Abstract
Objective
To increase the production of 10S-hydroxy-8(E)-octadecenoic acid from oleic acid by whole recombinant Escherichia coli cells expressing Nostoc punctiforme 10S-dioxygenase with the aid of a chaperone.
Results
The optimal conditions for 10S-hydroxy-8(E)-octadecenoic acid production by recombinant cells co-expressing chaperone plasmid were pH 9, 35 °C, 15 % (v/v) dimethyl sulfoxide, 40 g cells l−1, and 10 g oleic acid l−1. Under these conditions, recombinant cells co-expressing chaperone plasmid produced 7.2 g 10S-hydroxy-8(E)-octadecenoic acid l−1 within 30 min, with a conversion yield of 72 % (w/w) and a volumetric productivity of 14.4 g l−1 h−1.
Conclusion
The activity of recombinant cells expressing 10S-dioxygenase was increased by 200 % with the aid of a chaperone, demonstrating the first biotechnological production of 10S-hydroxy-8(E)-octadecenoic acid using recombinant cells expressing 10S-dioxygenase.
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References
Bódalo A, Bastida J, Máximo M, Hidalgo A, Murcia M (2005) Production of (E)10-hydroxy-8-octadecenoic acid with lyophilized microbial cells. Am J Biochem Biotechnol 1:1–4
Brash AR, Niraula NP, Boeglin WE, Mashhadi Z (2014) An ancient relative of cyclooxygenase in cyanobacteria is a linoleate 10S-dioxygenase that works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity. J Biol Chem 289:13101–13111
Culleré J, Durany O, Busquets M, Manresa A (2001) Biotransformation of oleic acid into (E)-10-hydroxy-8-octadecenoic acid and (E)-7,10-dihydroxy-8-octadecenoic acid by Pseudomonas sp. 42A2 in an immobilized system. Biotechnol Lett 23:215–219
Han JE, Seo MJ, Shin KC, Oh DK (2016) Production of 10R-hydroxy unsaturated fatty acids from hempseed oil hydrolyzate by recombinant Escherichia coli cells expressing PpoC from Aspergillus nidulans. Appl Microbiol Biotechnol. doi:10.1007/s00253-00016-07508-00256
Hou CT (2000) Biotransformation of unsaturated fatty acids to industrial products. Adv Appl Microbiol 47:201–220
Kim KR, Oh DK (2013) Production of hydroxy fatty acids by microbial fatty acid-hydroxylation enzymes. Biotechnol Adv 31:1473–1485
Kuo TM, Huang JK, Labeda D, Wen L, Knothe G (2008) Production of 10-hydroxy-8(E)-octadecenoic acid from oleic acid conversion by strains of Pseudomonas aeruginosa. Curr Microbiol 57:437–441
Liberek K, Lewandowska A, Zietkiewicz S (2008) Chaperones in control of protein disaggregation. EMBO J 27:328–335
Marasco EK, Vay K, Schmidt-Dannert C (2006) Identification of carotenoid cleavage dioxygenases from Nostoc sp. PCC 7120 with different cleavage activities. J Biol Chem 281:31583–31593
Martin-Arjol I, Busquets M, Manresa A (2013) Production of 10(S)-hydroxy-8(E)-octadecenoic acid mono-estolides by lipases in non-aqueous media. Proc Biochem 48:224–230
Nishihara K, Kanemori M, Kitagawa M, Yanagi H, Yura T (1998) Chaperone co-expression plasmids: differential and synergistic roles of DnaK-DnaJ-GrpE and GroEL-GroES in assisting folding of an allergen of Japanese cedar pollen, Cryj2, in Escherichia coli. Appl Environ Microbiol 64:1694–1699
Oliw EH, Su C, Skogström 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 33:843–852
Seo MJ, Shin KC, Oh DK (2014) Production of 5,8-dihydroxy-9,12(Z, Z)-octadecadienoic acid from linoleic acid by whole recombinant Escherichia coli cells expressing diol synthase from Aspergillus nidulans. Appl Microbiol Biotechnol 98:7447–7456
Sim DH, Shin KC, Oh DK (2015) 13-Hydroxy-9Z,11E-octadecadienoic acid production by recombinant cells expressing Burkholderia thailandensis 13-lipoxygenase. J Am Oil Chem Soc 92:1259–1266
Zheng CJ, Yoo JS, Lee TG, Cho HY, Kim YH, Kim WG (2005) Fatty acid synthesis is a target for antibacterial activity of unsaturated fatty acids. FEBS Lett 579:5157–5162
Acknowledgments
This study was supported by a grant from the Korea Healthcare Technology R&D Project, Ministry for Health & Welfare, Republic of Korea (No. 2012-009).
Supporting information
Supplementary Fig. 1—LC–MS/MS spectra for the products obtained from the conversion of unsaturated fatty acids to 10S-hydroxy fatty acids by recombinant cells expressing 10S-dioxygenase from N. punctiforme PCC 73102.
Supplementary Fig. 2—Effects of pH and temperature on the conversion of oleic acid to 10S-hydroxy-8(E)-octadecenoic acid by recombinant cells co-expressing the 10S-dioxygenase gene of N. punctiforme with pGro7.
Supplementary Fig. 3—Effect of dimethyl sulfoxide concentration on the conversion of oleic acid to 10S-hydroxy-8(E)-octadecenoic acid by recombinant cells co-expressing the 10S-dioxygenase gene of N. punctiforme with pGro7.
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Kim, MJ., Seo, MJ., Shin, KC. et al. Production of 10S-hydroxy-8(E)-octadecenoic acid from oleic acid by whole recombinant Escherichia coli cells expressing 10S-dioxygenase from Nostoc punctiforme PCC 73102 with the aid of a chaperone. Biotechnol Lett 39, 133–139 (2017). https://doi.org/10.1007/s10529-016-2225-x
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DOI: https://doi.org/10.1007/s10529-016-2225-x