Park H.H., Kim B.G., Yun H. Fungal cytochrome P450 monooxygenases of Fusarium oxysporum for the synthesis of ω-hydroxy fatty acids in engineered Saccharomyces cerevisiae. Microb. Cell Fact. 2015, 14:45.
12. Eschenfeldt W.H., Zhang Y., Samaha H., Stols L., Eirich L.D., Wilson C.R., Donnelly M.I. Transformation of fatty acids catalyzed by cytochrome P450 monooxygenase enzymes of Candida tropicalis. Appl. Environ. Microbiol. 2003, 69:5992-5999.
13. Feussner I., Wasternack C. The lipoxygenase pathway. Ann. Rev. Plant Biol. 2002, 53:275-297.
14. Gigot C., Ongena M., Fauconnier M.-L., Wathelet J.-P., Du Jardin P., Thonart P. The lipoxygenase metabolic pathway in plants: potential for industrial production of natural green leaf volatiles. Biotechnol. Agron. Soc. Environ. 2010, 14:451-460.
15. Grechkin A. Recent developments in biochemistry of the plant lipoxygenase pathway. Prog. Lipid Res. 1998, 37:317-352.
16. Honda Malca S., Scheps D., Kuhnel L., Venegas-Venegas E., Seifert A., Nestl B.M., Hauer B. Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids. Chem. Commun. (Camb.) 2012, 48:5115-5117.
17. Hou C.T. Handbook of Industrial Biocatalysis 2010, CRC Press, London.
18. Huf S., Krügener S., Hirth T., Rupp S., Zibek S. Biotechnological synthesis of long-chain dicarboxylic acids as building blocks for polymers. Eur. J. Lipid Sci. Technol. 2011, 113:548-561.
19. Jang H.-Y., Jeon E.-Y., Baek A.H., Lee S.-M., Park J.-B. Production of ω-hydroxyundec-9-enoic acid and n-heptanoic acid from ricinoleic acid by recombinant E. coli-based biocatalyst. Process Biochem. 2014, 49:617-622.
20. Jang H.-Y., Singha K., Kim H.-H., Kwon Y.-U., Park J.-B. Chemo-enzymatic synthesis of 11-hydroxyundecanoic acid and 1,11-undecanedioic acid from ricinoleic acid. Green Chem. 2015, 10.1039/C1035GC01017A.
21. Jarboe L.R., Royce L.A., Liu P. Understanding biocatalyst inhibition by carboxylic acids. Front. Microbiol. 2013, 4(272).
22. Johnson W. Final report of the amended safety assessment of glyceryl laurate, glyceryl laurate se, glyceryl laurate/oleate, glyceryl adipate, glyceryl alginate, glyceryl arachidate, glyceryl arachidonate, glyceryl behenate, glyceryl caprate, glyceryl caprylate, glyceryl caprylate/caprate, glyceryl citrate/lactate/linoleate/oleate, glyceryl cocoate, glyceryl collagenate, glyceryl erucate, glyceryl hydrogenated rosinate, glyceryl hydrogenated soyate, glyceryl hydroxystearate, glyceryl isopalmitate, glyceryl isostearate, glyceryl isostearate/myristate, glyceryl isostearates, glyceryl lanolate, glyceryl linoleate, glyceryl linolenate, glyceryl montanate, glyceryl myristate, glyceryl isotridecanoate/stearate/adipate, glyceryl oleate se, glyceryl oleate/elaidate, glyceryl palmitate, glyceryl palmitate/stearate, glyceryl palmitoleate, glyceryl pentadecanoate, glyceryl polyacrylate, glyceryl rosinate, glyceryl sesquioleate, glyceryl/sorbitol oleate/hydroxystearate, glyceryl stearate/acetate, glyceryl stearate/maleate, glyceryl tallowate, glyceryl thiopropionate, and glyceryl undecylenate. Int. J. Toxicol. 2004, 23(Suppl. 2):55-94.
23. Johnston J.B., Ouellet H., Podust L.M., Ortiz de Montellano P.R. Structural control of cytochrome P450-catalyzed ω-hydroxylation. Arch. Biochem. Biophys. 2011, 507:86-94.
24. Joo Y.C., Jeong K.W., Yeom S.J., Kim Y.S., Kim Y., Oh D.K. Biochemical characterization and FAD-binding analysis of oleate hydratase from Macrococcus caseolyticus. Biochimie 2012, 94:907-915.
25. Joo Y.C., Seo E.S., Kim Y.S., Kim K.R., Park J.B., Oh D.K. Production of 10-hydroxystearic acid from oleic acid by whole cells of recombinant E. coli containing oleate hydratase from Stenotrophomonas maltophilia. J. Biotechnol. 2012, 158:17-23.
26. Julsing M.K., Schrewe M., Cornelissen S., Hermann I., Schmid A., Buhler B. Outer membrane protein AlkL boosts biocatalytic oxyfunctionalization of hydrophobic substrates in E. coli. Appl. Environ. Microbiol. 2012, 78:5724-5733.
27. Kim S.U., Kim K.R., Kim J.W., Kim S., Kwon Y.U., Oh D.K., Park J.B. Microbial synthesis of plant oxylipins from γ-linolenic acid through designed biotransformation pathways. J. Agric. Food Chem. 2015, 63:2773-2781.
28. Kim K.R., Oh D.K. Production of hydroxy fatty acids by microbial fatty acid-hydroxylation enzymes. Biotechnol. Adv. 2013, 31:1473-1485.
29. Kirmair L., Skerra A. Biochemical analysis of recombinant AlkJ from Pseudomonas putida reveals a membrane-associated, flavin adenine dinucleotide-dependent dehydrogenase suitable for the biosynthetic production of aliphatic aldehydes. Appl. Environ. Microbiol. 2014, 80:2468-2477.
30. Kishimoto N., Yamamoto I., Toraishi K., Yoshioka S., Saito K., Masuda H., Fujita T. Two distinct pathways for the formation of hydroxy FA from linoleic acid by lactic acid bacteria. Lipids 2003, 38:1269-1274.
31. Koszelewski D., Tauber K., Faber K., Kroutil W. ω-Transaminases for the synthesis of non-racemic α-chiral primary amines. Trends Biotechnol. 2010, 28:324-332.
32. Kroha K. Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids. Inform 2004, 15:568-571.
33. Leisch H., Morley K., Lau P.C. Baeyer-Villiger monooxygenases: more than just green chemistry. Chem. Rev. 2011, 111:4165-4222.
34. Lewis D.F.V. Guide to Cytochromes P450: Structure and Function 2001, CRC Press, London. second edition.
35. Lu W., Ness J.E., Xie W., Zhang X., Minshull J., Gross R.A. Biosynthesis of monomers for plastics from renewable oils. J. Am. Chem. Soc. 2010, 132:15451-15455.
36. Miura Y., Fulco A.J. ω-1, ω-2 and ω-3 hydroxylation of long-chain fatty acids, amides and alcohols by a soluble enzyme system from Bacillus megaterium. Biochim. Biophys. Acta 1975, 388:305-317.
37. Oh H.-J., Kim S.-U., Song J.-W., Lee J.-H., Kang W.-R., Jo Y.-S., Kim K.-R., Bornscheuer U.T., Oh D.-K., Park J.-B. Biotransformation of linoleic acid into hydroxy fatty acids and carboxylic acids using a linoleate double bond hydratase as key enzyme. Adv. Synth. Catal. 2015, 357:408-416.
38. Otte K.B., Kirtz M., Nestl B.M., Hauer B. Synthesis of 9-oxononanoic acid, a precursor for biopolymers. ChemSusChem 2013, 6:2149-2156.
39. Park J.Y., Lee S.H., Kim K.R., Park J.B., Oh D.K. Production of 13S-hydroxy-9(Z)-octadecenoic acid from linoleic acid by whole recombinant cells expressing linoleate 13-hydratase from Lactobacillus acidophilus. J. Biotechnol. 2015, 208:1-10.
40. Schörken U., Kempers P. Lipid biotechnology: industrially relevant production processes. Eur. J. Lipid Sci. Technol. 2009, 111:627-645.
41. Schrewe M., Julsing M.K., Lange K., Czarnotta E., Schmid A., Buhler B. Reaction and catalyst engineering to exploit kinetically controlled whole-cell multistep biocatalysis for terminal FAME oxyfunctionalization. Biotechnol. Bioeng. 2014, 111:1820-1830.
42. Schrewe M., Ladkau N., Bühler B., Schmid A. Direct terminal alkylamino-functionalization via multistep biocatalysis in one recombinant whole-cell catalyst. Adv. Synth. Catal. 2013, 355:1693-1697.
43. Scrimgeour C. Chemistry of fatty acids. Bailey's Industrial Oil and Fat Products 2005, John Wiley & Sons, Inc., Hoboken.
44. Sell C. The Chemistry of Fragrances: From Perfumer to Consumer 2006, Royal Society of Chemistry, London.
45. Song J.-W., Jeon E.-Y., Song D.-H., Jang H.-Y., Bornscheuer U.T., Oh D.-K., Park J.-B. Multistep enzymatic synthesis of long-chain α,ω-dicarboxylic and ω-hydroxycarboxylic acids from renewable fatty acids and plant oils. Angew. Chem. Int. Ed. Engl. 2013, 52:2534-2537.
46. Song J.-W., Lee J.-H., Bornscheuer U.T., Park J.-B. Microbial synthesis of medium-chain α,ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids. Adv. Synth. Catal. 2014, 356:1782-1788.
47. Steffen-Munsberg F., Vickers C., Thontowi A., Schätzle S., Meinhardt T., Svedendahl Humble M., Land H., Berglund P., Bornscheuer U.T., Höhne M. Revealing the structural basis of promiscuous amine transaminase activity. ChemCatChem 2013, 5:154-157.
48. USDA World Agricultural Supply and Demand Estimates 2015, United States Department of Agriculture, Washington DC.
49. Volmer J., Schmid A., Buhler B. Guiding bioprocess design by microbial ecology. Curr. Opin. Microbiol. 2015, 25:25-32.