Abstract
Biotransformation can be defined as a process dealing with the conversion of a compound, often called precursor, into structurally related compound(s) by a biocatalyst in a limited number of enzymatic steps. Such operation is also called microbial transformation or even bioconversion. Straathof et al (2002) thus define biotransformation as “a reaction or a set of simultaneous reactions in which a pre-formed precursor molecule is converted, in contrast to a fermentation process with de novo production from a carbon and energy source such as glucose via primary metabolism”. The biocatalyst can be whole cells, spores, crude enzymes or purified enzymes.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Abraham WR, Arfman HA, Stumpf B, Washington P & Kieslich K, 1988, Microbial transformation of some terpenoids and natural compounds, Bioflavour 87, Proceedings of the International Conference, 399–414
Adams A, Demyttenaere JCR & de Kimpe R, 2003, Biotransformation of (R)-(+)- and (S)-(-)-limonene to α-terpineol by Penicillium digitatum - investigation of the culture conditions, Food Chemistry, 80, 525–534
Asano Y, 2002, Overview of screening for new microbial catalysts and their uses in organic synthesis—selection and optimization of biocatalysts, Journal of Biotechnology, 94, 65–72
Babicka J & Volf J, 1955, Czechoslovak Patent 84 320
Bais HP, Sudha G, Suresh B & Ravishankar GA, 2001, Permeabilization and in situ adsorption studies during growth and coumarin production in hairy root cultures of Cichorium intybus L. Indian Journal of Experimental Biology, 39, 564–571
Berger RG, 1995, Biotransformation/Bioconversion, In- Aroma biotechnology, Springer-Verlag, Berlin, Heidelberg, New York, pp 79–91
Berger RG, de Boot JAM, Eggink G, da Fonseca M, Gehrke M, Gros JB, van Keulen F, Krings U, Larroche C, Leak DJ & van der Werf M, 1999, Biotransformations in the flavour industry. In- Current Topics in flavours and fragrances, KAD Swift (ed), Kluwer Academic Publishers, Dordrecht, pp 139–170
Best DJ, Floyd NC, Magalhaes A, Burfield A & Rhodes PM, 1987, Initial enzymatic steps in the degradation of alpha-pinene by Pseudomonas fluorescens NCIMB 11671, Biocatalysis, 1, 147–159
Bhattacharyya PK & Ganapathy K, 1965, Microbiological tranformation of terpenes, part VI: Studies on the mechanism of some fungal hydroxylation reactions with the aid of model systems, Indian Journal of Biochemistry, 2, 137
Brennecke JF & Maginn EJ, 2001, Ionic liquids: innovative fluids for chemical processing. AIChE Journal, 47, 2384–2389
Bucke C, 1883, Immobilized cells, Philosophic Transactions of the Royal Society of London, B300, 369–389
Burfield AG, Best DJ & Davis KJ, 1989, Production of 2-methyl-5isopropylhexa-2,5-dien-l-al and of 2-methyl-5-isopropyl-hexa-2,4-dien-l-al in microorganisms, European Patent 0 304 318
Cabral J.M.S. (2001). Biotransformation. In. Basic Biotechnology, 2nd edition, Ratledge C., Kristiansen B. (eds), Cambridge University Press, Cambridge, pp 471–501
Cadwallader KR, Braddock RJ, Parish ME & Higgins DP, 1989, Bioconversion of (+)-limonene by Pseudomonas gladioli, Journal of Food Science, 54, 1241–1245
Champagne CP, Lacroix C & Dodini-Gallot I, 1994, Immobilized cell technologies for industries. Critical Reviews in Biotechnology, 14, 109–134
Chang HC, Cage DA & Oriel PJ, 1995, Cloning and expression of a limonene degradation pathway from Bacillus stearothermophilus in Escherichia coli. Journal of Food Science, 60, 551–553
ChatterjeeT & Bhattacharyya DK, 2001, Biotransformation of limonene by Pseudomonas putida, Applied Microbiology and Biotechnology, 55, 541–546
Colocousi A, Saqib KM & Leak DJ, 1996, Mutants of Pseudomonas fluorescens NCIMB 11671 defective in the catabolism of α-pinene, Applied Microbiology and Biotechnology, 45, 822–830
Crameri A, Raillard SA, Bermudez E & Stemmer WP, 1998, DNA shuffling of a family of genes from diverse species accelerates directed evolution, Nature, 15, 391, 288–91
Demirjian DC, Morís-Varas F & Cassidy CS, 2001, Enzymes from extremophiles, Current Opinion in Chemical Biology, 5, 144–151
Demyttenaere JCR & de Pooter HL, 1998, Biotransformation of citral and nerol by spores of Penicillium digitatum, Flavour and Fragrance Journal, 13, 173–176
Demyttenaere JCR, del Carmen Herrera M & de Kimpe N, 2000, Biotransformation of geraniol, nerol and citral by sporulated surface cultures of Aspergillus niger and Penicillium sp., Phytochemistry, 55, 363–373
Dhavalikar RS & Bhattacharyya PK, 1966, Microbial transformations of terpenes: Part VIII- Fermentation of limonene in a soil pseudomonad, Indian Journal of Biochemistry, 3, 144–157
Dhavalikar RS, Rangachari PN & Bhattacharyya PK, 1966, Microbial transformations of terpenes: Part IX-pathways of limonene degradation by a soil pseudomonad, Indian Journal of Biochemistry, 3, 158–164
Divies C, Cachon R, Cavin JF & Prevost H, 1994, Theme 4: immobilized cell technology in wine production, Critical Reviews in Biotechnology, 14, 135–153
Draczynska B, Cagara CZ, Siewinski A, Rymkiewicz A, Zabza A & Leufven A, 1985, Biotransformation of pinenes XVII. Transformation of α- and β-pinenes by means of Armillariella mellae (honey fungus), a parasite of woodlands. Journal of Basic Microbiology, 8, 487–492
Duetz WA, Bouwmeester H, van Bellen JB & Witholt B, 2003, Biotransformation of limonene by bacteria, fungi, yeasts, and plants, Applied Microbiology and Biotechnology, 61, 269–77
Duetz WA, van Beilen JB & Witholt B, 2001a, Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis, Current Opinion in Biotechnology, 12, 419–25
Duetz WA, Jourdat C & Witholt B, 2001b, Process for the preparation of perillyl alcohol. European Patent EP1236802
Engesser K-H & Plaggemeier T, 2000, Microbiological aspects of biological waste gas purification, In Biotechnology, 2nd edition, H-J Rehm, G. Reed (eds), vol. 11c, Wiley-VCH, Weinhain, pp 275–302
Entzeroth M, 2003, Emerging trends in high-throughput screening, Current Opinion in Pharmacology, 3, 522–529
Erbeldinger M, Mesiano AJ & Russell AJ, 2000, Enzymatic catalysis of formation of Z-aspartame in ionic liquid - an alternative to enzymatic catalysis in organic solvents, Biotechnology Progress, 16, 1129–1131
Felix H, 1982, Permeabilized cells, Analytical Biochemistry, 120, 211–234
Fernandes P, Cruz A, Angelova B, Pinheiro HM & Cabral JMS, 2003, Microbial conversion of steroid compounds: recent developments, In- Enzyme and Microbial Technology, Volume 32, pp 688–705
Ferrer P, Hedegaard L, Halkier T, Diers I, Savva D & Asenjo JA, 1996, Molecular cloning of a lytic β-l,3-glucanase gene from Derskovia xanthineolytica LLG109: a β-1,3-glucanase able to selectively permeabilize the yeast cell wall, Annals of New-York Academy of Sciences, 782, 555–565
Firestine SM, Salinas F, Nixon AE, Baker SJ & Benkovic SJ, 2000, Using an AraC-based three-hybrid system to detect biocatalysts in vivo, Nat. Biotechnol, 18, 544–547
Fontanille P & Larroche C, 2002, Pseudomonas rhodesiae sp.: a new and efficient biocatalyst for production of isonovalal from α-pinene oxide, Biocatalysis and Biotransformation, 20, 413–421
Fontanille P & Larroche C, 2003, Optimisation of isonovalal production from α-pinene oxide using permeabilized cells of Pseudomonas rhodesiae CIP 107491, Applied Microbiology and Biotechnology, 60, 534–540
Freire AP, Martins AM & Cordeiro C, 1998, A practical experiment on cell permeabilization and biochemical characterization in situ, Biochemical Education, 26, 66–68
Galabova D, Tuleva B & Spasova D, 1996, Permeabilization of Yarrowia lipolytica cells by Triton X-100, Enzyme Microbiology and Technology, 18, 18–22
Gibbon GH & Pirt SJ, 1971, Dégradation of α-pinene by Pseudomonas PX1, FEBS Letters, 18, 103–105
Greenbaum D, Medzihradszky KF, Burlingame A & Bogyo M, 2000, Epoxide electrophiles as activity-dependent cysteine protease profiling and discovery tools, Chemical Biology, 7, 569–581
Griffith KL & Wolf RE Jr, 2002, Measuring β-galactosidase activity in bacteria: cell growth, permeabilization, and enzyme essay in 96-well arrays, Biochemical and Biophysical Research Communication, 290, 397–402
Griffiths ET, Bociek SM, Harries PC, Jeffcoat R, Sissous DJ & Trugdill PW, 1987a, Bacterial metabolism of α-pinene: pathway from α-pinene oxide to acyclic metabolites in Norcadia sp. strain P18.3, Journal of Bacteriology, 169, 4972–4979
Griffiths ET, Harries PC, Jeffcoat R & Trugdill PW, 1987b, Purification and properties of α-pinene oxide lyase from Norcadia sp. Strain P18.3, Journal of Bacteriology, 169, 4980–4983
Grivel F & Larroche C, 2001, Phase transfer and biocatalyst behaviour during biotransformation of β-ionone in a two phase liquid system by immobilised Aspergillus niger, Biochemical Engeneering Journal, 7, 27–34
Grivel F, Larroche C & Gros JB, 1999, Determination of the reaction yield during biotransformation of the volatile and chemically unstable compound β-ionone by Aspergillus niger, Biotechnology Progress, 15, 697–705
Groboillot A, Boadi DK, Poncelet D & Neufeld RJ, 1994, Immobilization of cells for application in the food industry, Critical Reviews in Biotechnology, 14, 75–107
Gros JB, Larroche C & Detest P, 1996, Preparation de pyrazines par bioconversion, French Patent 2728913
Harayama S, Kok M & Niedle EL, 1992, Functional and evolutionary relationships among diverse oxygenases, Annual Review of Microbiology, 46, 565–601
Harries PC, Jeffcoat R, Griffiths ET & Trudgill PW, 1989, Monoterpene aldehyde or alcohol derivatives and their use as perfumes or flavouring agents, European patent EP86202335.5
Hartmeier W, 1985, Immobilized biocatalyst- from simple to complex systems, Trends in Biotechnology, 3, 149–153
Hasekawa Co, 1972, Japanese Patent 7 238 998
Holwarth A, Schmidt H-W & Maier WF, 1998, Detection of catalytic activity in combinatorial libraries of heterogeneous catalysts by using capillary array electrophoresis, Angewandte Chemie, International Edition in English, 37, 2644–2647
Howarth J, James P & Dai J, 2001, Immobilized baker’s yeast reduction ofketones in an ionic liquid, [bmim] PF6 and water mix, Tetrahedron Letters, 42, 7517–7519
Jackson RW & Demoss JA, 1965, Effect of toluene on Escherichia coli, Journal of Bacteriololgy, 90, 1420–1425
Johnson BH & Hecht MH, 1994, Recombinant proteins can be isolated from Escherichia coli by repeated cycles of freezing and thawing, Bio/Technology, 12, 1357–1360
Katsuragi T & Tani Y, 2000, Screening for microorganisms with specific characteristics by flow cytometry and single-cell sorting, Journal of Biosciences and Bioengineering, 89, 217–222
Kelly DR, 1998, Biotransformation - Practical aspects, In- Biotechnology, vol 8a, DR Kelly (ed), VCH-Wiley, Weinheim, pp 25–34
Kieslich K, 1976, Terpenoids, In- Microbial Transformation of Non-steroid Cyclic Compounds, Georg Thieme Verlag, Stuttgart, 56–84
Kleinheinz GT & Bagley ST, 1997, A filter-plate method for the recovery and cultivation of microorganisms utilizing volatile organic compounds, Journal of Microbiological Methods, 29, 139–144
Krasnobajew V, 1984, Terpenoids, In- Biotechnology, Kieslich K. (ed), Verlag chemie, Weinheim, 6a, pp 98–125
Larroche C & Gros JB, 1997, Special transformation processes using fungal spores and immobilized cells, Advanced in Biochemical Engineering and Biotechnology, 55, 179–220
Larroche C, Besson I & Gros JB, 1999, High pyrazine production by Bacillus subtilis in solid substrate fermentation on ground soybeans, Process Biochemistry, 34, 667–674
Larroche C, Creuly C & Gros JB, 1992, 2-heptanone production by spores of Penicillium roquefortii in a water-organic solvent two-phase system, Biocatalysis, 5, 163–173
Lozano P, De Diego T, Guegan JP, Vaultier M & Iborra JL, 2001, Stabilization of α-chymotrypsin by ionic liquids in transesterification reactions, Biotechnology and Bioengeneering, 75, 563–569
Mahato SB & Garai S, 1997, Advances in microbial steroid biotransformation, Steroids, 62, 332–345
Marrs B, Delagrave S & Murphy D, 1999, Novel approaches for discovering industrial enzymes, Current Opinion in Microbiology, 2, 241–245
Martin & Skerman, 1972, World directory of culture collections of microorganisms, Wiley-lnterscience, new-York
Masschelein CA, Ryder DS & Simon JP, 1994, Immobilized cell technology in beer production, Critical Reviews in Biotechnology, 14, 155–177.
McBeath G & Hilvert D, 1994, Monitoring catalytic activity by immunoassay: implications for screening, Journal of the American Chemical Society, 116, 6101–6106
Michaelis L & Menten ML, 1913, The kinetics of invertin action, Biochemistry Z., 49, 333–369
Mihara Y, Utagawa T, Yamada H & Asano Y, 2000, Phosphorylation of nucleosides by the mutated acid phosphatase from Morganella morganii, Applied and Environmental Microbiology, 66, 2811–2816
Mikami Y, 1988, Microbial conversion of terpenoïds, Biotechnological Genetic and Engineering Reviews, 6, 271–320
Murray HC & Peterson DH, 1952, Oxygenation of steroids by mucorales fungi, U.S. Patent 2602769 (Upjohn Co., Kalamazoo, Michigan, USA)
Norton S & Vuillemard JC, 1994, Food bioconversions and metabolite production using immobilized cell technology, Critical Review of Biotechnology, 14, 193–224
Olsen M, Iverson B & Georgiou G, 2000, High-throughput screening of enzyme libraries, Current Opinion in Biotechnology, 11, 331–337
Overhage J, Steinbuchel A & Priefert H, 2003, Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli, Applied and Environmental Microbiology, 69, 6569–6576
Patel RN, 2001, Enzymatic synthesis of chiral intermediates for Omapatrilat, an antihypertensive drug, Biomolecular Engineering, 17, 167–182
Ratledge C, (ed), 1994, Biochemistry of microbial degradation, Kluwer Academic Publishers, Dordrecht, The Netherlands
Reetz MT, Kühling KM, Wilensek S, Husmann H, Häusig UH & Hermes M, 2000, A Ge-based method for high-throughput screening of enantioselective catalysts, Catalysis Today, 67, 389–396
Richard J & Benoit JP, 2000, Microencapsulation, In- Techniques de l’Ingénieur - Traité Génie des Procédés, J2-I210, 1-20
Rosevear A, 1984, Immobilised biocatalyst - a critical review, Journal of Chemical and Technical Biotechnology, 348, 127–150
Sangiliyandi G & Gunasekaran P, 1998, A simple method for purification of thermostable levansucrase of Zymomonas mobilis from a recombinant Escherichia coli. Journal of Microbiological Methods, 33, 153–156
Sangiliyandi G & Gunasekaran P, 2000, A simple method for the purification of over-expressed extracellular sucrase of Zymomonas mobilis from a recombinant Escherichia coli, Biotechnology Letters, 22, 1059–1062
Schrader J & Berger RG, 2001, Biotechnological production of terpenoid flavor and fragrance compounds, In- Biotechnology, vol 10, H-J Rehm (ed), VCH-Wiley, Weinheim, pp 374–415
Seitz EW, 1994, Fermentation production of pyrazines and terpenoids for flavours and fragrances, In- Bioprocess production of flavour, fragrance, and color ingredients, A Gabelman (ed), John Wiley & sons New York, pp 95–134
Shukla OP & Battacharyya PK, 1968a, Microbial transformations of terpenes: Part X- pathways of degradation of α- and β-pinenes in a soil pseudomonad (PL- strain), Indian Journal of Biochemistry, 5, 92–101
Shukla OP, Moholay MN & Battacharyya PK, 1968b, Microbial transformations of terpenes: Part IX-Fermentation of α- and β-pinenes by a soil pseudomonad (PL-strain), Indian Journal of Biochemistry 5, 79–91
Sikkema J, de Boot JAM & Poolman B, 1995, Membrane toxicity of cyclic hydrocarbons, Microbiological Reviews, 59, 201–222
Smidsrød O & Skjåk-Braek G, 1990, Alginate as immobilization matrix for cells, Trends in Biotechnology, 8, 71–78
Souza de Pereira R, 1998, The use of baker’s yeast in the generation of asymmetric centers to produce chiral drugs and other compounds, Critical Reviews in Biotechnology, 18, 25–64
Stahl S, Greasham R & Chartrain M, 2000, Implementation of a rapid screening procedure for biotransformation activities, Journal of Biosciences and Bioengineering, 89, 367–371
Straathof AJJ, Panke S & Schmid A, 2002, The production of fine chemicals by biotransformations, Current Opinions in Biotechnology, 13, 548–556
Tan Q & Day DF, 1998, Bioconversion of limonene to α-terpineol by immobilized Pennicillium digitatum, Applied Microbiology and Biotechnology, 49, 96–101
Tawfik DS, Green BS, Chap R, Sela M & Eshhar Z, 1993, CatELISA: a facile general route to catalytic antibodies. Proceedings of the National Academy of Sciences, USA, 90: 373–377
Taylor SJC, Brown RC, Keene PA & Taylor IN, 1999, Novel screening methods—the key to cloning commercially successful biocatalysts, Bioorganic & Medicinal Chemistry., 7, 2163–2168
Trudgill PW, 1986, Terpenoid metabolism by Pseudomonas, In-The bacteria, Vol.X: The biology of Pseudomonas, JR Sokatch (ed), Academic Press
Trudgill PW, 1994, Microbial metabolism and transformation of selected monoterpenes, In- Biochemistry of microbial degradation, C Ratledge (ed), Kluwer Academic Publishers, Dordrecht, pp 33–61
Tudrozen NJ, Kelly DP & Millis NF, 1977, α-pinene metabolism by Pseudomonas putida, Biochemical Journal, 168, 312–318
van der Werf MJ, Hartrnans S & van den Tweel WJJ, 1995, Permeabilization and lysis of Pseudomonas pseudoalcaligenes cells by Triton X-100 for efficient production of D-malate, Applied Microbiology and Biotechnology, 43, 590–594
van der Werf MJ, de Boot JAM & Leak DJ, 1997, Opportunities in microbial biotransformation of monoterpenes, Advanced in Biochemistry Engineering and Biotechnology, 55, 147–177
van der Werf MJ, Swarts HJ & de Boot JA, 1999, Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene, Applied and Environmental Microbiology, 65, 2092–102
van der Werf MJ, Keijzer PM & van der Schaft PH, 2001, Xanthobacter sp. C20 contains a novel bioconversion pathway for limonene, Journal of Biotechnology, 84, 133–143
van Dyk MS, van Rensburg E & Moleleki N, 1998, Hydroxylation of ( +) limonene, (-) α-pinene and (-) β-pinene by Hormonema sp., Biotechnology Letters, 20, 431–436
Vanderbergh PA, 1989, Bacterial method and compositions for linalool degradation, U.S. Patent, 4, 800, 158
Vasic-Racki D, 2000, History of industrial biotransformations- dreams and realities, In- Industrial Biotransformations, A Liese, K Seelbach, C Wandrey (eds), VCH-Wiley, Weinheim, pp 3–27
Wackett LP & Hershberger CD, 2001a, General concepts in biodegradation and biocatalysis, In- Biocatalysis and Biodegradations, LP Wackett & CD Hershberger (eds), ASM Press, Washington, pp 1–5
Wackett LP & Hershberger CD, 2001b, A history of concepts in biodegradation and microbial catalysis, In- Biocatalysis and Biodegradations,. LP Wackett & CD Hershberger (eds), ASM Press, Washington, pp 7–23
Wahler D & Reymond JL, 2001a, High-throughput screening for biocatalysts, Current Opinion in Biotechnology, 12, 535–44
Wahler D & Reymond JL, 2001b, Novel methods for biocatalyst screening, Current Opinion in Chemistry and Biology, 5, 152–158
Willaers RG & Baron GV, 1996, Gel entrapment and micro-encapsulation: methods, application and engineering principles, Reviews in Chemical Engineering, 12, 1–204
Wise ML & Croteau RB, 1999, Monoterpene biosynthesis, In- Comprehensive natural product chemistry: isoprenoids, Cane (ed), Elsevier, Oxford, pp 9715
Yoo SK & Day DF, 2002, Bacterial metabolism of α- and β-pinene and related monoterpenes by Pseudomonas sp. Strain PIN, Process Biochemistry, 37, 739–745
Zorn H, Neuser F & Berger RG, 2004, Degradation of alpha-pinene oxide and [2 H(7)]- 2,5,6-trimethyl-hept(2E)-enoic acid by Pseudomonas fluorescens NCIMB 11761, Journal of Biotechnology, 107, 255–263
Editor information
Rights and permissions
Copyright information
© 2006 Springer Science+Business Media, Inc. and Asiatech Publishers, Inc.
About this chapter
Cite this chapter
Fontanille, P., Gros, JB., Larroche, C. (2006). Biotransformations with Crude Enzymes and Whole Cells. In: Pandey, A., Webb, C., Soccol, C.R., Larroche, C. (eds) Enzyme Technology. Springer, New York, NY. https://doi.org/10.1007/978-0-387-35141-4_7
Download citation
DOI: https://doi.org/10.1007/978-0-387-35141-4_7
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4419-2124-6
Online ISBN: 978-0-387-35141-4
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)