Transglutaminase-catalyzed synthesis of trypsin-cyclodextrin conjugates: Kinetics and stability properties

Biotechnology and Bioengineering

Volumn 81, Issue 6, 2003, Pages 732-737

  Villalonga, Reynaldo ^a   Fernández, Michael ^a   Fragoso, Alex ^b   Cao, Roberto ^b   Di Pierro, Prospero ^c   Mariniello, Loredana ^c   Porta, Raffaele ^c  

^a UNIVERSITY OF MATANZAS   (Cuba)

^b UNIVERSITY OF HAVANA   (Cuba)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Cyclodextrin; Enzyme stability; Modified enzyme; Transglutaminase; Trypsin

Indexed keywords

CATALYST ACTIVITY; CHEMICAL MODIFICATION; PH EFFECTS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AUTOLYTIC DEGRADATION;

ENZYME KINETICS;

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN; GAMMA CYCLODEXTRIN; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE; TRYPSIN;

ALKALINITY; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONJUGATE; ENZYME KINETICS; ENZYME STABILITY; NONHUMAN; PROTEIN DEGRADATION; PROTEIN MODIFICATION; PROTEIN SYNTHESIS; TEMPERATURE DEPENDENCE; THERMOSTABILITY;

ANIMALS; ARGININE; CATALYSIS; CATTLE; COENZYMES; ENZYME ACTIVATION; ENZYME STABILITY; GLUCOSYLTRANSFERASES; HEAT; KINETICS; MACROMOLECULAR SUBSTANCES; MULTIENZYME COMPLEXES; PROTONS; SUBSTRATE SPECIFICITY; TRANSGLUTAMINASES; TRYPSIN;

BOVINAE;

EID: 0037457385     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/bit.10520     Document Type: Article

References (41)

1. Aeschlimann D, Paulsson M. 1994. Transglutaminases: Protein crosslinking enzymes in tissues and body fluids. Thromb Haemost 71: 402-415.
2. Bechtold U, Otterbach JT, Pasternack R, Fuchsbauer HL. 2000. Enzymic preparation of protein G-peroxidase conjugates catalysed by transglutaminase. J Biochem 127:239-245.
3. Bruneel D, Schacht E. 1993. Chemical modification of pullulan: 1. Peroxidate oxidation. Polymer 34:2628-2632.
4. Darias R, Villalonga R. 2001. Functional stabilization of cellulase by covalent modification with chitosan. J Chem Technol Biotechnol 76: 489-493.
5. Dubois MK, Gilles A, Hamilton JK, Rebers PA, Smith F. 1956. Colorimetric method for determination of sugars and related substances. Anal Chem 28:350-356.
6. Esposito C, Costa C, Amoresano A, Mariniello L, Sommella MG, Caputo I, Porta R. 1999. Transglutaminase-mediated amine incorporation into substance P protects the peptide against proteolysis in vitro. Regul Pept 84:75-80.
7. 5) spermidine derivative of substance P. J Neurochem 65:420-426.
8. Folk JE, Chung SI. 1985. Transglutaminases. Meth Enzymol 113:358-364.
9. Fragoso A, Cao R, Villalonga R. 1995. Superoxide dismutase mimetic activity of the metal (II) complexes of a dithiocarbamate derivative of β-cyclodextrin. J Carbohydr Chem 14:1389-1396.
10. Gómez L, Villalonga R. 2000. Functional stabilization of invertase by covalent modification with pectin. Biotechnol Lett 22:1191-1195.
11. Griebenow K, Díaz-Laureano Y, Montañez-Clemente I, Rodríguez L, Vidal MW, Barietta G. 1999. Improved enzyme activity and enantioselectivity in organic solvents by methyl-β-cyclodextrin. J Am Chem Soc 121:8157-8163.
12. Josten A, Meusel M, Spener F. 1998. Microbial transglutaminase-mediated synthesis of hapten-protein conjugates for immunoassays. Anal Biochem 258:202-208.
13. Kazan D, Erarslan A. 1997. Stabilization of Escherichia coli penicillin G acylase by polyethylene glycol against thermal inactivation. Appl Biochem Biotechnol 62:1-13.
14. Klibanov AM. 1979. Enzyme stabilization by immobilization. Anal Biochem 93:1-25.
15. Krieger M, Kay LM, Stroud RM. 1974. Structure and specific binding of trypsin: Comparison of inhibited derivatives and a model for substrate binding. J Mol Biol 83:209-230.
16. Laemmli UK. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685.
17. R of poly(ethylene glycol) and the stability of horseradish peroxidase-poly(ethylene glycol) adducts under various denaturing conditions. Biotechnol Appl Biochem 20:397-413.
18. Laskowski M. 1955. Trypsinogen and trypsin. Meth Enzymol 2:26-36.
19. Lowry OH, Rosebrough NJ, Farr AL, Randall R. 1951. Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
20. Mancuso F, Calignano A, Cozzolino A, Metafora S, Porta R. 1996. Inhibition of zymosan-induced air-pouch inflammation by rat seminal vesicle protein and by its spermidine derivative. Eur J Pharmacol 312:327-332.
21. 5) spermidine derivative of substance P is a selective tool for neurokinin-2 receptors characterization. Peptides 19:683-690.
22. Mancuso F, Porta R, Calignano A, Di Pierro P, Sommella MC, Esposito C. 2001. Substance P and its transglutaminase-synthesized derivatives elicit yawning behavior via nitric oxide in rats. Peptides 22:1453-1457.
23. Metafora S, Peluso G, Persico P, Ravagnan G, Esposito C, Porta R. 1989. Immunosuppressive and anti-inflammatory properties of a major protein secreted from the epithelium of the rat seminal vesicles. Biochem Pharmacol 38:121-131.
24. Minagawa H, Kaneko H. 2000. Effect of double mutation on thermostability of lactate oxidase. Biotechnol Lett 22:1131-1133.
25. Mozhaev VV, Šikšnis VA, Melik-Nubarov NS, Galkantaite NZ, Denis GJ, Butkus EP, Zaslavsky BY, Mestechkina NM, Martinek K. 1988. Protein stabilization via hydrophilization. Covalent modification of trypsin and α-chymotrypsin. Eur J Biochem 173:147-154.
26. Murphy A, Ó Fágáin C. 1996. Stability characteristics of chemicallymodified trypsin. J Biotechnol 49:163-171.
27. Perona JJ, Craik CS. 1995. Structural basis of substrate specificity in the serine proteases. Prot Sci 4:337-360.
28. Persico P, Calignano A, Mancuso F, Marino G, Pucci P, Esposito C, Mariniello L, Porta R. 1992. Substance P inactivation by transglutaminase in vitro. Peptides 13:151-154.
29. Porta R, Esposito C, Gentile V, Mariniello L, Peluso G, Metafora S. 1990. Transglutaminase-catalyzed modifications of SV-IV, a major protein secreted from the rat seminal vesicle epithelium. Int J Peptide Prot Res 35:117-122.
30. Privalov PL, Gill SJ. 1988. Stability of protein structure and hydrophobic interaction. Adv Prot Chem 39:191-234.
31. Saito T, Kawashima K, Lina KH, Inagaki H, Maeda S, Yoshida Y, Kobayashi T. 1997. Influence of aldehyde groups on the thermostability of an immobilized enzyme on an inorganic support. Mater Sci Eng C 5:149-152.
32. Schwert GB, Takenaka Y. 1955. A spectrophotometric determination of trypsin and chymotrypsin. Biochim Biophys Acta 16:570-575.
33. Sunna A, Puls J, Antranikian G. 1997. Characterization of the xylanolytic enzyme system of the extreme thermophilic anaerobic bacteria Thermotoga maritima, T. neapolitana, and T. thermarum. Compr Biochem Phys A 118:453-461.
34. Szejtli J. 1982. Cyclodextrins and their inclusion compounds. Budapest: Akadémiai Kiadó.
35. Szejtli J. 1998. Introduction and general overview of cyclodextrins. Chem Rev 98:1743-1754.
36. Tufano MA, Porta R, Farzati B, Di Pierro P, Rossano F, Catalanotti P, Baroni A, Metafora S. 1996. Rat seminal vesicle protein SV-IV and its transglutaminase-synthesized polyaminated derivative SPD2-SV-IV induce cytokine release from human resting lymphocytes and monocytes in vitro. Cel Immunol 168:148-157.
37. Venkatesh R, Sundaram PV. 1998. Modulation of stability properties of bovine trypsin after in vitro structural changes with a variety of chemical modifiers. Prot Eng 11:691-698.
38. Villalonga R, Gómez L, Ramírez HL, Villalonga ML. 1999. Stabilization of α-amylase by chemical modification with carboxymethylcellulose. J Chem Technol Biotechnol 7:635-638.
39. Villalonga R, Villalonga ML, Gómez L. 2000. Preparation and functional properties of trypsin modified by carboxymethylcellulose. J Mol Catal B Enzym 10:483-490.
40. Walsh KA. 1970. Trypsinogen and trypsin of various species. Meth Enzymol 19:41-63.
41. Zhong N, Byun HS, Bittman, R. 1998. A convenient method for the monotosylation of β-cyclodextrin on the primary side. Tetrahed Lett 38: 2919-2920.