Physicochemical and Enzymatic Properties of Benzyl Isothiocyanate Derivatized Proteinases

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 12, 1998, Pages 5043-5051

  Rawel, Harshadrai M ^a   Kroll, Jürgen ^a   Riese Schneider, Brigitte ^a   Haebel, Sophie ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Bromelain; Casein; Enzyme derivatization; IEF; Isothiocyanates; MALDI MS; Myoglobin; Papain; Proteolytic degradation; RP HPLC; Trypsin; chymotrypsin

Indexed keywords

EID: 0000029121     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980245j     Document Type: Article

References (30)

1. Adler-Nissen, J. Determination of the degree of hydrolysis of food protein hydrolysates by trinitrobenzenesulfonic acid. J. Agric. Food Chem. 1972, 27, 1256-1262.
2. Arnon, R. Papain. In Proteolytic Enzymes; Perlmann, G. E., Lorand, L., Eds.; Academic Press: New York, 1970; Vol. 19, pp 226-244.
3. Bennett, R. N.; Kiddle, G.; Wallsgrove, R. M. Biosynthesis of benzylglucosinolate, cyanogenic glucosides and phenylpropanoids in Carica papaya. Phytochemistry 1997, 45, 59-66.
4. Brüsewitz, G.; Cameron, B. D.; Chasseaud, L. F.; Görler, K.; Hawkins, D. R.; Koch, H.; Mennicke, W. H. The metabolism of benzylisothiocyanate and its cystein conjugate. Biochem. J. 1977, 162, 99-107.
5. Cooreman, W. M.; Scharpé, S.; Demeester, J.; Lauwers, A. Bromelain, biochemical and pharmacological properties. Pharm. Acta Helv. 1976, 51, 73-79.
6. Drobnica, L.; Gemeiner, P. Kinetics of decomposition and dissociation constants of the S-esters of N-monosubstituted dithiocarbamic acids. Collect. Czech. Chem. Commun. 1975, 40, 3346-3356.
7. Drobnica, L.; Gemeiner, P. Use of isothiocyanates as "reporter" groups in modification of enzymes. In Protein Structure and Evolution; Fox, J. L., Deyl, Z., Blazej, A., Eds.; Dekker: New York, 1976; pp 105-115.
8. Drobnica, L.; Podhradsky, D.; Gemeiner, P. Kinectics of the reactions of isothiocyanates with sulphides and thiols. Collect. Czech. Chem. Commun. 1975, 40, 3688-3697.
9. Engst, R.; Schnaak, W. Residues of dithiocarbamate fungicides and their metabolites on plant foods. Residue Rev. 1974, 52, 45-67.
10. Hayakawa, S.; Nakai, S. Relationships of hydrophobicity and net charge to the solubility of milk and soy proteins. J. Food Sci 1985, 50, 486-491.
11. Hoffmann, K. Die Funktion der Aminosäuren Cystein und Cystin des Fleisches und Methoden zur Bestimmung ihrer Sulfhydryl (SH) und Disulfid (SS)-Gruppen [Function of amino acids cysteine and cystine of meat and methods for determination of their sulfhydryl (SH) and disulfide (SS) groups]. Fleischwirtschaft 1977, 12, 2225-2237.
12. Kawakishi, S.; Kaneko, T. Interaction of protein with allyl isothiocyanate. J. Agric. Food Chem. 1987, 35, 85-88.
13. Kishore Kumar Murthy, N. V,; Narasinga Rao, M. S. Interaction of allyl isothiocyanate with mustard 12S protein, J. Agric. Food Chem. 1986, 34, 448-452.
14. Kroll, J.; Jancke, H. J. Reaktionen von Benzyl-ITC mit Glutathion: NMR-spektroskopische Untersuchungen (Reaction of benzyl-ITC with glutathione: NMR spectroscopy investigation). Nahrung 1994, 38, 96-98.
15. Kroll, J.; Rawel, H. Reactions of benzyl isothiocyanate with myoglobin. J. Sci. Food Agric. 1996, 72, 376-384.
16. Kroll, J.; Rawel, H.; Kröck, R.; Proll, J.; Schnaak, W. Interactions of isothiocyanates with egg white proteins. Nahrung 1994a, 38, 53-60.
17. Kroll, J.; Noack, J.; Rawel, H.; Kröck, R.; Proll, J. Chemical properties of benzyl isothiocyanate with egg-white protein fractions. J. Sci. Food Agric. 1994b, 65, 337-345.
18. Laemmli, U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T. Nature 1970, 277, 680-685.
19. Lehninger, A. L.; Nelson, D. L.; Cox, M. M. In Prinzipien der Biochemie; Spekrum Akademischer Verlag: Heidelberg, 1994; pp 256-257.
20. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, J. Protein measurement with Folin phenol reagent. J. Biol Chem. 1951, 193, 265-275.
21. Markwell, M. A. K.; Haas, S. M.; Bieber, L. L.; Tolbert, N. E. A modification of the Lowry procedure to simplify protein determination in membrane and lipoprotein samples. Anal. Biochem. 1978, 87, 206-210.
22. Mennicke, W. H.; Görler, K; Krumbiegel, G.; Lorenz, D.; Rittmann, N. Studies on the metabolism and excretion of benzyl isothiocyanate in man. Xenobiotika 1988, 18, 4, 441 -447.
23. Murachi, T. Bromelain enzymes. In Proteolytic Enzymes; Perlmann, G. E., Lorand, L., Eds.; Academic Press: New York, 1970; Vol. 19, pp 273-285.
24. Patrickios, C. S.; Yamasaki, E. N. Polypeptide amino acid composition and isoelectric point. II. Comparison between experiment and theory. Anal. Biochem. 1995, 231, 82-91.
25. Rawel, H.; Kroll, J. Some aspects of reactions of benzyl isothiocyanate with bovine sarcoplasmic proteins. Nahrung 1995, 39, 465-474.
26. Ritonja, A.; Rowan, A. D.; Buttle, D. J.; Rawlings, N. D.; Turk, V.; Barrett, A. J. Stem bromelain: amino acid sequence and implications for a weak binding of cystatin. FEBS Lett. 1989, 247, 419-424.
27. Rosinke, B.; Strupat, K.; Hillenkamp, F.; Rosenbusch, J.; Dencher, N.; Krüger, U.; Galla H.-J. Matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) of membrane proteins and noncovalent complexes. J. Mass Spectrom. 1995, 30, 1462-1468.
28. Tang, C.-S. Benzyl isothiocyanate as naturally occurring papain inhibitor. J. Food Sci. 1974, 39, 94-96.
29. Vestal, M. L.; Juhasz, P.; Martin, S. A. Delayed extraction matrix-assisted laser desorption time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 1995, 9, 1044-1050.
30. Walsh, K. A. Trypsinogens and trypsin of various species. In Proteolytic Enzymes; Perlmann, G. E., Lorand, L., Eds.; Academic Press: New York, 1970; Vol. 19, pp 41-63.