Abstract
Recombinant Escherichia coli whole-cell biocatalysts harboring either a Baeyer–Villiger monooxygenase or ferulic acid decarboxylase were employed in organic-aqueous two-phase bioreactor systems. The feasibility of the bioproduction of water-insoluble products, viz., lauryl lactone from cyclododecanone and 4-vinyl guaiacol from ferulic acid were examined. Using hexadecane as the organic phase, 10∼16 g of lauryl lactone were produced in a 3-l bioreactor that operated in a semicontinuous mode compared to 2.4 g of product in a batch mode. For the decarboxylation of ferulic acid, a new recombinant biocatalyst, ferulic acid decarboxylase derived from Bacillus pumilus, was constructed. Selected solvents as well as other parameters for in situ recovery of vinyl guaiacol were investigated. Up to 13.8 g vinyl guaiacol (purity of 98.4%) were obtained from 25 g of ferulic acid in a 2-l working volume bioreactor by using octane as organic phase. These selected examples highlight the superiority of the two-phase biotransformations systems over the conventional batch mode.
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Baldwin CVF, Woodley JM (2006) On oxygen limitation in a whole cell biocatalytic Baeyer–Villiger oxidation process. Biotechnol Bioeng 95:362–369
Barthelmebs L, Diviès C, Cavin J-F (2001) Expression in Escherichia coli of native and chimeric phenolic acid decarboxylases with modified enzymatic activities and method for screening recombinant E. coli strains expressing these enzymes. Appl Environ Microbiol 67:1063–1069
Beneventi E, Ottolina G, Carrea G, Panzeri W, Fronza G, Lau PCK (2009) Enzymatic Baeyer–Villiger oxidation of steroids with cyclopentadecanone monooxygenase. J Mol Catal B: Enzym 58:164–168
Bernini R, Mincione E, Barontini M, Provenzano G, Setti L (2007) Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation. Tetrahedron 63:9663–9667
Brosius J (1984) Plasmid vectors for the selection of promoters. Gene 27:151–160
Buhler B, Schmid A (2004) Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization. J Biotechnol 113:183–210
Caesar B (2008) More than just ethanol–Factors driving industry growth. Ind Biotechnol 4:50–54
Cavin J-F, Barthelmebs L, Diviès C (1997) Molecular characterization of an inducible p-coumaric acid decarboxylase from Lactobacillus plantarum: gene cloning, transcriptional analysis, overexpression in Escherichia coli, purification, and characterization. Appl Environ Microbiol 63:1939–1944
Cavin J-F, Dartois V, Diviès C (1998) Gene cloning, transcriptional analysis, purification, and characterization of phenolic aicd decarboxylase from Bacillus subtilis. Appl Environ Microbiol 64:1466–1471
Constable DJC, Dunn PJ, Hayler JD, Humphrey GR, LeazerJr JL, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY (2007) Key green chemistry research areas - a perspective from pharmaceutical manufacturers. Green Chem 9:411–420
Daugulis AJ (2001) Two-phase partitioning bioreactors: a new technology platform for destroying xenobiotics. Trends Biotechnol 19:457–462
Deziel E, Comeau Y, Villemur R (1999) Two-liquid-phase bioreactors for enhanced degradation of hydrophobic /toxic compounds. Biodegradation 10:219–233
Doig SD, O' Sullivan LM, Patel S, Ward JM, Woodley JM (2001) Large scale production of cyclohexanone monooxygenase from Escherichia coli TOP10 pQR239. Enzyme Microb Technol 28:265–274
Gennaro PD, Ferrara S, Bestetti G, Sello G, Solera D, Galli E, Renzi F, Bertoni G (2008) Novel auto-inducing expression systems for the development of whole-cell biocatalysts. Appl Microbiol Biotechnol 79:617–625
Griengl H, Appenroth M, Dax K, Schwarz H (1969) Zur Umsetzung von Formaldehyd mit Hydroxystyrolen in alkalischem Medium. Monatsh Chem 100:316–327
Hatakeyama H, Hayashi E, Haraguchi T (1977) Biodegradation of poly(3-methoxy-4-hydroxystyrene). Polym 18:759–763
Heipieper H, Neumann G, Cornelissen S, Meinhardt F (2007) Solvent-tolerant bacteria for biotransformations in two-phase fermentation systems. Appl Microbiol Biotechnol 74:961–973
Hermann BG, Patel M (2007) Producing bio-based bulk chemicals using industrial biotechnology saves energy and combats climate change. Environ Sci Technol 41:7915–7921
Hilker I, Alphand W, Wohlgemuth R, Furstoss R (2004a) Microbial transformations, 56. Preparative scale asymmetric Baeyer–Villiger oxidation using a highly productive "two-in-one" resin-based in situ SFPR concept. Adv Synth Catal 346:203–214
Hilker I, Gutiérrez MC, Alphand V, Wohlgemuth R, Furstoss R (2004b) Microbiological transformations 57. Facile and efficient resin-based in situ SFPR preparative-scale synthesis of an enantiopure “unexpected” lactone regioisomer via a Baeyer−Villiger oxidation process. Org Lett 6:1955–1958
Hilker I, Wohlgemuth R, Alphand V, Furstoss R (2005) Microbial transformations 59: First kilogram scale asymmetric microbial Baeyer–Villiger oxidation with optimized productivity using a resin-based in situ SFPR strategy. Biotechnol Bioeng 92:702–710
Hilker I, Gutiérrez MC, Furstoss R, Ward J, Wohlgemuth R, Alphand V (2008) Preparative scale Baeyer–Villiger biooxidation at high concentration using recombinant Escherichia coli and in situ substrate feeding and product removal process. Nat Protocol 3:546–554
Huang Z, Dostal L, Rosazza JPN (1993) Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Appl Environ Microbiol 59:2244–2250
Huang Z, Dostal L, Rosazza JPN (1994) Purification and characterization of ferulic acid decarboxylase from Pseudomonas fluorescens. J Bacteriol 176:5912–5918
Ikeda I, Washino K, Maeda Y (2003) Graft polymerization of cyclic compounds on cellulose dissolved in tertabutylammonium fluoride /dimethyl sulfoxide. Fiber 59:110–114
Iwaki H, Wang S, Grosse S, Bergeron H, Nagahashi A, Lertvorachon J, Yang J, Konishi Y, Hasegawa Y, Lau PCK (2006) Pseudomonad cyclopentadecanone monooxygenase displaying an uncommon spectrum of Baeyer–Villiger oxidations of cyclic ketones. Appl Environ Microbiol 72:2707–2720
Jeong PY, Jung M, Yim YH, Kim H, Park M, Hong E, Lee W, Kim YH, Kim K, Paik YK (2005) Chemical structure and biological activity of the Caenorhabditis elegans dauer-inducing pheromone. Nat 433:541–545
Kim P-Y, Pollard DJ, Woodley JM (2007) Substrate supply for effective biocatalysis. Biotechnol Prog 23:74–82
Lee IY, Volm TG, Rosazza JPN (1998) Decarboxylation of ferulic acid to 4-vinylguaiacol by Bacillus pumilus in aqueous-organic solvent two-phase systems. Enzyme Microb Technol 23:261–266
Lee W-H, Park J-B, Park K, Kim M-D, Seo J-H (2007) Enhanced production of ε-caprolactone by overexpression of NADPH-regenerating glucose 6-phosphate dehydrogenase in recombinant Escherichia coli harboring cyclohexanone monooxygenase gene. Appl Microbiol Biotechnol 76:329–338
Malinowski JJ (2001) Two-phase partitioning bioreactors in fermentation technology. Biotechnol Adv 19:525–538
Mathew S, Abraham TE (2004) Ferulic acid: An antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications. Crit Rev Biotechnol 24:59–83
Mathew S, Abraham TE (2006) Bioconversions of ferulic acid, a hydroxycinnamic acid. Crit Rev Microbiol 33:115–125
Muñoz R, Villaverde S, Guieysse B, Revah S (2007) Two-phase partitioning bioreactors for treatment of volatile organic compounds. Biotechnol Adv 25:410–422
Nomura E, Hosoda A, Mori H, Taniguchi H (2005) Rapid base-catalyzed decarboxylation and amide-forming reaction of substituted cinnamic acids via microwave heating. Appl Microbiol Biotechnol 7:863–866
Panke S, Held M, Wubbolts MG, Witholt B, Schmid A (2002) Pilot-scale production of (S)-styrene oxide from styrene by recombinant Escherichia coli synthesizing styrene monooxygenase. Biotechnol Bioeng 81:33–41
Prim N, Pastor F, Diaz P (2003) Biochemical studies on cloned Bacillus sp. BP-7 phenolic acid decarboxylase PadA. Appl Microbiol Biotechnol 63:61–56
Rodriguez H, Landete JM, Curiel JA, DelasRivas B, Mancheño JM, Muñoz R (2008) Characterization of the p-coumaric acid decarboxylase from Lactobacillus plantarum CECT 748T. J Agric Food Chem 56:3068–3072
Rosazza JPN, Huang Z, Dostal L, Volm T, Rousseau B (1995) Review: Biocatalytic transformations of ferulic acid: An abundant aromatic natural product. J Ind Microbiol 15:457–471
Sambrook JE, Fritsch EF, Maniatis T (1989) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York
Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B (2001) Industrial biocatalysis today and tomorrow. Nature 409:258–268
Schumacher JD, Fakoussa RM (1999) Degradation of alicyclic molecules by Rhodococcus ruber CD4. Appl Microbiol Biotechnol 52:85–90
Staijen IE, van Beilen JB, Witholt B (2000) Expression, stability and performance of the three-component alkane mono-oxygenase of Pseudomonas oleovorans in Escherichia coli. Eur J Biochem 267:1957–1965
ten Brink G-J, Arends IWCE, Sheldon RA (2004) The Baeyer−Villiger reaction: New developments toward greener procedures. Chem Rev 104:4105–4123
Thomas SM, DiCosimo R, Nagarajan V (2002) Biocatalysis: applications and potentials for the chemical industry. Trends Biotechnol 20:238–242
Tsujiyama S-I, Ueno M (2008) Formation of 4-vinyl guaiacol as an intermediate in bioconversion of ferulic acid by Schizophyllum commune. Biosci Biotechnol Biochem 72:212–215
Walton AZ, Stewart JD (2002) An efficient enzymatic Baeyer–Villiger oxidation by engineered Escherichia coli cells under non-growing conditions. Biotechnol Prog 18:262–268
Warth H, Mulhaupt R, Schatzle J (1997) Thermoplastic cellulose acetate and cellulose acetate compounds prepared by reactive processing. Appl Poly Sci 64:231–242
Woodley JM (2008) New opportunities for biocatalysis: making pharmaceutical processes greener. Trends Biotechnol 26:321–327
Yang J, Lorrain M-J, Rho D, Lau PCK (2006) Monitoring of Baeyer–Villiger biotransformation kinetics and fingerprinting using ReactIR 4000 spectroscopy. Ind Biotechnol 2:138–142
Zago A, Degrassi G, Bruschi CV (1995) Cloning, sequencing, and expression in Escherichia coli of the Bacillus pumilus gene for ferulic acid decarboxylase. Appl Environ Microbiol 61:4484–4486
Acknowledgements
We thank the Climate Change Technology and Innovation Biotechnology Program of the Canadian Biomass Innovation Network of Natural Resources Canada for financial support. We are grateful to H. Leisch for suggestions and help with the manuscript.
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Yang, J., Wang, S., Lorrain, MJ. et al. Bioproduction of lauryl lactone and 4-vinyl guaiacol as value-added chemicals in two-phase biotransformation systems. Appl Microbiol Biotechnol 84, 867–876 (2009). https://doi.org/10.1007/s00253-009-2026-4
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DOI: https://doi.org/10.1007/s00253-009-2026-4