Microbial synthesis of plant oxylipins from γ-linolenic acid through designed biotransformation pathways

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 10, 2015, Pages 2773-2781

  Kim, Sae Um ^a   Kim, Kyoung Rok ^b   Kim, Ji Won ^a   Kim, Soomin ^a   Kwon, Yong Uk ^a   Oh, Deok Kun ^b   Park, Jin Byung ^a  

^a Ewha Womans University   (South Korea)

^b Konkuk University   (South Korea)

Author keywords

biotransformation; Escherichia coli; plant oxylipins; whole cell biocatalysis; linolenic acid

Indexed keywords

BIOCATALYSTS; BIOCHEMISTRY; BIOCONVERSION; BIOSYNTHESIS; CARBOXYLIC ACIDS; CATALYSIS; CELLS; CYTOLOGY; ENZYMES; ESCHERICHIA COLI; METABOLITES; UNSATURATED FATTY ACIDS;

BAEYER-VILLIGER MONOOXYGENASES; BIOTRANSFORMATION; BIOTRANSFORMATION PATHWAYS; LINOLENIC ACIDS; PLANT OXYLIPINS; RECOMBINANT ESCHERICHIA COLI; UNSATURATED CARBOXYLIC ACIDS; WHOLE-CELL BIOCATALYSIS;

FATTY ACIDS;

ESCHERICHIA COLI;

GAMMA LINOLENIC ACID; OXYLIPIN;

BIOSYNTHESIS; BIOTRANSFORMATION; ESCHERICHIA COLI; GENETICS; METABOLIC ENGINEERING; METABOLISM;

BIOSYNTHETIC PATHWAYS; BIOTRANSFORMATION; ESCHERICHIA COLI; GAMMA-LINOLENIC ACID; METABOLIC ENGINEERING; OXYLIPINS;

EID: 84924940097     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5058843     Document Type: Article

References (40)

1. Rodriguez, G. M.; Tashiro, Y.; Atsumi, S. Expanding ester biosynthesis in Escherichia coli Nat. Chem. Biol. 2014, 10, 259-265
2. Bornscheuer, U. T.; Huisman, G. W.; Kazlauskas, R. J.; Lutz, S.; Moore, J. C.; Robins, K. Engineering the third wave of biocatalysis Nature 2012, 485, 185-194
3. Lee, J. W.; Na, D.; Park, J. M.; Lee, J.; Choi, S.; Lee, S. Y. Systems metabolic engineering of microorganisms for natural and non-natural chemicals Nat. Chem. Biol. 2012, 8, 536-546
4. Bornscheuer, U. T. Enzymes in lipid modification: past achievements and current trends Eur. J. Lipid Sci. Technol. 2014, 116, 1322-1331
5. Lin, Y.; Jain, R.; Yan, Y. Microbial production of antioxidant food ingredients via metabolic engineering Curr. Opin. Biotechnol. 2014, 26, 71-78
6. Zhao, S.; Kumar, R.; Sakai, A.; Vetting, M. W.; Wood, B. M.; Brown, S.; Bonanno, J. B.; Hillerich, B. S.; Seidel, R. D.; Babbitt, P. C.; Almo, S. C.; Sweedler, J. V.; Gerlt, J. A.; Cronan, J. E.; Jacobson, M. P. Discovery of new enzymes and metabolic pathways by using structure and genome context Nature 2013, 502, 698-702
7. Zhou, J.; Du, G.; Chen, J. Novel fermentation processes for manufacturing plant natural products Curr. Opin. Biotechnol. 2014, 25, 17-23
8. Paddon, C. J.; Westfall, P. J.; Pitera, D. J.; Benjamin, K.; Fisher, K.; McPhee, D.; Leavell, M. D.; Tai, A.; Main, A.; Eng, D.; Polichuk, D. R.; Teoh, K. H.; Reed, D. W.; Treynor, T.; Lenihan, J.; Fleck, M.; Bajad, S.; Dang, G.; Dengrove, D.; Diola, D.; Dorin, G.; Ellens, K. W.; Fickes, S.; Galazzo, J.; Gaucher, S. P.; Geistlinger, T.; Henry, R.; Hepp, M.; Horning, T.; Iqbal, T.; Jiang, H.; Kizer, L.; Lieu, B.; Melis, D.; Moss, N.; Regentin, R.; Secrest, S.; Tsuruta, H.; Vazquez, R.; Westblade, L. F.; Xu, L.; Yu, M.; Zhang, Y.; Zhao, L.; Lievense, J.; Covello, P. S.; Keasling, J. D.; Reiling, K. K.; Renninger, N. S.; Newman, J. D. High-level semi-synthetic production of the potent antimalarial artemisinin Nature 2013, 496, 528-532
9. Jetter, R.; Kunst, L. Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels Plant J. 2008, 54, 670-683
10. Kishimoto, Y.; Radin, N. Occurrence of 2-hydroxy fatty acids in animal tissues J. Lipid Res. 1963, 4, 139-143
11. Kock, J. L. F.; Strauss, C. J.; Pohl, C. H.; Nigam, S. The distribution of 3-hydroxy oxylipins in fungi Prostaglandins Other Lipid Mediat. 2003, 71, 85-96
12. Joo, Y. C.; Oh, D. K. Lipoxygenases: potential starting biocatalysts for the synthesis of signaling compounds Biotechnol. Adv. 2012, 30, 1524-1532
13. Kim, K. R.; Oh, D. K. Production of hydroxy fatty acids by microbial fatty acid-hydroxylation enzymes Biotechnol. Adv. 2013, 31, 1473-1485
14. Suzuki, Y.; Kurita, O.; Kono, Y.; Hyakutake, H.; Sakurai, A. Strcture of a new antifungal C11-hydroxyfatty acid isolated from leaves of wild rice (Oryza officinalis) Biosci., Biotechnol. Biochem. 1995, 59, 2049-2051
15. Mukhtarova, L. S.; Mukhitova, F. K.; Gogolev, Y. V.; Grechkin, A. N. Hydroperoxide lyase cascade in pea seedlings: non-volatile oxylipins and their age and stress dependent alterations Phytochemistry 2011, 72, 356-364
16. Griehl, W.; Ruestem, D. Nylon-12 preparation, properties and applications Ind. Eng. Chem. 1970, 62, 16-22
17. Xu, J.; Guo, B. H. Microbial Succinic Acid, Its Polymer Poly(butylene succinate), and Applications; Springer: Berlin, Germany, 2010; pp 347-388.
18. Kroha, K. Industrial biotechnology provides opportunities for commercial production of new long-chain dibasic acids INFORM-Champaign 2004, 15, 568-571
19. Otte, K. B.; Kirtz, M.; Nestl, B. M.; Hauer, B. Synthesis of 9-oxononanoic acid, a precursor for biopolymers ChemSusChem 2013, 6, 2149-2156
20. Buchhaupt, M.; Guder, J. C.; Etschmann, M. M. W.; 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
21. 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. 2013, 52, 2534-2537
22. Oh, H. Y.; Kim, S. U.; Song, J. W.; Lee, J. H.; Kang, W. R.; Jo, Y. S.; Kim, K. R.; Bornscheuer, U.; 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. 2014, 357, 408-416
23. Yu, I. S.; Yeom, S. J.; Kim, H. J.; Lee, J. K.; Kim, Y. H.; Oh, D. K. Substrate specificity of Stenotrophomonas nitritireducens in the hydroxylation of unsaturated fatty acid Appl. Microbiol. Biotechnol. 2008, 78, 157-163
24. Kim, K.-R.; Seo, M.-H.; Park, J.-B.; Oh, D.-K. Stereospecific production of 9 R -hydroxy-10 E,12 Z -octadecadienoic acid from linoleic acid by recombinant Escherichia coli cells expressing 9 R -lipoxygenase from Nostoc sp. SAG 25.82 J. Mol. Catal. B: Enzym. 2014, 104, 56-63
25. Yu, I.-S.; Kim, H.-J.; Oh, D.-K. Conversion of linoleic acid into 10-hydroxy-12(Z)-octadecenoic acid by whole cells of Stenotrophomonas nitritireducens Biotechnol. Prog. 2008, 24, 182-186
26. Voelker, A.; Kirschner, A.; Bornscheuer, U. T.; Altenbuchner, J. Functional expression, purification, and characterization of the recombinant Baeyer-Villiger monooxygenase MekA from Pseudomonas veronii MEK700 Appl. Microbiol. Biotechnol. 2008, 77, 1251-1260
27. Rehdorf, J.; Kirschner, A.; Bornscheuer, U. T. Cloning, expression and characterization of a Baeyer-Villiger monooxygenase from Pseudomonas putida KT2440 Biotechnol. Lett. 2007, 29, 1393-1398
28. Britton, L.; Markovetz, A. A novel ketone monooxygenase from Pseudomonas cepacia. Purification and properties J. Biol. Chem. 1977, 252, 8561-8566
29. Fraaije, M.; Kamerbeek, N.; Heidekamp, A.; Fortin, R.; Janssen, D. The prodrug activator EtaA from Mycobacterium tuberculosis is a Baeyer-Villiger monooxygenase J. Biol. Chem. 2004, 279, 3354-3360
30. Kirschner, A.; Altenbuchner, J.; Bornscheuer, U. T. Cloning, expression, and characterization of a Baeyer-Villiger monooxygenase from Pseudomonas fluorescens DSM 50106 in E. coli Appl. Microbiol. Biotechnol. 2007, 73, 1065-1072
31. Cho, J. Y.; Moon, J. H.; Eun, J. B.; Chung, S. J.; Park, K. H. Isolation and characterization of 3(Z)-dodecenedioic acid as an antibacterial substance from Hovenia dulcis THUNB Food Sci. Biotechnol. 2014, 13, 46-50
32. Rehdorf, J.; Mihovilovic, M. D.; Bornscheuer, U. T. Exploiting the regioselectivity of Baeyer-Villiger monooxygenases for the formation of β-amino acids and β-amino alcohols Angew. Chem. Int. Ed. 2010, 49, 4506-4508
33. Noyori, R.; Sato, T.; Kobayashi, H. Remote substituent effects in the Baeyer-Villiger oxidation. I. Through-bond γ substituent effect on the regioselectivity Tetrahedron Lett. 1980, 21, 2569-2576
34. Kockritz, A.; Martin, A. Synthesis of azelaic acid from vegetable oil-based feedstocks Eur. J. Lipid Sci. Technol. 2011, 113, 83-91
35. Zhang, F.; Huang, C. H.; Xu, T. W. Production of sebacic acid using two-phase bipolar membrane electrodialysis Ind. Eng. Chem. Res. 2009, 48, 7482-7488
36. Schmid, R. D.; Urlacher, V. Modern Biooxidation: Enzymes, Reactions and Applications; Wiley-VCH: Weinheim, Germany, 2007; pp 77-97.
37. Orru, R.; Dudek, H. M.; Martinoli, C.; Pazmino, D. E. T.; Royant, A.; Weik, M.; Fraaije, M. W.; Mattevi, A. Snapshots of enzymatic Baeyer-Villiger catalysis; oxygen activation and intermediate stabilization J. Biol. Chem. 2011, 286, 29284-29291
38. de Gonzalo, G.; Mihovilovic, M. D.; Fraaije, M. W. Recent developments in the application of Baeyer-Villiger monooxygenases as biocatalysts ChemBioChem 2010, 11, 2208-2231
39. 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, 1782-1786
40. Szolkowy, C.; Eltis, L. D.; Bruce, N. C.; Grogan, G. Insights into sequence-activity relationships amongst Baeyer-Villiger monooxygenases as revealed by the intragenomic complement of enzymes from Rhodococcus jostii RHA1 ChemBioChem 2009, 10, 1208-1217