Low operational stability of enzymes in dry organic solvents: Changes in the active site might affect catalysis

Molecules

Volumn 17, Issue 2, 2012, Pages 1870-1882

  Bansal, Vibha ^a   Delgado, Yamixa ^b   Legault, Marc D ^c   Barletta, Gabriel ^b  

^a UNIVERSITY OF PUERTO RICO AT CAYEY   (Puerto Rico)

^b UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

Enzyme kinetics in organic solvents; EPR spectroscopy; Organic solvents; Subtilisin Carlsberg

Indexed keywords

ENZYME; SOLVENT;

ARTICLE; BIOCATALYSIS; CHEMISTRY; ELECTRON SPIN RESONANCE; ENZYME ACTIVE SITE; ENZYME STABILITY; KINETICS; METABOLISM; SPIN LABELING;

BIOCATALYSIS; CATALYTIC DOMAIN; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENZYME STABILITY; ENZYMES; KINETICS; SOLVENTS; SPIN LABELS;

EID: 84857565253     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17021870     Document Type: Article

References (35)

1. Effenberger, F.; Syed, J. Stereoselective synthesis of biologically active tetronic acids. Tetrahedron 1998, 9, 817-825. (Pubitemid 28172354)
2. Jungen, M.; Gais, H. Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives. Tetrahedron-Asymmetry 1999, 10, 3747-3758. (Pubitemid 30009578)
3. Klibanov, A.M. Improving enzymes by using them in organic solvents. Nature 2001, 409, 241-246. (Pubitemid 32144293)
4. Lee, T.; Jones, J.B. Probing the abilities of synthetically useful serine proteases to discriminate between the configurations of remote stereocenters using chiral aldehyde inhibitors. J. Am. Chem. Soc. 1996, 118, 502-508. (Pubitemid 26052033)
5. Macritchie, J.A.; Silcock, A.; Willis, C.L. Enantioselective synthesis of unsaturated α-hydroxy acids. Tetrahedron: Asymmetry 1997, 8, 3895-3902. (Pubitemid 28013006)
6. Roberts, S.M.; Williamson, N.M. The use of enzymes for the preparation of biologically active natural products and analogues in optically active form. Curr. Org. Chem. 1997, 1, 1-20. (Pubitemid 127681625)
7. Sanchez, V.M.; Rebolledo, F.; Gotor, V. Candida antarctica lipase-catalyzed doubly enantioselective aminolysis reactions. Chemoenzymatic synthesis of 3-hydroxypyrrolidines and 4-(silyloxy)-2- oxopyrrolidines with two stereogenic centers. J. Org. Chem. 1999, 64, 1464-1470.
8. Zaks, A.; Klibanov, A.M. Enzymatic catalysis in nonaqueous solvents. J. Biol. Chem. 1988, 263, 3194-3201.
9. Carrea, G.; Riva, S. Properties and synthetic applications of enzymes in organic solvents. Angew. Chem. Int. Edit. 2000, 39, 2226-2254.
10. DeSantis, G.; Davis, B.G. The expanding roles of biocatalysis and biotransformation. Curr. Opin. Chem. Biol. 2006, 10, 139-140.
11. Fitzpatrick, P.A.; Steinmetz, A.C.U.; Ringe, D.; Klibanov, A.M. Enzyme crystal structure in a neat organic solvent. Proc. Natl. Acad. Sci. USA 1993, 90, 8653-8657. (Pubitemid 23277728)
12. Griebenow, K.; Klibanov, A.M. Lyophilization-induced reversible changes in the secondary structure of proteins. Proc. Natl. Acad. Sci. USA 1995, 92, 10969-10976.
13. Martinez, S.G.; Alvira, E.; Cordero, L.V.; Ferrer, A.; Montanes-Clemente, I.; Barletta, G. High initial activity but low storage stability observed for several preparations of subtilisin carslberg suspended in organic solvents. Biotechnol. Progr. 2002, 18, 1462-1466. (Pubitemid 35450910)
14. Columbus, L.; Hubbell, W.L. Mapping backbone dynamics in solution with site-directed spin labeling: Gcn4-58 bzip free and bound to DNA. Biochemistry 2004, 43, 7273-7287. (Pubitemid 38745748)
15. Columbus, L.; Kálai, T.; Jekö, J.; Hideg, K.; Hubbell, W.L. Molecular motion of spin labeled side chains in α-helices: Analysis by variation of side chain structure. Biochemistry 2001, 40, 3828-3846. (Pubitemid 32280420)
16. Clark, D.S. Characteristics of nearly dry enzymes in organic solvents: Implications for biocatalysis in the absence of water. Phil. Trans. R. Soc. Lond. B 2004, 359, 1299-1307. (Pubitemid 39123219)
17. Lietzow, M.A.; Hubbell, W.L. Motion of spin label side chains in cellular retinol-binding protein: Correlation with structure and nearest-neighbor interactions in an antiparallel β-sheet. Biochemistry 2004, 43, 3137-3151. (Pubitemid 38352264)
18. Ueji, S.; Taniguchi, T.; Okamoto, T.; Watanabe, K.; Ebara, Y.; Ohta, H. Flexibility of lipase brought about by solvents controls its enantioselectivity in organic media. Bull. Chem. Soc. Jpn. 2003, 76, 399-403. (Pubitemid 36402330)
19. Watanabe, K.; Yoshida, T.; Ueji, S. The role of conformation flexibility on enzymes in the diecrimination between amino acid and ester substrates for the subtilisin-catalyzed reaction in organic solvents. Bioorg. Chem. 2004, 32, 504-515. (Pubitemid 39504945)
20. Castillo, B.; Bansal, V.; Ganesan, A.; Halling, P.; Secundo, F.; Ferrer, A.; Griebenow, K.; Barletta, G. On the activity loss of hydrolases in organic solvents: II. A mechanistic study of subtilisin carlsberg. BMC Biotechnol. 2006, 6, doi:10.1186/1472-6750-6-51. (Pubitemid 46178899)
21. Castillo, B.; Pacheco, Y.; Al-Azzam, W.; Griebenow, K.; Devi, M.; Ferrer, A.; Barletta, G. On the activity loss of hydrolases in organic solvents: I. Rapid loss of activity of a variety of enzymes and formulations in a range of organic solvents. J. Mol. Catal. B-Enzym. 2005, 35, 147-153. (Pubitemid 41557497)
22. Castillo, B.; Sola, R.J.; Ferrer, A.; Barletta, G.; Griebenow, K. Effect of peg modification on subtilisin carlsberg activity, enantioselectivity, and structural dynamics in 1,4-dioxane. Biotechnol. Bioeng. 2008, 99, 9-17.
23. Fernandez, J.F.A.; Halling, P. Operational stability of high initial activity protease catalysts in organic solvents. Biotechnol. Progr. 2002, 18, 1455-1457. (Pubitemid 35450908)
24. Fasoli, E.; Ferrer, A.; Barletta, G.L. Hydrogen/deuterium exchange study of subtilisin carlsberg during prolonged exposure to organic solvents. Biotechnol. Bioeng. 2009, 102, 1025-1032.
25. Bansal, V.; Delgado, Y.; Fasoli, E.; Ferrer, A.; Griebenow, K.; Secundo, F.; Barletta, G.L. Effect of prolonged exposure to organic solvents on the active site environment of subtilisin carlsberg. J. Mol. Catal. B-Enzym. 2010, 64, 38-44.
26. Watanabe, K.; Yoshida, T.; Ueji, S. Optimum conformational flexibility of subtilisin to maximixe the enantioselectivity for subtilisin-catalysed transesterification in an organic solvent with an addition of dimethyl sulfoxide. Chem. Commun. 2001, 1260-1261. (Pubitemid 32664671)
27. Guo, Z.; Cascio, D.; Hideg, K.; Kálái, T.; Hubbell, W.L. Structural determinants of nitroxide motion in spin-labeled proteins: Tertiary contact and solvent-inaccessible sites in helix g of t4 lysozyme. Protein Sci. 2007, 16, 1069-1086. (Pubitemid 46849217)
28. Cruz, A.; Ramirez, E.; Santana, A.; Barletta, G.; Lopez, G. Molecular dynamic study of subtilisin carlsberg in aqueous and nonaqueous solvents. Mol. Simulat. 2009, 1-8.
29. Habeeb, A.F.S.A.; Cassidy, H.G.; Singer, S.J. Molecular structural effects produced in proteins by reaction with succinic anhydride. Biochim. Biophys. Acta 1958, 29, 587-593.
30. Schonbaum, G.R.; Zerner, B.; Bender, M.L. The spectrophotometric determination of the operational normality of an alpha-chymotrypsin solution. J. Biol. Chem. 1961, 236, 2930-2935.
31. Hubbell, W.L.; Cafiso, D.S.; Altenbach, C. Identifying conformational changes with site-directed spin labeling. Nat. Struct. Biol. 2000, 7, 735-739.
32. Hamilton, C.L.; McConney, H.M. Spin Labels. In Structural Chemistry and Molecular Biology, Rich, A., Davidson, N.R., Eds.; W.H. Freeman and Company: New York, NY, USA, 1968; p. 115.
33. Griebenow, K.; Laureano, Y.; Santos, A.M.; Montanez Clemente, I.; Rodriguez, L.; Vidal, M.W.; Barletta, G. Improved enzyme activity and enantioselectivity in organic solvents by methyl-β- cyclodextrin. J. Am. Chem. Soc. 1999, 121, 8157-8163.
34. Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W.H. Freeman and Company: New York, NY, USA, 1985.
35. Smith, P.K.; Krohn, R.I.; Hermanson, G.T.; Mallia, A.K.; Gartner, F.H.; Provenzano, M.D.; Fujimoto, E.K.; Goeke, N.M.; Olson, B.J.; Klenk, D.C. Measurement of protein using bicinchoninic acid. Anal. Biochem. 1985, 150, 76-85. (Pubitemid 16258399)