Skip to main content

Large-scale enzymatic conversions in non-aqueous media

  • Chapter
Enzymatic Reactions in Organic Media

Abstract

During the last decade the organic chemist’s and the chemical industry’s perception of enzymes has changed dramatically. The traditional view was based on the conventional wisdom that the use of enzymes is restricted to aqueous media and temperatures close to ambient. Moreover, enzymes were perceived as being very expensive, fragile catalysts that present substantial problems in handling and downstream processing, i.e. hardly the sort of reagent one would consider for use in industrial organic synthesis. Conventional wisdom also held that enzymes are very substrate- and reaction-specific (the one enzyme—one reaction—one substrate paradigm).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Zaks, A. and Klibanov, A.M. (1984) Enzymatic catalysis in organic media at 100°C. Science 224, 1249–1251.

    Article  CAS  Google Scholar 

  2. Klibanov, A.M. (1986) Enzymes that work in organic solvents. Chemtech, 354–359.

    Google Scholar 

  3. Klibanov, A.M. (1990) Asymmetric transformations catalyzed by enzymes in organic solvents. Acc. Chem. Res., 23, 114–120.

    Article  CAS  Google Scholar 

  4. Wong, C.H. and Whitesides, G.M. (1994) Enzymes in Synthetic Organic Chemistry, Pergamon, Elsevier, Amsterdam.

    Google Scholar 

  5. Faber, K. (1992) Biotransformations in Organic Chemistry, Springer-Verlag, Berlin.

    Book  Google Scholar 

  6. Davies, H.G., Green, R.H., Kelly, D.R. and Roberts, S.M. (1989) Biotransformations in Preparative Organic Chemistry, Academic Press, New York.

    Google Scholar 

  7. Abramowicz, D.A. (ed.) (1990) Biocatalysis, Van Nostrand Reinhold, New York.

    Google Scholar 

  8. Halgas, J. (1992) Biocatalysts in Organic Synthesis, Elsevier, Amsterdam.

    Google Scholar 

  9. Poppe, L. and Novak, L. (1992) Selective Biocatalysis, Verlag Chemie, Weinheim, Germany.

    Google Scholar 

  10. Holland, H.L. (1992) Organic Synthesis with Oxidative Enzymes, Verlag Chemie, Weinheim, Germany.

    Google Scholar 

  11. Faber, K. and Franssen, M.C.R. (1993) Prospects for the increased application of biocatalysts in organic transformations, Tibtech, 11, 461–470.

    Article  CAS  Google Scholar 

  12. Dordick, J.S. (1991) Principles and applications of nonaqueous enzymology. In Applied Biocatalysis, vol. 1 (eds H.W. Blanch and D.S. Clark), Marcel Dekker, New York, pp. 1–51.

    Google Scholar 

  13. Tramper, J., Vermue, M.H., Beeftink, H.H. and von Stockar, U. (eds) (1992) Biocatalysis in Non-Conventional Media, Elsevier, Amsterdam.

    Google Scholar 

  14. Laane, C, Tramper, J. and Lilly, M.D. (eds) (1987) Biocatalysis in Organic Media, Elsevier, Amsterdam.

    Google Scholar 

  15. Gerhartz, W. (ed.) (1991) Enzymes in Industry. Production and Application, Verlag Chemie, Weinheim, Germany,

    Google Scholar 

  16. Dordick, J.S. (ed.) (1991) Biocatalysts for Industry, Plenum Press, New York.

    Google Scholar 

  17. Falch, E.A. (1991) Industrial enzymes—developments in production and application, Biotech. Advan., 9, 643–658.

    Article  CAS  Google Scholar 

  18. Arbige, M.V and Pitcher, W.H. (1989). Industrial enzymology: a look towards the future, Trends Biotech., 7, 330–335.

    Article  CAS  Google Scholar 

  19. Björkling, F., Godtfredsen, S.E. and Kirk, O. (1991) The future impact of industrial lipases, Trends Biotech., 9, 360–363.

    Article  Google Scholar 

  20. Vulfson, E.N. (1994) Industrial applications of lipases. In Lipases, their Structure, Biochemistry and Application (eds P. Woolley and S.B. Petersen), Cambridge University Press, Cambridge.

    Google Scholar 

  21. Sheldon, R.A. (1994) Consider the environmental quotient, Chemtech, 38–47.

    Google Scholar 

  22. Sheldon, R.A. (1992) Organic synthesis—past, present and future, Chem. Ind., London, 903–906.

    Google Scholar 

  23. Sheldon, R.A. (1993) Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York.

    Google Scholar 

  24. Collins, A.N., Sheldrake, G.N. and Crosby, J. (eds) (1992) Chirality in Industry, Wiley, New York.

    Google Scholar 

  25. Cheetham, P.S.J. (1993) The use of biotransformations for the production of flavours and fragrances, Tibtech, 11, 478–488.

    Article  CAS  Google Scholar 

  26. Randolph, T.W., Blanch, H.W. and Clark, D.S. (1991) Biocatalysis in supercritical fluids. In Biocatalysts for Industry (ed. J.S. Dordick) Plenum Press, New York.

    Google Scholar 

  27. Oyama, K. and Kihara, K. (1984) A new horizon for enzyme technology, Chemtech, 100–104.

    Google Scholar 

  28. Oyama, K. (1992) The industrial production of aspartame. In Chirality in Industry (eds A.N. Collins, G.N. Sheldrake and J. Crosby) Wiley, New York, pp. 237–247.

    Google Scholar 

  29. Samdani, G., Moore, S. and Ondrey, G. (1993) Enzymes move from nature to the plant, Chem. Eng., December, 35–39.

    Google Scholar 

  30. Estell, D.A. (1993) Engineering enzymes for improved performance in industrial applications. J. Biotechnol., 28, 25–30.

    Article  CAS  Google Scholar 

  31. Estell, D.A., Gaycar, T.P. and Wells, J.A. (1985) Engineering an enzyme by site-directed mutagenesis to be resistant to chemical oxidation. J. Biol. Chem., 260, 6518–6521.

    CAS  Google Scholar 

  32. Bott, R., Shield, J.W. and Poulose, A J. (1994) Protein engineering of lipases. In Lipases, Their Structure, Biochemistry and Application (eds P. Woolley and S.B. Petersen) Cambridge University Press, Cambridge.

    Google Scholar 

  33. Hwang, J.Y. and Arnold, EH. (1991) Enzyme design for nonaqueous solvents. In Applied Biocatalysis, vol. 1 (eds H.W. Blanch and D.S. Clark), Marcel Dekker, New York, pp. 53–86.

    Google Scholar 

  34. Arnold, F.H. (1990) Engineering enzymes for non-aqueous solvents. Tibtech, 8, 244–249.

    Article  CAS  Google Scholar 

  35. Hilvert, D. (1991) Extending the chemistry of enzymes and abzymes, Tibtech, 9, 11–17.

    Article  CAS  Google Scholar 

  36. St. Clair, NX. and Navia, M.A. (1992) Cross-linked enzyme crystals as robust biocatalysts. J. Amer. Chem. Soc., 114, 7314–7316.

    Article  CAS  Google Scholar 

  37. Sobolov, S.B., Bartoszko-Malik, A., Oeschger, T.R. and Montelbano, M.M. (1994) Cross-linked enzyme crystals of fructose diphosphate aldolase: development as a biocatalyst for synthesis, Tetrahedron Lett., 35, 7751–7754.

    CAS  Google Scholar 

  38. Chibata, I., Tosa, T. and Shibatani, T. (1992) The industrial production of optically active compounds by immobilized biocatalysts. In Chirality in Industry (eds A.N. Collins, G.N. Sheldrake and J. Crosby), Wiley, New York, pp. 351–370.

    Google Scholar 

  39. Nakamura, K., Kondo, S., Kawai, Y. and Ohno, A. (1991) Reduction by baker’s yeast in benzene, Tetrahedron Lett., 32, 7075–7078.

    Article  CAS  Google Scholar 

  40. Macrae, A.R. (1983) Lipase-catalyzed interesterification of oils and fats, J. Amer. Oil. Chem. Soc., 60, 291–294.

    Article  CAS  Google Scholar 

  41. Macrae, A.R. and Hammond, R.C. (1985) Present and future applications of lipases, Biotech. Genet. Eng. Rev., 3, 193–217.

    CAS  Google Scholar 

  42. Coleman, M.H. and Macrae, A.R. (1980) Fat process and composition. UK Patent 1577993, to Unilever.

    Google Scholar 

  43. Matsuo, T., Sawamura, N., Hashimoto, Y. and Hashida, W. (1981) Method for enzymatic transesterification of lipid and enzyme used therein. European Patent 0035883, to Fuji Oil.

    Google Scholar 

  44. Quinlan, P. and Moore, S. (1993) Modification of triglycerides by lipases: process technology and its application to the production of nutritionally improved fats, Inform, 4, 580–585,

    Google Scholar 

  45. King, D.M. and Padley, F.B. (1990) Milk fat substitutes, European Patent 0209327, to Unilever.

    Google Scholar 

  46. Jandacek, R., Whiteside, J.A., Holcombe, B.N., Volpenheim, R.A. and Taulbee, J.D. (1987) The rapid hydrolysis and efficient absorption of triglycerides with octanoic acid in the 1 and 3 positions and long-chain fatty acid in the 2 position, Amer. J. Clin. Nutr., 45, 940–945.

    CAS  Google Scholar 

  47. Mukherjee, K.D. and Kiewitt, I. (1991) Enrichment of γ-linoleic acid from fungal oil by lipase-catalysed reactions. Appl. Microbiol. Biotechnol., 35, 579–584.

    Article  CAS  Google Scholar 

  48. Zaks, A. and Bross, A.T. (1990) Production of glycerides rich in omega-3 fatty acids by lipase-catalysed transesterification and recrystallization, International Patent WO 90/13656, to Enzytech Inc.

    Google Scholar 

  49. De Zoete, M.C., Kock-van Dalen, A.C., van Rantwijk, F. and Sheldon, R.A. (1993) Ester ammoniolysis: a new enzymatic reaction, J. Chem. Soc., Chem. Commun., 1831–1832.

    Google Scholar 

  50. De Zoete, M.C., Kock-van Dalen, A.C., van Rantwijk, F. and Sheldon, R.A. (1994) A new enzymatic reaction: enzyme catalyzed ammoniolysis of carboxylic esters, Biocatalysis, 10, 307–316.

    Article  Google Scholar 

  51. De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1995) submitted foir publication.

    Google Scholar 

  52. Hills, G.A., Macrae, A.R. and Poulina, R.R. (1990) Esters preparation from acids and alcohols with lipase catalyst and azeotropic distillation of alcohol and obtained water, European Patent 0383405, to Unichema B.V.

    Google Scholar 

  53. Macrae, A., Roehl, E.L. and Brand, H.M. (1990) Bioesters in cosmetics, Drug Cosmet. Ind., 147, 36–39.

    Google Scholar 

  54. Koch, M., Beck, R. and Röper, H. (1993) Starch-derived products for detergents, Starch/Stärke, 45, 2–7, and references cited therein.

    Article  Google Scholar 

  55. Riva, S. and Secundo, F. (1990) Selective enzymatic acylations and deacylations of carbohydrates and related compounds, Chimicaoggi, June, 9–16.

    Google Scholar 

  56. De Goede, A.T.J.W, Woudenberg-van Oosterom, M. and Van Rantwijk, F. (1994) Selective lipase-catalyzed esterification of carbohydrates, Carbohydrates in Europe, May, 18–20.

    Google Scholar 

  57. Therisod, M. and Klibanov, A.M. (1986) Facile enzymatic preparation of monoacylated sugars in pyridine, J. Amer. Chem. Soc., 108, 5638–5640.

    Article  CAS  Google Scholar 

  58. Riva, S., Chopineau, J., Kieboom, A.P.G. and Klibonov, A.M. (1988) Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethyl-formamide, J. Amer. Chem. Soc., 110, 584–589.

    Article  CAS  Google Scholar 

  59. Björkling, F.M., Godtfredsen, S.E. and Kirk, O. (1989) A highly selective enzyme catalyzed esterification of simple glucosides, J. Chem.. Soc, Chem. Commun., 924–925.

    Google Scholar 

  60. Adelhorst, K., Björkling, F., Godtfredsen, S.E. and Kirk, O. (1990) Enzyme-catalyzed preparation of 6-O-acylglucopyranosides, Synthesis, 112–115.

    Google Scholar 

  61. De Goede, A.T.J.W., van Oosterom, M., van Deurzen, M.P.J., Sheldon, R.A., van Bekkum, H. and van Rantwijk, F. (1994) Selective lipase-catalyzed esterification of alkylglycosides, Biocatalysis, 9, 145–155.

    Article  Google Scholar 

  62. Sheldon, R.A., van Rantwijk, F. and Woudenberg-van Oosterom, M. (1995) Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica, Biotechnol. Bioeng., accepted for publication.

    Google Scholar 

  63. Riva, S. (1991) Enzymatic modification of steroids. In Applied Biocatalysis, vol. 1 (eds H.W. Blanch and D.C. Clark) Marcel Dekker, New York, pp. 179–220.

    Google Scholar 

  64. Njar, V.C.O. and Caspi, E. (1987) Enzymatic transesterification of steroid esters in organic solvents, Tetrahedron Lett., 28, 6549–6552.

    Article  CAS  Google Scholar 

  65. Teranishi, R., Takeoka, G.R. and Güntert, M. (eds) (1992) Flavor Precursors, ACS Symposium Series, vol. 490, American Chemical Society, Washington, DC.

    Google Scholar 

  66. Langrand, G., Rondot, N., Triantaphylides, C. and Baratti, J. (1990) Short–chain flavor esters synthesis by microbial lipases. Biotechnol. Lett., 12, 581–586.

    Article  CAS  Google Scholar 

  67. Chulaksananukul, W., Condoret, J.S. and Combes, D. (1992) Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane, Enzym. Microb. Technol., 14, 293–298.

    Article  Google Scholar 

  68. Fonteyn, F.M., Blecker, C, Lognoy, G., Marlier, M. and Severin, M. (1994) Optimization of lipase-catalyzed synthesis of citronellol acetate in solvent-free medium, Biotechnol, Lett., 16, 693–696.

    Article  CAS  Google Scholar 

  69. Mosandi, A., Heusinger, G. and Gessner, M. (1986) Analytical and sensory differentiation of l-octen-3-ol enantiomers, J. Agric. Food Chem., 34, 119–122.

    Article  Google Scholar 

  70. Engel, K-H. (1992) Lipases: useful biocatalysts for enantioselective reactions of chiral flavor compounds. In Flavor Precursors (R. Teranishi, G.R. Takeoka and M. Güntert, eds) American Chemical Society, Washington, DC, pp. 20–31.

    Google Scholar 

  71. Lutz, D., Huffer, M., Gerlach, D. and Schreier, R (1992) Carboxylester–lipase mediated reactions: a versatile route to chiral molecules. In Flavor Precursors (R. Teranishi, G.R. Takeoka and M. Güntert, eds) American Chemical Society, Washington, DC, pp. 32–45.

    Chapter  Google Scholar 

  72. Engel, K-H. (1992) Lipase-catalyzed enantioselective acidolysis of chiral 2-methylalkanoates, J. Amer. Oil Chem. Soc., 69, 146–150.

    Article  CAS  Google Scholar 

  73. Uemasu, I. and Hinze, W.L. (1994) Enantioselective esterification of 2-methylbutyric acid catalyzed via lipase immobilized in microemulsion-based organogels, Chirality, 6, 649–653.

    Article  CAS  Google Scholar 

  74. Engel, K-H., Heidlas, J., Albrecht, W. and Tressl, R. (1989). Biosynthesis of achiral flavor and aroma compounds in plants and microorganisms. In Flavor Chemistry, Trends and Developments (eds R. Teranishi, R.G. Buttery and F. Shahidi) ACS Symposium Series, vol. 388, American Chemical Society, Washington, DC, pp. 8–22.

    Chapter  Google Scholar 

  75. Engel, K-H., Bohnen, M. and Dobe, M. (1991) Lipase-catalyzed reactions of chiral hydroxyl-acid esters: competition of esterification and transesterification, Enzym. Microb. Technol., 13, 655–660.

    Article  CAS  Google Scholar 

  76. Albrecht, W., Heidlas, J., Schwarz, M. and Tressl, R. (1992) Biosynthesis and biotechnological production of aliphatic γ- and δ-lactones. In Flavor Precursors (R. Teranishi, G.R. Takeoka and M. Güntert, eds) American Chemical Society, Washington, DC, pp. 46–58.

    Chapter  Google Scholar 

  77. Gutman, A.L., Zuobi, K. and Boltansky, A. (1987) Enzymatic lactonisation of γ-hydroxyesters in organic solvents. Synthesis of optically pure γ-methylbutyrolactones and γ-phenylbutyro-lactone, Tetrahedron Lett., 28, 3861–3864.

    Article  CAS  Google Scholar 

  78. Makita, A., Nihira, I. and Yamada, Y. (1987) Lipase catalysed synthesis of macrocylic lactones in organic solvents, Tetrahedron Lett., 28, 805–808.

    Article  CAS  Google Scholar 

  79. Yamada, H., Ohsawa, S., Sugai, T., Ohta, H. and Yashikawa, S. (1989) Lipase-catalyzed highly enantioselective macrolactonization of hydroxyacid esters in an organic solvent, Chem. Lett., 1775–1776.

    Google Scholar 

  80. Stinton, S. (1994) Chiral drugs, Chem. Eng. News, September 19, 38–72.

    Google Scholar 

  81. Ramos Tombo, G.M. and Bellus, D. (1991) Chiralität und Pflanzenschutz, Angew. Chem., 103, 1219–1241.

    Article  CAS  Google Scholar 

  82. Ariens, E.J., van Rensen, J.J.S. and Welling, W. (eds) (1988) Stereoselectivity of Pesticides, Elsevier, Amsterdam.

    Google Scholar 

  83. Sih, C.J., Gu, Q.-M., Fülling, G., Wu, S.-H. and Reddy, D.R. (1988) The use of microbial enzymes for the synthesis of optically active pharmaceuticals, Dev. Ind. Microb., 29, 221–229.

    CAS  Google Scholar 

  84. Margolin, A.L. (1993) Enzymes in the synthesis of chiral drugs, Enzym. Microb. Technol., 15, 266–280.

    Article  CAS  Google Scholar 

  85. Ader, U., Andersch, P., Berger, M., Goergens, U., Seemayer, R. and Schneider, M. (1992) Hydrolases in organic synthesis: preparation of enantiomerically pure compounds, Pure Appl. Chem., 64, 1165–1170.

    Article  CAS  Google Scholar 

  86. Bianchi, D., Cesti, P., Golini, P., Spezia, S., Garavaglia, C. and Mirenna, L. (1992) Enzymatic preparation of optically active fungicide intermediates in aqueous and organic media, Pure Appl. Chem., 64, 1073–1078.

    Article  CAS  Google Scholar 

  87. Kloosterman, M., Elferink, V.H.M., van Iersel, J., Roskam, J.H., Meyer, E.M., Hulshof, L.A. and Sheldon, R.A. (1988) Lipases in the preparation of beta-blockers, Tibtech., 6, 251–256.

    Article  CAS  Google Scholar 

  88. Ladner, W.E. and Whitesides, G.M. (1984) Lipase-catalyzed hydrolysis as a route to esters of chiral epoxy alcohols, J. Amer. Chem. Soc., 106, 7250–7251.

    Article  CAS  Google Scholar 

  89. Chen, C.S., Liu, Y.C. and Marsella, M. (1990) A convenient chemoenzymatic synthesis of (R)- and (S)-chloromethyloxirane, J. Chem.. Soc., Perkin Trans. I, 2559–2561.

    Google Scholar 

  90. Ader, U. and Schneider, M. (1992) Enzyme assisted preparation of enantiomerically pure beta-adrenergic blockers I. A facile screening method for suitable biocatalysts, Tetrahedron Assymmetry, 3, 201–204.

    Article  CAS  Google Scholar 

  91. Ader, U. and Schneider, M. (1992) Enzyme assisted preparation of enantiomerically pure beta-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversions, Tetrahedron Asymmetry, 3, 205–208.

    Article  CAS  Google Scholar 

  92. Ader, U. and Schneider, M. (1992) Enzyme assisted preparation of enantiomerically pure beta adrenergic blockers III. Optically active chlorohydrin derivatives and their conversion, Tetrahedron Asymmetry, 3, 531–524.

    Google Scholar 

  93. Bevinakatti, H.S. and Banerji, A.A. (1991) Practical chemoenzymatic synthesis of both enantiomers of propranolol, J. Org. Chem., 56, 5372–5375.

    Article  CAS  Google Scholar 

  94. Hulshof, L.A. and Roskam, J.H. (1989) Phenylglycidate stereoisomers, conversion products thereof with e.g. 2-nitrophenol and preparation of diltiazem, European Patent Application 0343714, to Stamicarbon.

    Google Scholar 

  95. Kanerva, L.T. and Sundholm, O. (1993) Lipase catalysis in the resolution of racemic intermediates of diltiazem synthesis in organic solvents, J. Chem.. Soc. Perkin Trans. I, 1385.

    Google Scholar 

  96. Gou, D.M., Liu, Y.C. and Chen, C.S. (1993) A practical chemoenzymatic synthesis of the taxol C-13 side chain N-benzoyl-(2R,3S)-3-phenylisoserine, J. Org. Chem., 58, 1287–1289.

    Article  CAS  Google Scholar 

  97. Sonawane, H.R., Bellur, N.S., Ahuja, J.R. and Kulkarni, D.G. (1992) Recent developments in the synthesis of optically active α-arylpropionic acids: an important class of non-steroidal anti-inflammatory agents, Tetrahedron Asymmetry, 3, 163–192.

    Article  CAS  Google Scholar 

  98. Battistel, E., Bianchi, D., Cesti, P. and Pina, C. (1991) Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor, Biotechnol. Bioeng., 38, 659–664.

    Article  CAS  Google Scholar 

  99. McConville, F.X., Lopez, J.L. and Wald, S.A. (1990) Enzymatic resolution of ibuprofen in a multiphase membrane reactor. In Biocatalysis (ed. D.A. Abramowicz) Van Nostrand Reinhold, New York, pp. 167–177.

    Google Scholar 

  100. Smeets, J.W.H. and Kieboom, A.P.G. (1992) Enzymatic enantioselective ester hydrolysis by carboxylesterase NP, Recl. Trav. Chim. Pays-Bas, 111, 490–495.

    Article  CAS  Google Scholar 

  101. Giordano, C, Villa, M. and Panossian, S. (1992) Naproxen: industrial asymmetric synthesis. In Chirality in Industry (eds A.N. Collins, G.N. Sheldrake and J. Crosby) Wiley, New York, pp. 303–312.

    Google Scholar 

  102. Klibanov, A.M. and Kirchner, G. (1986) Enzymatic production of 2-halopropionic acids, US Patent 4,601,987, to Massachusetts Institute of Technology.

    Google Scholar 

  103. Cambou, B. and Klibanov, A.M. (1984) Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: asymmetric hydrolysis, esterification and transesterification, Biotechnol. Bioeng., 26, 1449–1454.

    Article  CAS  Google Scholar 

  104. Sheldon, R.A., Zeegers, H.J.M., Houbiers, J.P.M. and Hulshof, L.A. (1991) The synthesis of angtiotensin-converting enzyme (ACE) inhibitors, Chimica oggi (Chemistry Today), May, 35–47.

    Google Scholar 

  105. Sugai, T. and Ohta, H. (1991) A simple preparation of (R)-2-hydroxy-4-phenylbutanoic acid, Agric. Biol. Chem., 55, 293–294.

    Article  CAS  Google Scholar 

  106. Sakimae, A., Hosoi, A., Kobayashi, E., Ohsuga, N., Numazawa, R., Watanabe and Ohnishi, H. (1992) Screening of microorganisms producing d-β-acetylmercaptoisobutyric acid from methyl-dl-β-acetylthioisobutyrate, Biosci. Biotech. Biochem., 56, 1252–1256.

    Article  CAS  Google Scholar 

  107. Hirohara, H., Mitsuda, S., Ando, E. and Komaki, R. (1985) Enzymatic preparation of optically active alcohols related to synthetic pyrethroids insecticides. In Biocatalysts in Organic Synthesis (eds J. Tramper, H.C. van der Plas and P. Linka), Elsevier, Amsterdam, pp. 119–134.

    Google Scholar 

  108. Mitsuda, S. and Nabeshima, S. (1991) Enzymatic optical resolution of a synthetic pyrethroid alcohol. Enantioselective transesterification by lipase in organic solvent, Tecl. Trav. Chim. Pays-Bas, 110, 151–154.

    Article  CAS  Google Scholar 

  109. De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1994) Lipase-catalyzed transformations with unnatural acyl acceptors, Catalysis Today, 22, 563–590.

    Article  Google Scholar 

  110. De Zoete, M.C., Kock-van Dalen, A.C., van Rantwijk, F. and Sheldon, R.A. (1993) Ester ammoniolysis: a new enzymatic reaction, J. Chem.. Soc, Chem. Commun., 1831–1832.

    Google Scholar 

  111. De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1994) Enzymatic ammoniolysis, International Patent Application PCT/EP94/03038.

    Google Scholar 

  112. De Zoete, M.C., Kock-van Dalen, A.C., van Rantwijk, F. and Sheldon, R.A. (1994) A new enzymatic reaction: enzyme-catalyzed ammoniolysis of careboxylic esters, Biocatalysis, 10, 307–316.

    Article  Google Scholar 

  113. De Zoete, M.C., Ouwehand, A.A., van Rantwijk, F. and Sheldon, R.A. (1995) Enzymatic ammoniolysis of amino acid derivatives, Recl. Trav. Chim. Pays-Bas, 114, 171–174.

    Article  Google Scholar 

  114. Kruse, CG. (1992) Chiral Cyanohydrins-their manufacture and utility as chiral building blocks. In Chirality in Industry (eds A.N. Collins, G.N. Sheldrake and J. Crosby), Wiley, New York, pp. 279–299.

    Google Scholar 

  115. Becker, W. and Pfeil, E. (1966) The flavine enzyme, d-hydroxynitrilase, Biochemistry, 346, 301–321.

    CAS  Google Scholar 

  116. Effenberger, F., Hörsch, B., Förster, S. and Ziegler, T. (1990) Enzyme-catalyzed synthesis of (S)-cyanohydrins and subsequent hydrolysis to (S)-a-hydroxycarboxylic acids, Tetrahedron Lett., 31, 1249–1252.

    Article  CAS  Google Scholar 

  117. Effenberger, F., Ziegler, T. and Förster, S. (1987) Enzyme catalyzed cyanohydrin synthesis in organic solvents, Angew. Chem. Int. Ed. Engl., 26, 458–459.

    Article  Google Scholar 

  118. Kula, M.R., Stürtz, I.M., Wandrey, C. and Krag, U. (1991) European Patent 446826, to Forschungszentrum Julich.

    Google Scholar 

  119. Andruski, S.W. and Goldberg, B. (1991) Process for preparing optically active cyanohydrins with enzymes, US Pat. 5177242, to FMC Corp.

    Google Scholar 

  120. Beisswengerm, T., Huthmacher, K. and Klenk, H. (1991) Preparation of d-2,4-dihydroxy-3,3-dimethylbutyronitrile as synthetic intermediate in d-pantolactone synthesis, Ger. Offen. DE 4126580, to Degussa.

    Google Scholar 

  121. Ognyabov, V.I., Datcheva, V.K. and Kyler, K.S. (1991) Preparation of chiral cyanohydrins by an oxynitrilase-mediated transcyanation, J. Amer. Chem. Soc., 113, 6992–6996.

    Article  Google Scholar 

  122. Kiljunen, E. and Kanerva, L.T. (1994) Sorghum bicolor shoots in the synthesis of (S)-mandelonitrile, Tetrahedron Assymmetry, 5, 311–314.

    Article  CAS  Google Scholar 

  123. van Almsick, A., Buddrus, J., Hönicke-Schmidt, Laumen, K. and Schneider, M.P. (1989) Enzymatic preparation of optically active eyanohydrin acetates, J. Chem.. Soc., Chem. Commun., 1391–1393.

    Google Scholar 

  124. Inagaki, M., Hiratake, J., Nishioka, T. and Oda, J. (1991) Lipase-catalyzed kinetic resolution with in-situ racemization: one-pot synthesis of optically active cyanohydrin acetates from aldehydes, J. Amer. Chem. Soc., 113, 9360–9361.

    Article  CAS  Google Scholar 

  125. Dordick, J.S. (1992) Enzymatic and chemoenzymatic approaches to polymer synthesis, Tibtech, 10 (August) 187–293, and references cited therein.

    Google Scholar 

  126. Patil, D.R., Redhwisch, D.G. and Dordick, J.S. (1991) Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous media, Biotechnol, Bioeng., 37, 639–646.

    Article  CAS  Google Scholar 

  127. Dordick, J.S., Marletts, M.A. and Klibanov, A.M. (1987) Polymerization of phenols catalyzed by peroxidase in nonaqueous media, Biotechnol. Bioeng., 13, 964–968.

    Google Scholar 

  128. Popp, J.L., Kirk, T.K. and Dordick, J.S. (1991) Incorporation of p-cresol into lignins via peroxidase-catalyzed copolymerization in nonaqueous media, Enzyme Microb. Technol., 13, 964–968.

    Article  CAS  Google Scholar 

  129. Margolin, A.L., Fitzpatrick, P.A., Dubin, P.L. and Klibanov, A.M. (1991) Chemoenzymatic synthesis of optically active (meth)acrylic polymers, J. Amer. Chem. Soc., 113, 4693–4694.

    Article  CAS  Google Scholar 

  130. Ghogare, A. and Kumar, S. (1990) Novel route to chiral polymers involving biocatalytic transesterification of O-acryloyl oximes, J. Chem.. Soc., Chem. Commun., 134–135.

    Google Scholar 

  131. Martin, B.D., Ampofo, S.A., Linhardt, R.J. and Dordick, J.S. (1992) Biocatalytic synthesis of sugar-containing polyacrylate-based hydrogels, Macromolecules, 25, 7081–7085.

    Article  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Sheldon, R.A. (1996). Large-scale enzymatic conversions in non-aqueous media. In: Koskinen, A.M.P., Klibanov, A.M. (eds) Enzymatic Reactions in Organic Media. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0611-5_10

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-0611-5_10

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4269-7

  • Online ISBN: 978-94-011-0611-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics