Integrated bioprocess for the oxidation of limonene to perillic acid with Pseudomonas putida DSM 12264

Process Biochemistry - Tập 44 - Trang 764-771 - 2009
Marco Antonio Mirata1, Doreen Heerd1, Jens Schrader1
1DECHEMA e.V, Karl-Winnacker-Institut, Biochemical Engineering Group, Theodor-Heuss-Allee 25, 60486 Frankfurt, Germany

Tài liệu tham khảo

Fujita, 1993, Monoterpene glucosides and other constituents from Perilla fruteschens, Phytochemistry, 34, 1545, 10.1016/S0031-9422(00)90843-4 Krasnobajew, 1984, Terpenoids, 97 Rieks A, Kähler M, Kirchner U, Wiggenhorn K, Kinzer M, Risch S., Antimicrobial Agent Against Bacteria, Yeast and moulds. WO/2004/076400 Patent.(2004). Ezennia, 1997, Analysis of perillic acid in plasma by reversed-phase high-performance liquid chromatography with ultraviolet detection, J Chromatogr B, 688, 354, 10.1016/S0378-4347(96)00322-2 Raphael, 2003, Effect of naturally occurring monoterpenes carvone, limonene and perillic acid in the inhibition of experimental lung metastasis induced by B16F-10 melanoma cells, J Exp Clin Cancer Res, 22, 419 Yeruva, 2007, Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells, Cancer Lett, 257, 216, 10.1016/j.canlet.2007.07.020 Schrader, 2007, Microbial flavour production, 509 Wang, 1993, Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes, Tetrahedron, 49, 619, 10.1016/S0040-4020(01)86265-7 Vandamme, 2002, Bioflavours and fragrances via fermentation and biocatalysis, J Chem Technol Biotechnol, 77, 1323, 10.1002/jctb.722 Duetz, 2003, Biotransformation of limonene by bacteria, fungi, yeasts, and plants, Appl Microbiol Biotechnol, 61, 269, 10.1007/s00253-003-1221-y Lima, 2006, Oxidation of limonene catalyzed by metal (salen) complexes, Braz J Chem Eng, 23, 83, 10.1590/S0104-66322006000100009 Isken, 1998, Bacteria tolerant to organic solvents, Extremophiles, 2, 229, 10.1007/s007920050065 Sikkema, 1994, Interactions of cyclic hydrocarbons with biological membranes, J Biol Chem, 269, 8022, 10.1016/S0021-9258(17)37154-5 Speelmans, 1998, Limonene bioconversion to high concentrations of a single and stable product, perillic acid, by a solvent-resistant Pseudomonas putida strain, Appl Microbiol Biotechnol, 50, 538, 10.1007/s002530051331 Eaton, 1997, p-Cymene catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA encoding conversion of p-cymene to p-cumate, J Bacteriol, 179, 3171, 10.1128/jb.179.10.3171-3180.1997 Mars, 2001, Bioconversion of limonene to increased concentrations of perillic acid by Pseudomonas putida GS1 in a fed-batch reactor, Appl Microbiol Biotechnol, 56, 101, 10.1007/s002530100625 Freeman, 1993, In situ product removal as a tool for bioprocessing, Biotechnology, 11, 1007, 10.1038/nbt0993-1007 Stark, 2003, In situ product removal (ISPR) in whole cell biotechnology during the last twenty years, Adv Biochem Eng Biotechnol, 80, 149 Moldes, 2001, Resin selection and single-step production and recovery of lactic acid from pretreated wood, Appl Biochem Biotechnol, 95, 69, 10.1385/ABAB:95:2:069 Srivastava, 1992, Extractive lactic acid fermentation using ion-exchange resin, Biotechnol Bioeng, 39, 607, 10.1002/bit.260390604 Einicke, 1995, In-situ-Gewinnung von Fermentationsprodukten durch selective, Adsorption und Ionenaustausch Chem Technik, 47, 261 Glöcker, 1996, Industrial bioprocess for the production of substituted aromatic heterocycles, Chimia, 50, 413, 10.2533/chimia.1996.413 Kiener, 1992, Einzymatische oxidation von Methylgruppen an Heteroarenen: eine vielseitige Methode zur Herstellung heteroaromatischer Karbonsäure, Angew Chem, 104, 748, 10.1002/ange.19921040611 Cao, 1996, Simultaneous production and recovery of fumaric acid from immobilized Rhizopus oryzae with a rotary biofilm contactor and an adsorption column, Appl Environ Microbiol, 62, 2926, 10.1128/AEM.62.8.2926-2931.1996 Roddick, 1997, Production of hexanoic acid by free and immobilised cells of Megasphera elsdenii: influence of in situ product removal using ion exchange resin, J Chem Technol Biotechnol, 69, 383, 10.1002/(SICI)1097-4660(199707)69:3<383::AID-JCTB723>3.0.CO;2-H Lye, 2001, Advances in the selection and design of two-liquid phase biocatalytic reactors, 115 Lye, 1999, Application of in situ product-removal techniques to biocatalytic processes, Trends Biotechnol, 17, 395, 10.1016/S0167-7799(99)01351-7 Woodley, 2008, Future directions for in situ product removal (ISPR), J Chem Technol Biotechnol, 83, 121, 10.1002/jctb.1790 Frerichs-Deeken, 2003, Functional expression of the quinoline 2-oxidoreductase genes (qorMSL) in Pseudomonas putida KT2440 pUF1 and in P. putida 86-1 deltaqor pUF1 and analysis of the Qor proteins, Eur J Biochem, 270, 1567, 10.1046/j.1432-1033.2003.03526.x Nijkamp, 2005, The solvent-tolerant Pseudomonas putida S12 as host for the production of cinnamic acid from glucose, Appl Microbiol Biotechnol, 69, 170, 10.1007/s00253-005-1973-7 Mirata, 2008, Fungal biotransformation of (+/−)-linalool, J Agric Food Chem, 56, 3287, 10.1021/jf800099h Havilah, 1977, A micro-colorimetric method for determination of ammonia in Kjeldahl digests with a manual spectrophotometer, Lab Pract, 26, 545 Luong, 1985, Kinetics of ethanol inhibition in alcohol fermentation, Biotechnol Bioeng, 27, 280, 10.1002/bit.260270311 Fisher, 1955, Routine exchange capacity determinations of ion exchange resins, Anal Chem, 27, 1191, 10.1021/ac60103a052 Ribeiro, 2003, Modelling the adsorption kinetics of erythromycin onto neutral and anionic resins, Bioprocess Biosyst Eng, 26, 49, 10.1007/s00449-003-0324-2 Alphand, 2003, Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases, Trends Biotechnol, 21, 318, 10.1016/S0167-7799(03)00144-6 Anasthas, 2001, Adsorption of acetic acid on ion-exchange resins in non-aqueous conditions, React Funct Polym, 47, 23, 10.1016/S1381-5148(00)00066-3 Cao, 2002, Recovery of l-(+)-lactic acid by anion exchange resin Amberlite IRA-400, Biochem Eng J, 11, 186, 10.1016/S1369-703X(02)00024-4 Davison, 2004, Succinic acid adsorption from fermentation broth and regeneration, Appl Biochem Biotechnol, 113–116, 653, 10.1385/ABAB:114:1-3:653 Gluszcz, 2004, Equilibrium and dynamic investigations of organic acids adsorption onto ion-exchange resins, Bioprocess Biosyst Eng, 26, 185, 10.1007/s00449-003-0348-7 Roig, 1993, Sorption processes, 369 Viloria-Cols, 2004, Agarose-coated anion exchanger prevents cell–adsorbent interactions, J Chromatogr A, 1043, 195, 10.1016/j.chroma.2004.05.086 León, 1998, Whole-cell biocatalysis in organic media, Enzyme Microb Technol, 23, 483, 10.1016/S0141-0229(98)00078-7 Witholt, 1990, Bioconversions of aliphatic compounds by Pseudomonas oleovorans in multiphase bioreactors: background and economic potential, Trends Biotechnol, 8, 46, 10.1016/0167-7799(90)90133-I Morrish, 2008, Enhanced bioproduction of carvone in a two-liquid-phase partitioning bioreactor with a highly hydrophobic biocatalyst, Biotechnol Bioeng, 101, 768, 10.1002/bit.21941 Berger, 1999, Biotransformations in the flavor industry, 139