Peptide synthesis using proteases dissolved in organic solvents

Enzyme and Microbial Technology

Volumn 20, Issue 8, 1997, Pages 623-628

  Sergeeva, Maria V ^a   Paradkar, Vikram M ^a   Dordick, Jonathan S ^a,b  

^a University of Iowa   (United States)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

Enzymatic catalysis in organic solvents; Enzyme catalyzed peptide synthesis; Organic solvent soluble enzymes

Indexed keywords

AMINO ACIDS; CATALYSIS; ENZYME KINETICS; HYDRATION; HYDROLYSIS; ORGANIC SOLVENTS; PROTEINS;

CHYMOTRYPSIN; ENZYMATIC CATALYSIS; PEPTIDE; PROTEASES; SUBTILISIN CARLSBERG;

BIOSYNTHESIS;

ACETIC ACID ETHYL ESTER; AMIDE; AMINO ACID; CHYMOTRYPSIN A; DIPEPTIDE; ORGANIC SOLVENT; PEPTIDE; PROTEINASE; SUBTILISIN; TETRAHYDROFURAN; TRIPEPTIDE; WATER;

ARTICLE; CATALYST; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; HYDROPHILICITY; HYDROPHOBICITY; MICHAELIS CONSTANT; PEPTIDE SYNTHESIS; SOLUBILITY;

EID: 0031172115     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(96)00272-4     Document Type: Article

References (25)

1. Taylor, M. D., Amidon, G. L., eds (1995): Peptide-Based Drug Design: Controlling Transport and Metabolism, American Chemical Society, Washington, DC
2. Berson, S. A., Yalow, R. S. (1973): Peptide Hormones, American Elsevier Pub. Co., New York
3. Duke, S. D., Abbas, H. K. Natural products with potential use as herbicides. ACS Symp Ser 1995, 582, 348-362
4. Guinn, R. M., Margot, A. O., Taylor, J. R., Schumacher, M., Clark, D. S., Blanch, H. W. Synthesis and characterization of polyamides containing unnatural amino-acids. Biopolymers 1995, 35, 503-512
5. Merrifield, R. B. Solid phase peptide synthesis in the synthesis of a tetrapeptide. J Am Chem Soc. 1963, 85, 2149-2154
6. Desai, M. C., Zuckermann, R. N., Moos, W. H. Recent advances in the generation of chemical diversity libraries. Drug Dev. Res. 1994, 33, 174-188
7. Pinilla, C., Appel, J., Blondelle, S., Dooley, C., Dorner, B., Eichler, J., Ostresh, J., Houghten, R. A. A review of the utility of soluble peptide combinatorial libraries. Biopolymers 1995, 37, 221-240
8. Homandberg, G. A., Mattis, J. A., Laskowski, M. Synthesis of peptide bond by proteases. Addition of organic cosolvents shifts peptide bond equillibria towards synthesis. Biochemistry 1978, 17, 5220-5227
9. Kimura, Y., Tari, Y., Adachi, S., Matsuno, R. Enzymatic synthesis of peptides with hydrophilic amino acids in water-miscible organic solvent. Ann N Y Acad Sci (Enzyme Eng. XI, D. S. Clark, D. A. Estell, eds.) 1992, 672, 458-461
10. Deschrevel, B., Vincent, J. C., Threllier, M. Kinetic study of the α-chymotrypsin-catalyzed hydrolysis and synthesis of peptide bond in a monophasic aqueous/organic reaction medium. Arch Biochem Biophys. 1993, 304, 45-52
11. Aldercreutz P., Clapes, P. Catalytic properties of α-chymotrypsin in organic media. Biomed Biochim Acta 1991, 50, S 55-S 60
12. Bemquerer, M. P., Adlercreutz, P., Tominaga, M. Pepsin-catalyzed peptide synthesis in organic media: Studies with free and immobilized enzyme. Int J Pept Prot Res 1994, 44, 5, 448-456
13. Hwang, K. A., Lee, S. B., Lee, K. H. Effect of water activity on thermolysin-catalyzed peptide synthesis in organic solvents. Biotech Lett. 1995, 17, 71-76
14. Paradkar V. M., Dordick, J. S. Mechanism of extraction of chymotrypsin into isooctane at very low concentration of Aerosol OT in the absence of reversed micelles. Biotechnol Bioeng. 1994, 43, 529-540
15. Paradkar, V. M., Dordick, J. S. Aqueous-like activity of α-chymotrypsin dissolved in nearly anhydrous organic solvents. J Am Chem Soc. 1994, 116, 5009-5010
16. Wangikar, P. P., Graycar, T. P., Estell, D. A., Clark, D. S., Dordick, J. S. Protein and solvent engineering of subtilisin BPN' in nearly anhydrous organic media. J Amer Chem Soc. 1993, 115, 12231-12237
17. Halling, P. J. Effect of thermodynamic water activity on protease-catalyzed peptide synthesis in mainly organic media. Biomed Biochim Acta 1991, 50, S61-S66
18. Bone, S., Pethig, R. Dielectric studies of protein hydration and hydration-induced flexibility. J Mol Biol. 1985, 181, 323-326
19. Affleck, R., Xu, Z.-F., Suzawa, V., Focht, K., Clark, D. S., Dordick, J. S. Enzymatic catalysis and dynamics in low-water environments. Proc Natl Acad Sci USA 1992, 89, 1100-1104
20. Wangikar, P. P., Rich, J. O., Clark, D. S., Dordick, J. S. Probing enzymatic transition-state hydrophobicities. Biochemistry 1995, 34, 12302-12310
21. Dorovska, V. N., Varfolomeyev, S.D., Kazanskaya, N. F., Klyosov, A. A., Martinek, K. The influence of the geometric properties of the active center on the specificity of α-chymotrypsin catalysis. FEBS Letters, 1972, 23, 122-124
22. 3 space. Arch Biochem Biophys. 1979, 194, 542-551
23. Ricca, J. M., and Crout, D. H. G. Peptide synthesis catalyzed by chymotrypsin in organic solvents. J Chem Soc Perkin Trans, 1. 1989, 11, 2126-2128
24. Nagashima, T., Watanabe, A., Kise, H. Peptide synthesis by proteases in organic solvents: Medium effect on substrate specificity. Enzyme Microb Technol. 1992, 14, 842-846
25. Cerovsky, V. Serine proteinase-catalyzed incorporation of D-amino acids into model peptides in acetonitrile with low water content. Biomed Biochim Acta 1991, 50, S44-S49