Asymmetric enzymatic oxidoreductions in organic solvents

Current Opinion in Biotechnology

Volumn 14, Issue 4, 2003, Pages 427-431

  Klibanov, Alexander M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; ORGANIC SOLVENT; PEROXIDASE; SULFOXIDE; VEGETABLE PROTEIN;

ACIDITY; ALKALINITY; AQUEOUS SOLUTION; ASYMMETRIC CATALYSIS; BIOCATALYST; BIOTECHNOLOGY; CATALYST; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME CHEMISTRY; ENZYME CONFORMATION; ENZYME ENGINEERING; ENZYME STABILITY; ENZYME STRUCTURE; FREEZE DRYING; HYDROPHILICITY; MOLECULAR DYNAMICS; OXIDATION REDUCTION REACTION; PHYTOCHEMISTRY; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0042933786     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(03)00074-0     Document Type: Review

References (46)

1. Faber K: Biotransformations in Organic Chemistry, edn 4. Berlin: Springer-Verlag; 2000.
2. Schmid A., Dordick J.S., Hauer B., Kaener A., Wubbolts M., Witholt B. Industrial biocatalysis today and tomorrow. Nature. 409:2001;258-268.
3. Klibanov A.M. Improving enzymes by using them in organic solvents. Nature. 409:2001;241-246 Discussion and mechanistic analysis of novel properties exhibited by enzymes placed in neat nonaqueous solvents instead of water.
4. Carrea G., Riva S. Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Ed Engl. 39:2000;2227-2254.
5. Van Deurzen M.P.J., Van Rantwijk F., Sheldon R.A. Selective oxidations catalyzed by peroxidases. Tetrahedron. 54:1997;13183-13220.
6. Adam W., Lazarus M., Saha-Moller C.R., Weichold O., Hoch U., Haring D., Schreier P. Biotransformations with peroxidases. Adv Biochem Eng Biotechnol. 63:1999;73-108.
7. Colonna S., Gaggero N., Richelmi C., Pasta P. Recent biotechnological developments in the use of peroxidases. Trends Biotechnol. 17:1999;163-168.
8. Van de Velde F., Van Rantwijk F., Sheldon R.A. Improving the catalytic performance of peroxidases in organic synthesis. Trends Biotechnol. 19:2001;73-80.
9. Zaks A., Klibanov A.M. Enzymatic catalysis in organic media at 100°C. Science. 224:1984;1249-1251.
10. Zaks A., Klibanov A.M. The effect of water on enzyme action in organic media. J Biol Chem. 263:1988;8017-8021.
11. Dai L., Klibanov A.M. Striking activation of oxidative enzymes suspended in nonaqueous media. Proc Natl Acad Sci USA. 96:1999;9475-9478.
12. Klibanov A.M. Why are enzymes less active in organic solvents than in water? Trends Biotechnol. 15:1997;97-101.
13. Lee M.-Y., Dordick J.S. Enzyme activation for nonaqueous media. Curr Opin Biotechnol. 13:2002;376-384.
14. Narayan V.S., Klibanov A.M. Are water-immiscibility and apolarity of the solvent relevant to enzyme efficiency? Biotechnol Bioeng. 41:1993;390-393.
15. Griebenow K., Klibanov A.M. On protein denaturation in aqueous-organic mixtures but not in pure organic solvents. J Am Chem Soc. 118:1996;11695-11700.
16. Lapanje S: Physicochemical Aspects of Protein Denaturation. New York: Wiley; 1978.
17. Fersht A: Structure and Mechanism in Protein Science: a Guide to Enzyme Catalysis and Protein Folding. New York: Freeman; 1999.
18. Wescott C.R., Klibanov A.M. The solvent dependence of enzyme specificity. Biochim Biophys Acta. 1206:1994;1-9.
19. Klibanov A.M. Enzyme memory - what is remembered and why? Nature. 374:1995;596.
20. Rupley J.A., Careri G. Protein hydration and function. Adv Protein Chem. 41:1991;37-172.
21. Ozawa S., Klibanov A.M. Myoglobin-catalyzed epoxidation of styrene in organic solvents accelerated by bioimprinting. Biotechnol Lett. 22:2000;1269-1272.
22. Xie Y., Das P.K., Caaveiro J.M.M., Klibanov A.M. Unexpectedly enhanced stereoselectivity of peroxidase-catalyzed sulfoxidation in branched alcohols. Biotechnol Bioeng. 79:2002;105-111.
23. Agranat I., Caner H., Caldwell J. Putting chirality to work: the strategy of chiral switches. Nat Rev Drug Discov. 1:2002;753-768 A thorough and scholarly discussion of scientific, commercial, economic, regulatory, and legal aspects of replacing racemic drugs with their single-enantiomer versions.
24. Carreno M.C. Application of sulfoxides to asymmetric synthesis of biologically active compounds. Chem Rev. 95:1995;1717-1760.
25. Colonna S., Gaggero N., Carrea G., Pasta P. Horseradish peroxidase catalyzed sulfoxidation is enantioselective. J Chem Soc Chem Commun. 1:1992;357-358.
26. Blee E., Schuber F. Mechanism of S-oxidation reactions catalyzed by soybean hydroperoxide-dependent oxygenase. Biochemistry. 28:1989;4962-4967.
27. Colonna S., Gaggero N., Richelmi C., Carrea G., Pasta P. Enantioselective sulfoxidations catalyzed by lactoperoxidase. Gazzetta Chim Ital. 125:1995;479-482.
28. Colonna S., Gaggero N., Carrea G., Pasta P. The microperoxidase-catalyzed oxidation of sulfides is enantioselective. Tetrahedron Lett. 35:1994;9103-9104.
29. Colonna S., Gaggero N., Manfredi A., Casella L., Gullotti M., Carrea G., Pasta P. Enantioselective oxidation of sulfides catalyzed by chloroperoxidase. Biochemistry. 29:1990;10465-10468.
30. Dai L., Klibanov A.M. Peroxidase-catalyzed asymmetric sulfoxidation in organic solvents versus in water. Biotechnol Bioeng. 70:2000;353-357.
31. Das P.K., Caaveiro J.M.M., Luque S., Klibanov A.M. Binding of hydrophobic hydroxamic acids enhances peroxidase's stereoselectivity in nonaqueous sulfoxidations. J Am Chem Soc. 124:2002;782-787 Discovery and structure-based molecular modeling explanation of how aromatic hydroxamic acids improve the stereoselectivity of horseradish peroxidase in the oxidation of organic sulfides into chiral sulfoxides in methanol.
32. Grunwald J., Wirz B., Scollar M.P., Klibanov A.M. Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents. J Am Chem Soc. 108:1986;6732-6734.
33. Kazandjian R.Z., Klibanov A.M. Regioselective oxidation of phenols catalyzed by polyphenol oxidase in chloroform. J Am Chem Soc. 107:1985;5448-5450.
34. Dordick J.S., Marletta M.A., Klibanov A.M. Polymerization of phenols catalyzed by peroxidase in nonaqueous media. Biotechnol Bioeng. 30:1987;31-36.
35. Akkara J.A., Ayyagari M.S., Bruno F.F. Enzymatic synthesis and modification of polymers in nonaqueous solvents. Trends Biotechnol. 17:1999;67-73.
36. Kazandjian R.Z., Dordick J.S., Klibanov A.M. Enzymatic analyses in organic solvents. Biotechnol Bioeng. 28:1986;417-421.
37. Boeriu C.G., Dordick J.S., Klibanov A.M. Enzymatic reactions in liquid and solid paraffins: application for enzyme-based temperature abuse sensors. Biol Technol. 4:1986;997-999.
38. Hinckley G., Mozhaev V.V., Budde C., Khmelnitsky Y.L. Oxidative enzymes possess catalytic activity in systems with ionic liquids. Biotechnol Lett. 24:2002;2083-2087.
39. Hammond D.A., Karel M., Klibanov A.M., Krukonis V.J. Enzymatic reactions in supercritical gases. Appl Biochem Biotechnol. 11:1985;393-400.
40. Randolph T.W., Clark D.S., Blanch H.W., Prausnitz J.M. Enzymatic oxidation of cholesterol aggregates in supercritical carbon dioxide. Science. 239:1988;387-390.
41. Barzana E. Gas phase biosensors. Adv Biochem Eng Biotechnol. 53:1995;1-15.
42. Barzana E., Klibanov A.M., Karel M. A colorimetric method for enzymatic analysis of gases: the determination of ethanol and formaldehyde vapors using solid alcohol oxidase. Anal Biochem. 182:1989;109-115.
43. Margolin A.L., Navia M.A. Protein crystals as novel catalytic materials. Angew Chem Int Ed Engl. 40:2001;2204-2222 An insightful review of biotechnological uses of (cross-linked) enzyme crystals as opposed to dissolved or lyophilized enzymes.
44. Farinas E.T., Butler T., Arnold F.H. Directed enzyme evolution. Curr Opin Biotechnol. 12:2001;545-551.
45. Mabrouk 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. 117:1995;2141-2146.
46. Shelimov K.B., Clemmer D.E., Hudgins R.R., Jarrold M.F. Protein structure in vacuo: gas-phase conformations of BPTI and cytochrome c. J Am Chem Soc. 119:1997;2240-2248.