High initial activity but low storage stability observed for several preparations of subtilisin carslberg suspended in organic solvents

Biotechnology Progress

Volumn 18, Issue 6, 2002, Pages 1462-1466

  González Martínez, Susimar ^a   Alvira, Edgardo ^a   Vergara Cordero, Liz ^a   Ferrer, Amaris ^a   Montañés Clemente, Ileana ^a   Barletta, Gabriel ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

INCUBATION;

CROSSLINKING; CRYSTALS; ENZYMES; ORGANIC SOLVENTS;

BIOTECHNOLOGY;

ENZYME STABILITY; FREEZE DRYING; HALF-LIFE; PRESERVATION, BIOLOGICAL; SOLVENTS; SUBTILISIN; TIME FACTORS;

EID: 0036862312     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp025650g     Document Type: Article

References (25)

1. Effenberger, F.; Syed, J. Stereoselective synthesis of biologically active tetronic acids. Tetrahedron 1998, 9, 817-825.
2. Jungen, M.; Gais, H. Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives. Tetrahedron 1999, 10, 3747-3758.
3. Klibanov, A. M. Asymmetric transformations catalyzed by enzymes in organic solvents. Acc. Chem. Res. 1990, 23, 114-120.
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.
5. Macritchie, J. A.; Silcock, A.; Willis, C. L. Enantioselective synthesis of unsaturated α-hydroxy acids. Tetrahedron: Asymmetry 1997, 8, 3895-3902.
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.
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. Altreuter, D. H.; Dordick, J. S.; Clark, D. S. Nonaqueous biocatalytic synthesis of new cytotoxic dozorubicin derivatives: Exploiting unexpected differences in the regioselectivity of salt-activated and solubilized subtilisin. J. Am. Chem. Soc. 2002, 124, 1871-1876.
10. 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. 1996, 118, 3360-3365.
11. Dabulis, K.; Klibanov, A. M. Dramatic enhancement of enzyme activity in organic solvents by lyoprotectants. Biothechnol. Bioeng. 1993, 41, 566-571.
12. Hyeong Kwon, O.; Imanishi, Y.; Ito, Y. Enhancement of catalytic activity of chemically modifed subtilisin carlsberg in benzene by adjustment of lyophilization conditions. Bull. Chem. Soc. Jpn. 2000, 73, 1277-1282.
13. Ke, T.; Klibanov, A. M. Markedly enhancing enzymatic enantioselectivity in organic solvents by forming substrate salts. J. Am. Chem. Soc. 1999, 121, 3334-3340.
14. Slade, C. J.; Vulfson, E. N. Induction of catalytic activity in proteins by lyophilization in the presence of a transition state analogue. Biotechnol. Bioeng. 1998, 57, 211-215.
15. Xu, K.; Klibanov, A. M. pH control of the catalytic activity of cross-linked enzyme crystals in organic solvents. J. Am. Chem. Soc. 1996, 118, 9815-9819.
16. 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.
17. Santos, A. M.; Vidal, M.; Pacheco, Y.; Frontera, C. B.; Ornellas, O.; Barletta, G.; Griebenow, K. Effect of crown ethers on structure, stability, activity and enantioselectivity of subtilisin Carlsberg in organic solvents. Biotechnol. Bioeng. 2001, 74, 295-308.
18. Griebenow, K.; Vidal, M.; BaÉz, C.; Santos, A.; Barletta, G. Nativelike enzyme properties are important for optimum activity in neat organic solvents. J. Am. Chem. Soc. 2001, 123, 5380-5381.
19. Van Unen, D.; Engbersen, J. F. J.; Reinhoudt, D. N. Why do crown ethers activate enzymes in organic solvents? Biotechnol. Bioeng. 2002, 77, 248-255.
20. Santos, A. M.; Montañes-Clemente, I.; Barletta, G.; Griebenow, K. Activation of serine protease subtilisin carlsberg in organic solvents: Combined effect of methyl-β-cyclodextrin and water. Biotechnol. Lett. 1999, 21, 1113-1118.
21. Montañes-Clemente, I.; Alvira, A.; Macias, M.; Ferrer, A.; Fonceca, M. Rodriguez, J.; Gonzalez, A.; Barletta, G. Enzyme activation in organic solvents: Colyophilization of subtilisin carlsberg with methyl-β-cyclodextrin renders an enzyme catalyst more active than the cross-linked enzyme crystals. Biotechnol. Bioeng. 2002, 78, 53-59.
22. Fersht, A. Enzyme Structure and Mechanism; Freeman and Company: San Francisco, 1985.
23. Griebenow, K.; Klibanov, A. M. On protein denaturation in aqueous-organic mixtures but not in pure organic solvents. J. Am. Chem. Soc. 1996, 118, 1195-11700.
24. Wangikar, P. P.; Michels, P. C.; Clark, D. S.; Dordick, J. S. Structure and function of subtilisin BPN' solubilized in organic solvents. J. Am. Chem. Soc. 1997, 119, 70-76.
25. Fitzpatrick, P. A.; Steinmetz, A. C. U.; Ringe, D.; Klibanov, A. M. Enzyme crystal structure in a neat organic solvent. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8653-8657.