Cofactor Regeneration in Biocatalysis in Organic Media

References

• Adlercreutz P. On the importance of the support material for enzymatic synthesis in organic media. Support effects at controlled water activity. Eur. J. Biochem. 1991; 199: 609–614
   PubMedGoogle Scholar
• Adlercreutz P. Activation of enzymes in organic media at low water activity by polyols and saccharides. Biochim. Biophys. Acta 1993; 1163: 144–148
   PubMed Web of Science ®Google Scholar
• Allen P. M., Bowen W. R. Electrochemical regeneration of redox cofactors and mediators - the key to bioelectrosynthesis. Trends Biotechnol. 1985; 3: 145–149
   Web of Science ®Google Scholar
• Bell G., Halling P. J., Moore B. D., Partridge J., Rees D. G. Biocatalyst behaviour in low-water systems. Trends Biotechnol. 1995; 13: 468–473
   Web of Science ®Google Scholar
• Carrea G., Bovara R., Cremonesi P., Lodi R. Enzymatic preparation of 12-ketochenodeoxycholic acid with NADP+ regeneration. Biotechnol. Bioeng. 1984; 26: 560–563
   PubMed Web of Science ®Google Scholar
• Carrea G., Colombi F., Mazzola G., Cremonesi P., Antonini E. Immobilized hydroxysteroid dehydrogenases for the transformation of steroids in water-organic solvent systems. Biotechnol. Bioeng. 1979; 21: 39–48
   PubMed Web of Science ®Google Scholar
• Carrea G., Cremonesi P., Casellato M. M., Antonini E. Enzymatic reactions in heterogeneous phase. Preparation of 5-androstene-3,17-dione. Steroids Lipids Res. 1974; 5: 162–166
   PubMedGoogle Scholar
• Carrea G., Riva S., Bovara R., Pasta P. Enzymatic oxidoreduction of steroids in two-phase systems: effects or organic solvents on enzyme kinetics and evaluation of the performance of different reactors. Enzvme Microb. Technol. 1988; 10: 333–340
   Web of Science ®Google Scholar
• Chenault H. K., Whitesides G. M. Regeneration of nicotinamide cofactors for use in organic synthesis. Appl. Biochem. Biotechnol. 1987; 14: 147–197
   PubMed Web of Science ®Google Scholar
• Cremonesi P., Carrea G, Ferrara L., Antonini E. Enzymatic dehydrogena-tion of testosterone coupled to pyruvate reduction in a two-phase system. Eur. J. Biochem. 1974; 44: 401–405
   PubMedGoogle Scholar
• Cremonesi P., Carrea G, Ferrara L., Antonini E. Enzymatic preparation of 20β-hydroxysteroids in a two-phase system. Biotechnol. Bioeng. 1975; 17: 1101–1108
   PubMed Web of Science ®Google Scholar
• Deetz J. S., Rozzell J. D. Enzymatic catalysis by alcohol dehydrogenases in organic solvents. Ann. N.Y. Acad. Sci. 1988; 542: 230–234
   Google Scholar
• Dominguez E., Lan H. L., Okamoto Y., Hale P. D., Skotheim T. A., Gorton L., Hahn-Hägerdal B. Reagentless chemically modified carbon paste electrode based on a phenothiazine polymer derivative and yeast alcohol dehydrogenase for the analysis of ethanol. Biosensors & Bioelectronics 1993; 8: 229–237
   Web of Science ®Google Scholar
• Freeman A., Lilly M. D. The effect of water-miscible solvents on the δ1-dehydrogenase activity of free and PAAH-entrapped. Arthrobacter simplex”. Appl. Microbiol. Biotechnol. 1987; 25: 495–501
   Web of Science ®Google Scholar
• Fukui S., Ahmed S. A., Omata T., Tanaka A. Bioconversion of lipophilic compounds in non-aqueous solvent. Effect of gel hydrophobicity on diverse conversons of testosterone by gel-entrapped Nocardia rhodocrous cells. Eur. J. Appl. Microbiol. Biotechnol. 1980; 10: 289–301
   Google Scholar
• Grunwald J., Wirz B., Scollar M. P., Klibanov A. M. Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents. J. Am. Chem. Soc. 1986; 108: 6732–6734
   Web of Science ®Google Scholar
• Hall G. F., Turner A. P. F. Electron transfer from diaphorase in water/Triton X-100/butyl acetate microemulsion. Electroanalysis 1994; 6: 217–220
   Web of Science ®Google Scholar
• Hilhorst R., Laane C., Veegers C. Photosensitized production of hydrogen by hydrogenase in reversed micells. Proc. Natl Acad. Sci. USA 1982; 79: 3927–3930
   PubMed Web of Science ®Google Scholar
• Hilhorst R., Laane C., Veeger C. Enzymatic conversion of apolar compounds in organic media using an NADH-regeneration system and dihydrogen as reductant. FEBS Lett. 1983; 159: 225–228
   Web of Science ®Google Scholar
• Hocknull M. D., Lilly M. D. Stability of the steroid δ1-dehydrogenation system of Arthrobacter simplex in organic solvent-water two-liquid phase environments. Enz. Microb. Technol. 1988; 10: 669–674
   Web of Science ®Google Scholar
• Howaldt M., Gottlob A., Kulbe K. D., Chmiel H. Simultaneous conversion of glucose/fructose mixtures in a membrane reactor. Ann. N.Y. Acad. Sci. 1988; 542: 400–405
   Google Scholar
• Itoh S., Terasaka T., Matsumiya M., Komatsu M., Ohshiro Y. Efficient NAD+-recycling system for ADH-catalysed oxidation in organic media. J. Chem. Soc. Perkin Trans. I 1992; 1992: 3253–3254
   Google Scholar
• Itozawa T., Kise H. Highly efficient regeneration system for reduction of cyclohexanone by horse liver alcohol dehydrogenase in organic solvent. Biotechnol. Lett. 1993; 15: 843–846
   Web of Science ®Google Scholar
• Itozawa T., Kise H. Immobilization of HLADH on polymer materials for reduction of cyclohexanone with NADH regeneration under two-phase conditions. J. Ferment. Bioeng. 1995; 80: 30–34
   Google Scholar
• Kawamoto T., Aoki A., Sonomoto K., Tanaka A. Novel photocatalytic NAD+ recycling system with a semiconductor in organic solvent. J. Ferment. Bioeng. 1989; 67: 361–362
   Google Scholar
• Khmelnitsky Y. L., Neverova I. N., Polyakov V. I., Grinberg V. Y., Levashov A. V., Martinek K. Kinetic theory of enzymatic reactions in reversed micellar systems. Application to the pseudophase approach for partitioning substrates. Eur. J. Biochem. 1990; 190: 155–159
   PubMedGoogle Scholar
• Klibanov A. M. Enzymes that work in organic solvents. Chemtech. 1986; 16.: 354–359
   Google Scholar
• Biocatalysis in organic media, C. Laane, J. Tramper, M. D. Lilly. Elsevier, Amsterdam 1987
   Google Scholar
• Laane C., Verhaert R. Photochemical, electrochemical, and hydrogen-driven enzymatic reductions in reversed micelles. Israel J. Chem. 1987/88; 28: 17–22
   Web of Science ®Google Scholar
• Larsson K., Adlercreutz P., Mattiasson B. Activity and stability of HLADH (horse liver alcohol dehydrogenase), in AOT-cyclohexane reverse micells. Eur. J. Biochem. 1987; 166: 157–161
   PubMedGoogle Scholar
• Larsson K., Janssen A., Adlercreutz P., Mattiasson B. Three systems used for biocatalysis in organic solvents - a comparative study. Biocatalysis. 1990; 4: 163–175
   Google Scholar
• Larsson K. M., Adlercreutz P., Mattiasson B. Enzymatic catalysis in microe-mulsions. Enzyme reuse and product recovery. Biotechnol. Bioeng. 1990; 36: 135–141
   PubMed Web of Science ®Google Scholar
• Larsson K. M., Adlercreutz P., Mattiasson B. Enzyme catalysis in uni and biocontinuous microemulsions: kinetics dependence on substrate partitioning. J. Chem. Soc. Faraday Trans. 1991; 87: 465–471
   Google Scholar
• Lee K. M., Biellmann J.-P. Enzyme and organic solvents: horse liver alcohol dehydrogenase in non-ionic microemulsion: stability and activity. FEBS Lett. 1987; 223: 33–36
   PubMed Web of Science ®Google Scholar
• Lee K. M., Blaghen M., Samama J.-P., Biellmann J.-F. Crosslinked crystaline horse liver alcohol dehydrogenase as a redox catalyst: activity and stability toward organic solvent. Bioorg. Chem. 1986; 14: 202–210
   Google Scholar
• Lee K. M., Martin D., Park C. U., Biellmann J.-F. Enzyme resolution of 1-formyl-trimethylenemethane-iron-tricarbonyl with horse liver alcohol dehydrogenase in microemulsion. Bull. Korean Chem. Soc. 1990; 11: 472–473
   Web of Science ®Google Scholar
• Lemière G. L., Lepoivre J. A., Alderweireldt F. C. Ring-size effects in horse liver alcohol dehydrogenase-catalyzed redox reactions. Bioorg. Chem. 1988; 16: 165–174
   Web of Science ®Google Scholar
• Lortie R., Villaume I., Legoy M. D., Thomas D. Enzymatic production of longchain aldehydes in a fixed bed reactor using organic solvents and cofactor regeneration. Biotechnol. Bioeng. 1989; 33: 229–232
   PubMed Web of Science ®Google Scholar
• Mansson M.-O., Larsson P.-O., Mosbach K. Covalent binding of an NAD+ analogue to liver alcohol dehydrogenase resulting in an enzyme-coenzyme complex not requiring exogeneous coenzyme for activity. Eur. J. Biochem. 1978; 86: 455–463
   PubMedGoogle Scholar
• Nikolova P., Goldman H., Ward O. P. Factors affecting catalytic performance in YADH-catalyzed reductions in non-conventional media. Can. J. Chem. Eng. 1995; 73: 510–515
   Web of Science ®Google Scholar
• Otamiri M., Adlercreutz P., Mattiasson B. Complex formation between chymotrypsin and ethyl cellulose as a means of solubilize the enzyme in active form in toluene. Biocatalysis. 1992; 6: 291–305
   Google Scholar
• Parida S., Datta R., Dordick J. Supported aqueous-phase enzymatic catalysis in organic media. Appl. Biochem. Biotechnol. 1992; 33: 1–14
   Web of Science ®Google Scholar
• Pinheiro H. M., Cabral J. M. S., Adlercreutz P. Quinones as external electron acceptors in steroid δ1-dehydrogenation with entrapped cells in organic medium. Biocatalysis. 1993; 7: 83–96
   Google Scholar
• Riddick J. A., Bunger W. B., Sakano T. K. Organic solvents. Physical properties and methods of purification. Wiley-Interscience, New York 1986
   Google Scholar
• Riva S., Bovara R., Zetta L., Pasta P., Ottolina G., Carrea G. Enzymatic a/β inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. J. Org. Chem. 1988; 53: 88–92
   Web of Science ®Google Scholar
• Samama J.-P., Lee K. M., Biellmann J.-P. Enzymes and microemulsions. Activity and kinetic properties of alcohol dehydrogenase in ionic water-in-oil microemulsions. Eur. J. Biochem. 1987; 163: 609–617
   PubMedGoogle Scholar
• Saini S., Hall G. F., Downs M. E. A., Turner A. P. F. Organic phase enzyme electrodes. Anal. Chim. Acta. 1991; 249: 1–15
   Web of Science ®Google Scholar
• Shimidzu S., Yamada H. Stereospecific reduction of 3–keto acid esters by a novel aldehyde reductase of Sporobolomyces salmonicolor in a water-organic solvent two-phasic system. Ann. N.Y. Acad. Sci. 1990; 613: 628–632
   Web of Science ®Google Scholar
• Simon H., Bader J., Güther H., Neumann S., Thanos J. Chiral compounds synthesized by biocatalytic reductions. Angew. Chem. Int. Ed. Engl. 1985; 24: 539–553
   Web of Science ®Google Scholar
• Snijder-Lambers A. M., Doddema H. J., Grande H. J., van Lelyveld P. H. Log P as a hydrophobicity index for biocatalysis; cofactor regeneration during enzymatic steroid oxidation in organic solvents. Biocatalysis in organic media, C. Laane, J. Tramper, M. D. Lilly. Elsevier, Amsterdam 1987; 87–95
   Google Scholar
• Snijder-Lambers A. M., Vulfson E. N., Doddema H. J. Optimization of alcohol dehydrogenase activity and NAD(H) regeneration in organic solvents. Recl. Trav. Chim. Pays-Bas. 1991; 110: 226–230
   Google Scholar
• Biocatalysis in non-conventional media, J. Tramper, M. H. Vermüe, H. H. Beeftink, U. von Stockar. Elsevier, Amsterdam 1992
   Google Scholar
• Valivety R. H., Halling P. J., Macrae A. R. Reaction rate with suspended lipase catalyst shows similar dependence on water activity in different organic solvents. Biochim. Biophys. Acta. 1992; 1118: 218–222
   PubMed Web of Science ®Google Scholar
• van Elsacker P. C., Lemière G. L., Lepoivre J. A., Alderweireldt F. C. The HLADH-catalyzed oxidoreduction in a two-phase system 'organic solvent-moistened glass beads'. Bioorg. Chem. 1989; 17: 28–35
   Web of Science ®Google Scholar
• Wichmann R., Wandrey C., Bückmann A., Kula M.-R. Continuous enzymatic transformation in an enzyme membrane reactor with simultaneous NAD(H) regeneration. Biotechnol. Bioeng. 1981; 23: 2789–2802
   Web of Science ®Google Scholar
• Virto C., Svensson I., Adlercreutz P., Mattiasson B. Catalytic activity of noncovalent complexes of horse liver alcohol dehydrogenase, NAD+ and polymers, dissolved or suspended in organic solvents. Biotechnol. Lett. 1995; 17: 877–882
   Web of Science ®Google Scholar
• Yamane T., Nakatani H., Sada E., Omata T., Tanaka A., Fukui S. Steroid bioconversion in water-insoluble organic solvents: δ1-dehydrogenation by free microbial cells and by cells entrapped in hydrophilic or lipophilic gels. Biotechnol. Bioeng. 1979; 21: 2133–2145
   Web of Science ®Google Scholar
• Yang F., Russell A. J. Two-step biocatalytic conversion of an ester to an aldehyde in reverse micelles. Biotechnol. Bioeng. 1994; 43: 232–241
   PubMed Web of Science ®Google Scholar
• Zaks A., Klibanov A. The effect of water on enzyme action in organic media. J. Biol. Chem. 1988; 263: 8017–8021
   PubMed Web of Science ®Google Scholar