β-Glycosylamidine as a ligand for affinity chromatography tailored to the glycon substrate specificity of β-glycosidases

Carbohydrate Research

Volumn 338, Issue 14, 2003, Pages 1477-1490

  Inoue, Kazuko ^a   Hiratake, Jun ^a   Mizutani, Masaharu ^a   Takada, Masayasu ^b   Yamamoto, Mikio ^b   Sakata, Kanzo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Fuji   (Japan)

Author keywords

Affinity chromatography; Affinity ligand; Glycon substrate specificity; Penicillium multicolor galactosidase; Tea leaf glucosidase; Glycosylamidine

Indexed keywords

ADSORBENTS; AFFINITY CHROMATOGRAPHY; ENZYME IMMOBILIZATION; PURIFICATION; SODIUM CHLORIDE; SYNTHESIS (CHEMICAL);

SPACERS;

CARBOHYDRATES;

2 IMINOTHIOLANE; AMIDINE; AMINOSUGAR; BETA GALACTOSYLAMIDINE; BETA GLYCOSYLAMIDINE; GLYCOSIDASE; GLYCOSIDASE INHIBITOR; LIGAND; MALEIMIDE DERIVATIVE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; ENZYME BINDING; ENZYME SPECIFICITY; ENZYME SUBSTRATE; NONHUMAN; PENICILLIUM; PENICILLIUM MULTICOLOR; PRIORITY JOURNAL; TEA;

CAMELLIA; CAMELLIA SINENSIS; PENICILLIUM;

EID: 0037757544     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00201-5     Document Type: Article

References (46)

1. Dwek R.A. Chem. Rev. 96:1996;683-720.
2. Kornfeld R., Kornfeld S. Annu. Rev. Biochem. 54:1985;631-664.
3. Henrissat B. Biochem. J. 280:1991;309-316.
4. Henrissat B., Davies G. Curr. Opin. Struct. Biol. 7:1997;637-644.
5. Wilchek M., Miron T., Kohn J. Methods Enzymol. 104:1984;3-55.
6. Barker R., Chiang C.-K., Trayer I.P., Hill R.L. Methods Enzymol. 34:1974;317-328.
7. Giudicelli J., Emiliozzi R., Vannier C., De Burlet G., Sudaka P. Biochim. Biophys. Acta. 612:1980;85-96.
8. Grabowski G.A., Dagan A. Anal. Biochem. 141:1984;267-279.
9. Hiraizumi S., Spohr U., Spiro R.G. J. Biol. Chem. 269:1994;4697-4700.
10. Sangseethong K., Penner M.H. Carbohydr. Res. 314:1998;245-250.
11. Mega T., Matsushima Y. J. Biochem. 79:1976;185-194.
12. Jain R.S., Binder R.L., Levy-Benshimol A., Buck C.A., Warren L. J. Chromatogr. 139:1977;283-290.
13. Piyachomkwan K., Gable K.P., Penner M.H. Carbohydr. Res. 303:1997;255-259.
14. Abo S., Ciccotosto S., Alafaci A., von Itzstein M. Carbohydr. Res. 322:1999;201-208.
15. Watanabe T., Sato T., Yoshioka S., Koshijima T., Kuwahara M. Eur. J. Biochem. 209:1992;651-659.
16. Harpaz N., Flowers H.M., Sharon N. Biochim. Biophys. Acta. 341:1974;213-221.
17. Harpaz N., Flowers H.M. Methods Enzymol. 34:1974;347-350.
18. Harpaz N., Flowers H.M., Sharon N. Eur. J. Biochem. 77:1977;419-426.
19. Bishop D.F., Desnick R.J. J. Biol. Chem. 256:1981;1307-1316.
20. Presper K.A., Concha-Slebe I., De T., Basu S. Cabohydr. Res. 155:1986;73-87.
21. Hettkamp H., Legler G., Bause E. Eur. J. Biochem. 142:1984;85-90.
22. Kang M.S., Liu P.S., Bernotas R.C., Harry B.S., Sunkara P.S. Glycobiology. 5:1995;147-152.
23. Legler G., Bieberich E. Arch. Biochem. Biophys. 260:1988;427-436.
24. Matern H., Heinemann H., Legler G., Matern S. J. Biol. Chem. 272:1997;11261-11267.
25. Bause E., Gross A., Schweden J. FEBS Lett. 278:1991;167-170.
26. Schweden J., Bause E. Biochem. J. 264:1989;347-355.
27. Scudder P., Neville D.C.A., Butters T.D., Fleet G.W., Dwek R.A., Rademacher T.W., Jacob G.S. J. Biol. Chem. 265:1990;16472-16477.
28. Guo W., Hiratake J., Ogawa K., Yamamoto M., Ma S.-J., Sakata K. Bioorg. Med. Chem. Lett. 11:2001;467-470.
29. Isbell H.S., Frush H.L. J. Org. Chem. 23:1958;1309-1319.
30. Morrison J.F., Walsh C.T. Adv. Enzymol. Rel. Areas Mol. Biol. 61:1988;201-301.
31. Schloss J.V. Acc. Chem. Res. 21:1988;348-353.
32. Bülow A., Plesner I.W., Bols M. Biochim. Biophys. Acta. 1545:2001;207-215.
33. Cuatrecasas P., Anfinsen C.B. Ann. Rev. Biochem. 40:1971;259-278.
34. Steers E. Jr., Cuatrecasas P. Methods Enzymol. 34:1974;350-358.
35. Ijima Y., Ogawa K., Watanabe N., Usui T., Ohnishi-Kameyama M., Nagata T., Sakata K. J. Agric. Food Chem. 46:1998;1712-1718.
36. Manger I.D., Rademacher T.W., Dwek R.A. Biochemistry. 31:1992;10724-10732.
37. Dale M.P., Ensley H.E., Kern K., Sastry K.A.R., Byers L.D. Biochemistry. 24:1985;3530-3539.
38. He S., Withers S.G. J. Biol. Chem. 272:1997;24864-24867.
39. Esen, A. β-Glucosidases: Overview; Conn, E.E. β-Glucosidases in Plants: Substrate Specificity. In: Esen, A. (Ed.) β-Glucosidases. Biochemistry and Molecular Biology, ACS Symposium series 533: ACS, Washington, DC, 1994; pp. 1-14 and 15-26.
40. Czjzek M., Cicek M., Zamboni V., Bevan D.R., Henrissat B., Esen A. Proc. Natl. Acad. Sci. USA. 97:2000;13555-13560.
41. Unno T., Ide K., Yazaki T., Tanaka Y., Nakakuki T., Okada G. Biosci. Biotech. Biochem. 57:1993;2172-2173.
42. Narayanan S.R. J. Chromatogr. A. 658:1994;237-258.
43. Rich D.H., Gesellchen P.D., Tong A., Cheung A., Buckner C.K. J. Med. Chem. 18:1975;1004-1010.
44. Bradford M.M. Anal. Biochem. 72:1976;248-254.
45. Laemilli U.K. Nature. 227:1970;680-685.
46. Merril C.R., Dunan M.L., Godman D. Anal. Biochem. 110:1981;201-207.