Improving enzymes by using them in organic solvents (original) (raw)
Roberts, S. M., Turner, N. J., Willetts, A. J. & Turner, M. K. Introduction to Biocatalysis Using Enzymes and Microorganisms (Cambridge Univ. Press, New York, 1995). Book Google Scholar
Faber, K. Biotransformations in Organic Chemistry 4th edn (Springer, Berlin, 2000). Book Google Scholar
Zaks, A. & Dodds, D. R. Application of biocatalysis and biotransformations to the synthesis of pharmaceuticals. Drug Disc. Today2, 513–531 ( 1997). ArticleCAS Google Scholar
Stinson, S. C. Counting on chiral drugs. Chem. Eng. News76, 83–96 (1998). Article Google Scholar
Nelson, D. L. & Cox, M. M. Lehninger Principles of Biochemistry 3rd edn, 192 (Worth, New York, 2000). Google Scholar
Lapanje, S. Physicochemical Aspects of Protein Denaturation Chs 1–3 & 6 (Wiley, New York, 1978). Google Scholar
Griebenow, K. & Klibanov, A. M. On protein denaturation in aqueous-organic mixtures but not in pure organic solvents. J. Am. Chem. Soc.47, 11695–11700 (1996). Article Google Scholar
Kuntz, I. D. & Kauzmann, W. Hydration of proteins and polypeptides . Adv. Protein Chem.28, 239– 345 (1974). ArticleCAS Google Scholar
Rupley, J. A. & Careri, G. Protein hydration and function. Adv. Protein Chem.41, 37–172 (1991). ArticleCAS Google Scholar
Fitzpatrick, P. A., Steinmetz, A. C. U., Ringe, D. & Klibanov, A. M. Enzyme crystal structure in a neat organic solvent. Proc. Natl Acad. Sci. USA90, 8653–8657 (1993). ArticleADSCAS Google Scholar
Yennawar, N. H., Yennawar, H. P. & Farber, G. K. X-ray crystal structure of γ-chymotrypsin in hexane. Biochemistry33, 7326– 7337 (1994). ArticleCAS Google Scholar
Schmitke, J. L., Stern, L. J. & Klibanov, A. M. Crystal structure of subtilisin Carlsberg in anhydrous dioxane and its comparison with those in water and acetonitrile. Proc. Natl Acad. Sci. USA94, 4250– 4255 (1997). ArticleADSCAS Google Scholar
Zhu, G. et al. X-ray studies on two forms of bovine β-crystals in neat cyclohexane . Biochim. Biophys. Acta1429, 142– 150 (1998). ArticleCAS Google Scholar
Gao, X.-G. et al. Crystal structure of triosephosphate isomerase from Trypanosoma cruzi in hexane. Proc. Natl Acad. Sci. USA96, 10062–10067 (1999). ArticleADSCAS Google Scholar
Klibanov, A. M. Enzymatic catalysis in anhydrous organic solvents. Trends Biochem. Sci.14, 141–144 ( 1989). ArticleCAS Google Scholar
Koskinen, A. M. P. & Klibanov, A. M. (eds) Enzymatic Reactions in Organic Media (Blackie-Pergamon, London, 1996). Book Google Scholar
Zaks, A. & Klibanov, A. M. Enzyme-catalyzed processes in organic solvents. Proc. Natl Acad. Sci. USA82, 3192–3196 (1985). ArticleADSCAS Google Scholar
Klibanov, A. M. Why are enzymes less active in organic solvents than in water? Trends Biotechnol.15, 97–101 (1997). ArticleCAS Google Scholar
Schmitke, J. L., Wescott, C. R. & Klibanov, A. M. The mechanistic dissection of the plunge in enzymatic activity upon transition from water to anhydrous solvents. J. Am. Chem. Soc.118, 3360–3365 (1996). ArticleCAS Google Scholar
Zaks, A. & Klibanov, A. M. Enzymatic catalysis in non-aqueous solvents J. Biol. Chem.263, 3194– 3201 (1988). CASPubMed Google Scholar
Xu, K. & Klibanov, A. M. pH-control of the catalytic activity of cross-linked enzyme crystals in organic solvents. J. Am. Chem. Soc.118, 9815–9819 (1996). ArticleCAS Google Scholar
Blackwood, A. D., Curran, L. J., Moore, B. D. & Halling, P. J. Organic-phase buffers control biocatalyst activity independent of initial aqueous pH. Biochim. Biophys. Acta1206, 161–165 (1994). ArticleCAS Google Scholar
Griebenow, K. & Klibanov, A. M. Can conformational changes be responsible for solvent and excipient effects on the catalytic behavior of subtilisin Carlsberg in organic solvents? Biotechnol. Bioeng.53, 351–362 (1997). ArticleCAS Google Scholar
Griebenow, K. & Klibanov, A. M. Lyophilization-induced changes in the secondary structure of proteins. Proc. Natl Acad. Sci. USA92, 10969–10976 ( 1995). ArticleADSCAS Google Scholar
Dabulis, K. & Klibanov, A. M. Dramatic enhancement of enzymatic activity in organic solvents by lyoprotectants. Biotechnol. Bioeng.41, 566–571 ( 1993). ArticleCAS Google Scholar
Dai, L. & Klibanov, A. M. Striking activation of oxidative enzymes suspended in nonaqueous media. Proc. Natl. Acad. Sci. USA96, 9475–9478 ( 1999). ArticleADSCAS Google Scholar
Khmelnitsky, Y. L., Welch, S. H., Clark, D. S. & Dordick, J. S. Salts dramatically enhance activity of enzymes suspended in organic solvents . J. Am. Chem. Soc.116, 2647– 2648 (1994). ArticleCAS Google Scholar
Russell, A. J. & Klibanov, A. M. Inhibitor-induced enzyme activation in organic solvents. J. Biol. Chem.263, 11624–11626 (1988). CASPubMed Google Scholar
Broos, J., Sakodinskaya, I. K., Engbersen, J. F. J., Verboom, W. & Reinhoudt, D. N. Large activation of serine proteases by pretreatment with crown ethers. J. Chem. Soc. Chem. Commun. 255–256 (1995).
Okahata, Y. & Mori, T. Lipid-coated enzymes as efficient catalysts in organic media. Trends Biotechnol.15, 50–54 (1997). ArticleCAS Google Scholar
Paradkar, V. M. & Dordick, J. S. Aqueous-like activity of α-chymotrypsin dissolved in nearly anhydrous organic solvents . J. Am. Chem. Soc.116, 5009– 5010 (1994). ArticleCAS Google Scholar
Margolin, A. L. Novel crystalline catalysts. Trends Biotechnol.14, 223–230 (1996). ArticleCAS Google Scholar
Jeffrey, J. A. & Saenger, W. Hydrogen Bonding in Biological Structures (Springer, Berlin, 1994). Google Scholar
Affleck, R., Haynes, C. A. & Clark, D. S. Solvent dielectric effects on protein dynamics. Proc. Natl Acad. Sci. USA89, 5167– 5170 (1992). ArticleADSCAS Google Scholar
Burke, P. A., Griffin, R. G. & Klibanov, A. M. Solid-state nuclear magnetic resonance investigation of solvent dependence of tyrosyl ring motion in an enzyme. Biotechnol. Bioeng.42, 87–94 ( 1993). ArticleCAS Google Scholar
Zaks, A. & Klibanov, A. M. The effect of water on enzyme action in organic media. J. Biol. Chem.263, 8017–8021 (1988). CASPubMed Google Scholar
Xu, Z.-F. et al. Transition state stabilization of subtilisins in organic media . Biotechnol. Bioeng.43, 515– 520 (1994). ArticleCAS Google Scholar
Bell, G., Halling, P. J., Moore, B. D., Partridge, J. & Rees, D. G. Biocatalyst behaviour in low-water systems. Trends Biotechnol.13, 468– 473 (1995). ArticleCAS Google Scholar
Almarsson, Ö. & Klibanov, A. M. Remarkable activation of enzymes in nonaqueous media by denaturing organic cosolvents . Biotechnol. Bioeng.49, 87– 92 (1996). ArticleCAS Google Scholar
Ahern, T. J. & Klibanov, A. M. Analysis of processes causing thermal inactivation of enzymes. Methods Biochem. Anal.33, 91–127 (1987). Google Scholar
Zaks, A. & Klibanov, A. M. Enzymatic catalysis in organic media at 100 °C. Science224, 1249– 1251 (1984). ArticleADSCAS Google Scholar
Volkin, D. B., Staubli, A., Langer, R. & Klibanov, A. M. Enzyme thermoinactivation in anhydrous organic solvents. Biotechnol. Bioeng.37, 843–853 (1991). ArticleCAS Google Scholar
Garza-Ramos, G., Darszon, A., de Gómez-Puyou, M. T. & Gómez-Puyou, A. Enzyme catalysis in organic solvents with low water content at high temperatures. The ATPase of submitochondrial particles. Biochemistry29, 751–757 (1990). ArticleCAS Google Scholar
Fersht, A. Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding (Freeman, New York, 1999). Google Scholar
Wescott, C. R. & Klibanov, A. M. The solvent dependence of enzyme specificity. Biochim. Biophys. Acta1206, 1–9 (1994). ArticleCAS Google Scholar
Carrea, G., Ottolina, G. & Riva, S. Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol.13, 63–70 (1995). ArticleCAS Google Scholar
Zaks, A. & Klibanov A. M. Substrate specificity of enzymes in organic solvents vs. water is reversed. J. Am. Chem. Soc.108, 2767–2768 ( 1986). ArticleCAS Google Scholar
Wescott, C. R. & Klibanov, A. M. Solvent variation inverts substrate specificity of an enzyme. J. Am. Chem. Soc.115, 1629–1631 (1993). ArticleCAS Google Scholar
Gaertner, H. & Puigserver, A. Kinetics and specificity of serine proteases in peptide synthesis catalyzed in organic solvents. Eur. J. Biochem.181, 207–213 (1989). ArticleCAS Google Scholar
Ryu, K. & Dordick, J. S. How do organic solvents affect peroxidase structure and function? Biochemistry31, 2588–2598 (1992). ArticleCAS Google Scholar
Wescott, C. R., Noritomi, H. & Klibanov, A. M. Rational control of enzymatic enantioselectivity through solvation thermodynamics. J. Am. Chem. Soc.118, 10365–10370 (1996). ArticleCAS Google Scholar
Ke, T., Wescott, C. R. & Klibanov, A. M. Prediction of the solvent dependence of enzymatic prochiral selectivity by means of structure-based thermodynamic calculations . J. Am. Chem. Soc.118, 3366– 3374 (1996). ArticleCAS Google Scholar
Wu, S.-H., Chu, F.-Y. & Wang, K.-T. Reversible enantioselectivity of enzymatic reactions by media. Bioorg. Med. Chem. Lett.1, 339– 342 (1991). ArticleADSCAS Google Scholar
Ueji, S. et al. Solvent-induced inversion of enantioselectivity in lipase-catalyzed esterification of 2-phenoxypropionic acids. Biotechnol. Lett.14, 163–168 (1992). ArticleCAS Google Scholar
Tawaki, S. & Klibanov, A. M. Inversion of enzyme enantioselectivity by the solvent. J. Am. Chem. Soc.114, 1882 –1884 (1992). ArticleCAS Google Scholar
Rubio, E., Fernandes-Mayorales, A. & Klibanov, A. M. Effect of the solvent on enzyme regioselectivity . J. Am. Chem. Soc.113, 695– 696 (1991). ArticleCAS Google Scholar
MacManus, D. A. & Vulfson, E. N. Reversal of regioselectivty in the enzymatic acylation of secondary hydroxyl groups mediated by organic solvents. Enzyme Microb. Technol.20, 225–228 (1997). ArticleCAS Google Scholar
Tawaki, S. & Klibanov, A. M. Chemoselectivity of enzymes in anhydrous media is strongly solvent dependent. Biocatalysis8, 3–19 (1993 ). ArticleCAS Google Scholar
Ebert, C., Gardossi, L., Linda, P., Vesnaver, R. & Bosco, M. Influence of organic solvents on enzyme chemoselectivity and their role in enzyme-substrate interaction. Tetrahedron52, 4867–4876 (1996). ArticleCAS Google Scholar
Ke, T. & Klibanov, A. M. On enzymatic activity in organic solvents as a function of enzyme history. Biotechnol. Bioeng.57, 746–750 (1998). ArticleCAS Google Scholar
Rich, J. O. & Dordick, J. S. Controlling subtilisin activity and selectivity in organic media by imprinting with nucleophilic substrates . J. Am. Chem. Soc.119, 3245– 3252 (1997). ArticleCAS Google Scholar
Stahl, M., Jeppson-Wistrand, U., Mansson, M.-O. & Mosbach, K. Induced stereoselectivity and substrate selectivity of bio-imprinted α-chymotrypsin in anhydrous organic media. J. Am. Chem. Soc.113, 9366–9368 (1991). Article Google Scholar
Mingarro, I., González-Navarro, H. & Braco, L. Trapping of different lipase conformers in water-restricted environments. Biochemistry35, 9935–9944 (1996). ArticleCAS Google Scholar
Johnson, D. V. & Griengl, H. Biocatalytic applications of hydroxynitrile lyases. Adv. Biochem. Eng. Biotechnol.63, 31–55 (1999). CAS Google Scholar
Ke, T. & Klibanov, A. M. Markedly enhancing enzymatic enantioselectivity in organic solvents by forming substrate salts. J. Am. Chem. Soc.121, 3334–3340 (1999). ArticleCAS Google Scholar
Chen, C.-S., Fujimoto, Y., Girdaukas, G. & Sih, C. J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc.104, 7294–7299 (1982). ArticleCAS Google Scholar
Bornscheuer, U. T. & Kazlauskas, R. J. Hydrolases in Organic Synthesis—Regio- and Stereoselective Biotransformations (Wiley, Weinheim, 1999). Google Scholar
Kirchner, G., Scollar, M. P. & Klibanov, A. M. Resolution of racemic mixtures via lipase catalysis in organic solvents. J. Am. Chem. Soc.107, 7072–7076 (1985). ArticleCAS Google Scholar
Carrea, G. & Riva, S. Properties and synthetic applications of enzymes in organic solvents. Angew. Chem.33, 2226–2254 (2000). Article Google Scholar
Kitaguchi, H., Fitzpatrick, P. A., Huber, J. E. & Klibanov, A. M. Enzymatic resolution of racemic amines: crucial role of the solvent J. Am. Chem. Soc.111, 3094–3095 (1989). ArticleCAS Google Scholar
Gutman, A. L., Meyer, E., Kalerin, E., Polyak, F. & Sterling, J. Enzymatic resolution of racemic amines in a continuous reactor in organic solvents. Biotechnol. Bioeng.40 , 760–767 (1992). ArticleCAS Google Scholar
Akkara, J. A., Ayyagari, M. S. R. & Bruno, F. F. Enzymatic synthesis and modification of polymers in nonaqueous solvents. Trends Biotechnol.17, 67–73 (1999). ArticleCAS Google Scholar
Chaudhary, A. K., Beckman, E. J. & Russell, A. J. Rational control of polymer molecular weight and dispersity during enzyme-catalyzed polyester synthesis in supercritical fluids . J. Am. Chem. Soc.117, 3728– 3733 (1995). ArticleCAS Google Scholar
Barzana, E., Karel, M. & Klibanov, A. M. A colorimetric method for the enzymatic analysis of gases: the determination of ethanol and formaldehyde vapors using solid alcohol oxidase. Anal. Biochem.182, 109 –115 (1989). ArticleCAS Google Scholar
Marbrouk, P. A. The use of nonaqueous media to prove biochemically significant enzyme intermediates: the generation and stabilization of horseradish peroxidase compound III in neat benzene solution at room temperature. J. Am. Chem. Soc.117, 2141–2146 (1995). Article Google Scholar
Michels, P. C., Dordick, J. S. & Clark, D. S. Dipole formation and solvent electrostriction in subtilisin catalysis. J. Am. Chem. Soc.119, 70–76 (1997). Article Google Scholar
Barzana, E. Gas phase biosensors. Adv. Biochem. Eng. Biotechnol.53, 1–15 (1995). Article Google Scholar
Gill, I. & Vulfson, E. Enzymic catalysis in heterogeneous eutectic mixtures of substrates. Trends Biotechnol.12, 118–122 (1994). ArticleCAS Google Scholar
De Bont, J. A. M. Solvent-tolerant bacteria in biocatalysis. Trends Biotechnol.16, 493–499 (1998). ArticleCAS Google Scholar