Highly regioselective glucosylation of 2'-deoxynucleosides by using the crude β-glycosidase from bovine liver

Journal of Biotechnology

Volumn 155, Issue 2, 2011, Pages 203-208

  Ye, Min ^a   Yu, Chun Yang ^a   Li, Ning ^a   Zong, Min Hua ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Glycosidase; Bovine liver; Disaccharide nucleosides; Glucosylation; Regioselectivity

Indexed keywords

ACTIVE COMPONENTS; BOVINE LIVER; BUFFER PH; CRUDE ENZYMES; DEOXYNUCLEOSIDES; DEOXYURIDINE; DISACCHARIDE NUCLEOSIDES; ENZYMATIC REACTION; ENZYME DOSAGE; GLUCOSYLATION; GLYCOSIDASES; KEY FACTORS; MODEL REACTIONS; ORGANIC LABORATORY; REGIO-SELECTIVE;

ENZYMES; REGIOSELECTIVITY;

GLYCOSYLATION;

2' DEOXYNUCLEOSIDE; BETA GLYCOSIDASE; DEOXYURIDINE DERIVATIVE; GLYCOSIDASE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COW; ENZYME ACTIVITY; GLYCOSYLATION; LIVER; NONHUMAN; PH; PRIORITY JOURNAL; TEMPERATURE;

ANIMALS; BETA-GLUCOSIDASE; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DISACCHARIDES; GLYCOSYLATION; HYDROGEN-ION CONCENTRATION; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEOSIDES; TEMPERATURE;

BOVINAE;

EID: 80051475256     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2011.06.031     Document Type: Article

References (29)

1. Abraham R., Aman N., von Borstel R., Darsley M., Kamireddy B., Kenten J., Morris G., Titmas R. Conjugates of COL-1 monoclonal antibody and β-d-galactosidase can specifically kill tumor cells by generation of 5-fluorouridine from the prodrug β-d-galactosyl-5-fluorouridine. Cell Biochem. Biophys. 1994, 24:127-133.
2. Andreotti G., Trincone A., Giordano A. Convenient synthesis of β-galactosyl nucleosides using the marine β-galactosidase from Aplysia fasciata. J. Mol. Catal. B: Enzym. 2007, 47:28-32.
3. Battaglia G., La Russa M., Bruno V., Arenare L., Ippolito R., Copani A., Bonina F., Nicoletti F. Systemically administered d-glucose conjugates of 7-chlorokynurenic acid are centrally available and exert anticonvulsant activity in rodents. Brain Res. 2000, 860:149-156.
4. Binder W.H., Kahlig H., Schmid W. Galactosylation by use of β-galactosidase: enzymatic syntheses of disaccharide nucleosides. Tetrahedron: Asymmetry 1995, 6:1703-1710.
5. De Clercq E. Antiviral drugs in current clinical use. J. Clin. Virol. 2004, 30:115-133.
6. De Clercq E., Field H.J. Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br. J. Pharmacol. 2006, 147:1-11.
7. Diaz-Rodriguez A., Fernandez S., Lavandera I., Ferrero M., Gotor V. Novel and efficient regioselective enzymatic approach to 3'-, 5'- and 3',5'-di-O-crotonyl 2'-deoxynucleoside derivatives. Tetrahedron Lett. 2005, 46:5835-5838.
8. Dwevedi A., Kayastha A.M. Stabilization of β-galactosidase (from peas) by immobilization onto Amberlite MB-150 beads and its application in lactose hydrolysis. J. Agric. Food Chem. 2009, 57:682-688.
9. Efimtseva E.V., Kulikova I.V., Mikhailov S.N. Disaccharide nucleosides as an important group of natural compounds. Mol. Biol. 2009, 43:301-312.
10. Efimtseva E.V., Mikhailov S.N. Disaccharide nucleosides and oligonucleotides on their basis. New tools for the study of enzymes of nucleic acid metabolism. Biochemistry (Moscow) 2002, 67:1136-1144.
11. Efimtseva E.V., Mikhailov S.N. Disaccharide nucleosides. Russ. Chem. Rev. 2004, 73:401-414.
12. Ferrero M., Gotor V. Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem. Rev. 2000, 100:4319-4347.
13. Gekas V., Lopez-Leiva M. Hydrolysis of lactose: a literature review. Process Biochem. 1985, 20:2-12.
14. Hirata T., Koya K., Sarfo K.J., Shimoda K., Ito D.I., Izumi S., Ohta S., Lee Y.S. Glucosylation of benzyl alcohols by the cultured suspension cells of Nicotiana tabacum and Catharanthus roseus. J. Mol. Catal. B: Enzym. 1999, 6:67-73.
15. Joo A.-R., Jeya M., Lee K.-M., Sim W.-I., Kim J.-S., Kim I.-W., Kim Y.-S., Oh D.-K., Gunasekaran P., Lee J.-K. Purification and characterization of a β-1,4-glucosidase from a newly isolated strain of Fomitopsis pinicola. Appl. Microbiol. Biotechnol. 2009, 83:285-294.
16. Kemeny N., Huang Y., Cohen A.M., Shi W., Conti J.A., Brennan M.F., Bertino J.R., Turnbull A.D., Sullivan D., Stockman J., Blumgart L.H., Fong Y. Hepatic arterial infusion of chemotherapy after resection of hepatic metastases from colorectal cancer. N. Engl. J. Med. 1999, 341:2039-2048.
17. Landowski C.P., Song X.Q., Lorenzi P.L., Hilfinger J.M., Amidon G.L. Floxuridine amino acid ester prodrugs: enhancing Caco-2 permeability and resistance to glycosidic bond metabolism. Pharm. Res. 2005, 22:1510-1518.
18. Li N., Smith T.J., Zong M.H. Biocatalytic transformation of nucleoside derivatives. Biotechnol. Adv. 2010, 28:348-366.
19. Li N., Zong M.H., Ma D. Regioselective acylation of nucleosides catalyzed by Candida antarctica lipase B: enzyme substrate recognition. Eur. J. Org. Chem. 2008, 537:5-5378.
20. Li N., Zong M.H., Ma D. Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition. Tetrahedron 2009, 65:1063-1068.
21. Li N., Zong M.H., Ma D. Thermomyces lanuginosus lipase-catalyzed regioselective acylation of nucleosides: enzyme substrate recognition. J. Biotechnol. 2009, 140:250-253.
22. 13C NMR. Tetrahedron Lett. 1981, 22:4401-4404.
23. Mizuma T., Ohta K., Hayashi M., Awazu S. Intestinal active absorption of sugar-conjugated compounds by glucose transport system: implication of improvement of poorly absorbable drugs. Biochem. Pharmacol. 1992, 43:2037-2039.
24. O'Connell S., Walsh G. A novel acid-stable, acid-active β-galactosidase potentially suited to the alleviation of lactose intolerance. Appl. Microbiol. Biotechnol. 2010, 86:517-524.
25. Sanghvi Y.S., Cook P.D. Nucleosides and Nucleotides as Antitumor and Antiviral Agents 1993, Plenum, New York.
26. Tipton K.F., Dixon H.B.F. Effects of pH on Enzymes 1979, Academic Press.
27. Yoo C.B., Jones P.A. Epigenetic therapy of cancer: past, present and future. Nat. Rev. Drug Discov. 2006, 5:37-50.
28. Yu H.L., Xu J.H., Lu W.Y., Lin G.Q. Identification, purification and characterization of β-glucosidase from apple seed as a novel catalyst for synthesis of O-glucosides. Enzyme Microb. Technol. 2007, 40:354-361.
29. Zeng Q.M., Li N., Zong M.H. Highly regioselective galactosylation of floxuridine catalyzed by β-galactosidase from bovine liver. Biotechnol. Lett. 2010, 32:1251-1254.