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).
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References
Zaks, A. and Klibanov, A.M. (1984) Enzymatic catalysis in organic media at 100°C. Science 224, 1249–1251.
Klibanov, A.M. (1986) Enzymes that work in organic solvents. Chemtech, 354–359.
Klibanov, A.M. (1990) Asymmetric transformations catalyzed by enzymes in organic solvents. Acc. Chem. Res., 23, 114–120.
Wong, C.H. and Whitesides, G.M. (1994) Enzymes in Synthetic Organic Chemistry, Pergamon, Elsevier, Amsterdam.
Faber, K. (1992) Biotransformations in Organic Chemistry, Springer-Verlag, Berlin.
Davies, H.G., Green, R.H., Kelly, D.R. and Roberts, S.M. (1989) Biotransformations in Preparative Organic Chemistry, Academic Press, New York.
Abramowicz, D.A. (ed.) (1990) Biocatalysis, Van Nostrand Reinhold, New York.
Halgas, J. (1992) Biocatalysts in Organic Synthesis, Elsevier, Amsterdam.
Poppe, L. and Novak, L. (1992) Selective Biocatalysis, Verlag Chemie, Weinheim, Germany.
Holland, H.L. (1992) Organic Synthesis with Oxidative Enzymes, Verlag Chemie, Weinheim, Germany.
Faber, K. and Franssen, M.C.R. (1993) Prospects for the increased application of biocatalysts in organic transformations, Tibtech, 11, 461–470.
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.
Tramper, J., Vermue, M.H., Beeftink, H.H. and von Stockar, U. (eds) (1992) Biocatalysis in Non-Conventional Media, Elsevier, Amsterdam.
Laane, C, Tramper, J. and Lilly, M.D. (eds) (1987) Biocatalysis in Organic Media, Elsevier, Amsterdam.
Gerhartz, W. (ed.) (1991) Enzymes in Industry. Production and Application, Verlag Chemie, Weinheim, Germany,
Dordick, J.S. (ed.) (1991) Biocatalysts for Industry, Plenum Press, New York.
Falch, E.A. (1991) Industrial enzymes—developments in production and application, Biotech. Advan., 9, 643–658.
Arbige, M.V and Pitcher, W.H. (1989). Industrial enzymology: a look towards the future, Trends Biotech., 7, 330–335.
Björkling, F., Godtfredsen, S.E. and Kirk, O. (1991) The future impact of industrial lipases, Trends Biotech., 9, 360–363.
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.
Sheldon, R.A. (1994) Consider the environmental quotient, Chemtech, 38–47.
Sheldon, R.A. (1992) Organic synthesis—past, present and future, Chem. Ind., London, 903–906.
Sheldon, R.A. (1993) Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York.
Collins, A.N., Sheldrake, G.N. and Crosby, J. (eds) (1992) Chirality in Industry, Wiley, New York.
Cheetham, P.S.J. (1993) The use of biotransformations for the production of flavours and fragrances, Tibtech, 11, 478–488.
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.
Oyama, K. and Kihara, K. (1984) A new horizon for enzyme technology, Chemtech, 100–104.
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.
Samdani, G., Moore, S. and Ondrey, G. (1993) Enzymes move from nature to the plant, Chem. Eng., December, 35–39.
Estell, D.A. (1993) Engineering enzymes for improved performance in industrial applications. J. Biotechnol., 28, 25–30.
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.
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.
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.
Arnold, F.H. (1990) Engineering enzymes for non-aqueous solvents. Tibtech, 8, 244–249.
Hilvert, D. (1991) Extending the chemistry of enzymes and abzymes, Tibtech, 9, 11–17.
St. Clair, NX. and Navia, M.A. (1992) Cross-linked enzyme crystals as robust biocatalysts. J. Amer. Chem. Soc., 114, 7314–7316.
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.
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.
Nakamura, K., Kondo, S., Kawai, Y. and Ohno, A. (1991) Reduction by baker’s yeast in benzene, Tetrahedron Lett., 32, 7075–7078.
Macrae, A.R. (1983) Lipase-catalyzed interesterification of oils and fats, J. Amer. Oil. Chem. Soc., 60, 291–294.
Macrae, A.R. and Hammond, R.C. (1985) Present and future applications of lipases, Biotech. Genet. Eng. Rev., 3, 193–217.
Coleman, M.H. and Macrae, A.R. (1980) Fat process and composition. UK Patent 1577993, to Unilever.
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.
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,
King, D.M. and Padley, F.B. (1990) Milk fat substitutes, European Patent 0209327, to Unilever.
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.
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.
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.
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.
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.
De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1995) submitted foir publication.
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.
Macrae, A., Roehl, E.L. and Brand, H.M. (1990) Bioesters in cosmetics, Drug Cosmet. Ind., 147, 36–39.
Koch, M., Beck, R. and Röper, H. (1993) Starch-derived products for detergents, Starch/Stärke, 45, 2–7, and references cited therein.
Riva, S. and Secundo, F. (1990) Selective enzymatic acylations and deacylations of carbohydrates and related compounds, Chimicaoggi, June, 9–16.
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.
Therisod, M. and Klibanov, A.M. (1986) Facile enzymatic preparation of monoacylated sugars in pyridine, J. Amer. Chem. Soc., 108, 5638–5640.
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.
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.
Adelhorst, K., Björkling, F., Godtfredsen, S.E. and Kirk, O. (1990) Enzyme-catalyzed preparation of 6-O-acylglucopyranosides, Synthesis, 112–115.
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.
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.
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.
Njar, V.C.O. and Caspi, E. (1987) Enzymatic transesterification of steroid esters in organic solvents, Tetrahedron Lett., 28, 6549–6552.
Teranishi, R., Takeoka, G.R. and Güntert, M. (eds) (1992) Flavor Precursors, ACS Symposium Series, vol. 490, American Chemical Society, Washington, DC.
Langrand, G., Rondot, N., Triantaphylides, C. and Baratti, J. (1990) Short–chain flavor esters synthesis by microbial lipases. Biotechnol. Lett., 12, 581–586.
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.
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.
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.
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.
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.
Engel, K-H. (1992) Lipase-catalyzed enantioselective acidolysis of chiral 2-methylalkanoates, J. Amer. Oil Chem. Soc., 69, 146–150.
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.
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.
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.
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.
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.
Makita, A., Nihira, I. and Yamada, Y. (1987) Lipase catalysed synthesis of macrocylic lactones in organic solvents, Tetrahedron Lett., 28, 805–808.
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.
Stinton, S. (1994) Chiral drugs, Chem. Eng. News, September 19, 38–72.
Ramos Tombo, G.M. and Bellus, D. (1991) Chiralität und Pflanzenschutz, Angew. Chem., 103, 1219–1241.
Ariens, E.J., van Rensen, J.J.S. and Welling, W. (eds) (1988) Stereoselectivity of Pesticides, Elsevier, Amsterdam.
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.
Margolin, A.L. (1993) Enzymes in the synthesis of chiral drugs, Enzym. Microb. Technol., 15, 266–280.
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.
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.
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.
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.
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.
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.
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.
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.
Bevinakatti, H.S. and Banerji, A.A. (1991) Practical chemoenzymatic synthesis of both enantiomers of propranolol, J. Org. Chem., 56, 5372–5375.
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.
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.
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.
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.
Battistel, E., Bianchi, D., Cesti, P. and Pina, C. (1991) Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor, Biotechnol. Bioeng., 38, 659–664.
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.
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.
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.
Klibanov, A.M. and Kirchner, G. (1986) Enzymatic production of 2-halopropionic acids, US Patent 4,601,987, to Massachusetts Institute of Technology.
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.
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.
Sugai, T. and Ohta, H. (1991) A simple preparation of (R)-2-hydroxy-4-phenylbutanoic acid, Agric. Biol. Chem., 55, 293–294.
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.
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.
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.
De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1994) Lipase-catalyzed transformations with unnatural acyl acceptors, Catalysis Today, 22, 563–590.
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.
De Zoete, M.C., van Rantwijk, F. and Sheldon, R.A. (1994) Enzymatic ammoniolysis, International Patent Application PCT/EP94/03038.
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.
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.
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.
Becker, W. and Pfeil, E. (1966) The flavine enzyme, d-hydroxynitrilase, Biochemistry, 346, 301–321.
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.
Effenberger, F., Ziegler, T. and Förster, S. (1987) Enzyme catalyzed cyanohydrin synthesis in organic solvents, Angew. Chem. Int. Ed. Engl., 26, 458–459.
Kula, M.R., Stürtz, I.M., Wandrey, C. and Krag, U. (1991) European Patent 446826, to Forschungszentrum Julich.
Andruski, S.W. and Goldberg, B. (1991) Process for preparing optically active cyanohydrins with enzymes, US Pat. 5177242, to FMC Corp.
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.
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.
Kiljunen, E. and Kanerva, L.T. (1994) Sorghum bicolor shoots in the synthesis of (S)-mandelonitrile, Tetrahedron Assymmetry, 5, 311–314.
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.
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.
Dordick, J.S. (1992) Enzymatic and chemoenzymatic approaches to polymer synthesis, Tibtech, 10 (August) 187–293, and references cited therein.
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.
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.
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.
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.
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.
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.
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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
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