Production of 5,8-dihydroxy-9,12(Z,Z)-octadecadienoic acid from linoleic acid by whole recombinant Escherichia coli cells expressing diol synthase from
详细信息 查看全文
- 作者：Min-Ju Seo (1)
Kyung-Chul Shin (1)
Deok-Kun Oh (1) - 关键词：Aspergillus nidulans ; Linoleic acid ; 5 ; 8 ; Dihydroxy ; 9 ; 12(Z ; Z) ; octadecadienoic acid production ; Diol synthase ; Recombinant Escherichia coli
- 刊名：Applied Microbiology and Biotechnology
- 出版年：2014
- 出版时间：September 2014
- 年：2014
- 卷：98
- 期：17
- 页码：7447-7456
- 全文大小：420 KB
- 参考文献：1. Back KY, Sohn HR, Hou CT, Kim HR (2011) Production of a novel 9,12-dihydroxy-10( / E)-eicosenoic acid from eicosenoic acid by / Pseudomonas aeruginosa PR3. J Agric Food Chem 59:9652-657 CrossRef
2. Bae JH, Suh MJ, Kim BS, Hou CT, Lee IJ, Kim IH, Kim HR (2010) Optimal production of 7,10-dihydroxy-8( / E)-hexadecenoic acid from palmitoleic acid by / Pseudomonas aeruginosa PR3. N Biotechnol 27:352-57 CrossRef
3. Brodhun F, Gobel C, Hornung E, Feussner I (2009) Identification of PpoA from / Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450. J Biol Chem 284:11792-1805 CrossRef
4. Brodowsky I, Hamberg M, Oliw E (1992) A linoleic acid (8 / R)-dioxygenase and hydroperoxide isomerase of the fungus / Gaeumannomyces graminis. Biosynthesis of (8 / R)-hydroxylinoleic acid and (7 / S, 8 / S)-dihydroxylinoleic acid from (8 / R)-hydroperoxylinoleic acid. J Biol Chem 267:14738-4745
5. Chen TC, Ju YH (2001) An improved fractional crystallization method for the enrichment of γ-linolenic acid in borage oil fatty acid. Ind Eng Chem Res 40:3781-784 CrossRef
6. Cristea M, Osbourn AE, Oliw EH (2003) Linoleate diol synthase of the rice blast fungus / Magnaporthe grisea. Lipids 38:1275-280 CrossRef
7. Fox SR, Akpinar A, Prabhune AA, Friend J, Ratledge C (2000) The biosynthesis of oxylipins of linoleic and arachidonic acids by the sewage fungus / Leptomitus lacteus, including the identification of 8 / R-hydroxy-9 / Z,12 / Z-octadecadienoic acid. Lipids 35:23-0 CrossRef
8. Garscha U, Jerneren F, Chung D, Keller NP, Hamberg M, Oliw EH (2007) Identification of dioxygenases required for / Aspergillus development studies of products, stereochemistry, and the reaction mechanism. J Biol Chem 282:34707-4718 CrossRef
9. Gibson DG, Young L, Chuang RY, Venter JC, Hutchison CA, Smith HO (2009) Enzymatic assembly of DNA molecules up to several hundred kilobases. Nat Methods 6:343-45 CrossRef
10. Hoffmann I, Jerneren F, Garscha U, Oliw EH (2011) Expression of 5,8-LDS of / Aspergillus fumigatus and its dioxygenase domain. A comparison with 7,8-LDS, 10-dioxygenase, and cyclooxygenase. Arch Biochem Biophys 506:216-22 CrossRef
11. Hoffmann I, Jerneren F, Oliw EH (2013) Expression of fusion proteins of / Aspergillus terreus reveals a novel allene oxide synthase. J Biol Chem 288:11459-1469 CrossRef
12. Hoffmann I, Oliw EH (2013) Discovery of a linoleate 9 / S-dioxygenase and an allene oxide synthase in a fusion protein of / Fusarium oxysporum. J Lipid Res 54:3471-480 CrossRef
13. Hou CT (2005) Effect of environmental factors on the production of oxygenated unsaturated fatty acids from linoleic acids by / Bacillus megaterium ALA2. Appl Microbiol Biotechnol 69:463-68 CrossRef
14. Hou CT (2008) New bioactive fatty acids. Asia Pac J Clin Nutr 17(Suppl 1):192-95
15. Hou CT (2009) Biotechnology for fats and oils: new oxygenated fatty acids. N Biotechnol 26:2-0 CrossRef
16. Jerneren F, Garscha U, Hoffmann I, Hamberg M, Oliw EH (2010) Reaction mechanism of 5,8-linoleate diol synthase, 10 / R-dioxygenase, and 8,11-hydroperoxide isomerase of / Aspergillus clavatus. Biochim Biophys Acta 1801:503-07 CrossRef
17. Kim H, Kuo TM, Hou CT (2000) Production of 10,12-dihydroxy-8( / E)-octadecenoic acid, an intermediate in the conversion of ricinoleic acid to 7,10,12-trihydroxy-8( / E)-octadecenoic acid by / Pseudomonas aeruginosa PR3. J Ind Microbiol 24:167-72 CrossRef
18. Kuo TM, Manthey LK, Hou CT (1998) Fatty acid bioconversions by / Pseudomonas aeruginosa PR3. J Am Oil Chem Soc 75:857-59 CrossRef
19. Martinez E, Hamberg M, Busquets M, Diaz P, Manresa A, Oliw EH (2010) Biochemical characterization of the oxygenation of unsaturated fatty acids by the dioxygenase and hydroperoxide isomerase of / Pseudomonas aeruginosa 42A2. J Biol Chem 285:9339-345 CrossRef
20. Morris LJ (1968) Fatty acid composition of / Claviceps species. Occurrence of (+)-threo-9, 10-dihydroxystearic acid. Lipids 3:260-61 CrossRef
21. Notman R, den Otter WK, Noro MG, Briels WJ, Anwar J (2007) The permeability enhancing mechanism of DMSO in ceramide bilayers simulated by molecular dynamics. Biophys J 93:2056-068 CrossRef
22. Oliw EH, Su C, Skogstrom T, Benthin G (1998) Analysis of novel hydroperoxides and other metabolites of oleic, linoleic, and linolenic acids by liquid chromatography-mass spectrometry with ion trap MSn. Lipids 33:843-52 CrossRef
23. Parra JLPJ, Comelles F, Manresa MA, Bosch MP (1990) Studies of biosurfactants obtained from olive oil. Tenside Surf Det 27:302-06
24. Romero-Guido C, Belo I, Ta TM, Cao-Hoang L, Alchihab M, Gomes N, Thonart P, Teixeira JA, Destain J, Wache Y (2011) Biochemistry of lactone formation in yeast and fungi and its utilisation for the production of flavour and fragrance compounds. Appl Microbiol Biotechnol 89:535-47 CrossRef
25. Seo MH, Kim KR, Oh DK (2013) Production of a novel compound, 10,12-dihydroxystearic acid from ricinoleic acid by an oleate hydratase from / Lysinibacillus fusiformis. Appl Microbiol Biotechnol 97:8987-995 CrossRef
26. Su C, Oliw EH (1996) Purification and characterization of linoleate 8-dioxygenase from the fungus / Gaeumannomyces graminis as a novel hemoprotein. J Biol Chem 271:14112-4118 CrossRef
27. Wadman MW, de Vries RP, Kalkhove SI, Veldink GA, Vliegenthart JF (2009) Characterization of oxylipins and dioxygenase genes in the asexual fungus / Aspergillus niger. BMC Microbiol 9:59 CrossRef
28. Wadman MW, van Zadelhoff G, Hamberg M, Visser T, Veldink GA, Vliegenthart JF (2005) Conversion of linoleic acid into novel oxylipins by the mushroom / Agaricus bisporus. Lipids 40:1163-170 CrossRef - 作者单位：Min-Ju Seo (1)
Kyung-Chul Shin (1)
Deok-Kun Oh (1)
1. Department of Bioscience and Biotechnology, Konkuk University, Seoul, 143-701, South Korea - ISSN：1432-0614
文摘
Diol synthase from Aspergillus nidulans was cloned and expressed in Escherichia coli. Recombinant E. coli cells expressing diol synthase from A. nidulans converted linoleic acid to a product that was identified as 5,8-dihydroxy-9,12(Z,Z)-octadecadienoic acid by liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS). The recombinant cells and the purified enzyme showed the highest activity for linoleic acid among the fatty acids tested. The optimal reaction conditions for the production of 5,8-dihydroxy-9,12(Z,Z)-octadecadienoic acid from linoleic acid using whole recombinant E. coli cells expressing diol synthase were pH 7.5, 35°C, 250 rpm, 5 g l? linoleic acid, 23 g l? cells, and 20% (v/v) dimethyl sulfoxide in a 250-ml baffled flask. Under these optimized conditions, whole recombinant cells expressing diol synthase produced 4.98 g l? 5,8-dihydroxy-9,12(Z,Z)-octadecadienoic acid for 150 min without detectable byproducts, with a conversion yield of 99% (w/w) and a productivity of 2.5 g l? h?. This is the first report on the biotechnological production of dihydroxy fatty acid using whole recombinant cells expressing diol synthase.