Optimization of β-D-glucuronide synthesis using UDP-glucuronyl transferase

Enzyme and Microbial Technology

Volumn 24, Issue 7, 1999, Pages 388-396

  Stevenson, David E ^a   Hubl, Ulrike ^a  

^a CALLAGHAN INNOVATION   (New Zealand)

Author keywords

D glucuronide; Analytical standard; Enzymic synthesis; Uridine 5' diphosphoglucuronyl transferase

Indexed keywords

BIOSYNTHESIS; COMPOSITION EFFECTS; ENZYMES; PURIFICATION; SILICA GEL; SOLUBILITY; SUBSTRATES;

GLUCURONIDE;

METABOLITES;

GLUCURONOSYLTRANSFERASE;

ARTICLE; CONTROLLED STUDY; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; TECHNIQUE;

EID: 0345003995     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(98)00137-9     Document Type: Article

References (17)

1. Gibson, G. G. and Skett, P. Pathways of drug metabolism (Chapter 1) and techniques and experiments illustrating drug metabolism (Chapter 8). Introduction to Drug Metabolism 2nd Ed. Blackie, Glasgow, 1994.
2. Murdter, T. E., Sperker, B., Kivisto, K. T., McClellan, M., Fritz, P., Friedel, G., Linder, A., Bosslet, K., Toomes, T., Dierkesmann, R., and Kroemer, H. K. Enhanced uptake of doxorubicin into bronchial carcinoma: β-glucuronidase mediates release of doxorubicin from a glucuronide prodrug (HMR 1826) at the tumor site. Cancer Res. 1997, 57, 2440-2445.
3. Villari, P., Ianuzzo, M., and Torre, I. An evaluation of the use of 4-methylumbelliferyl β-glucuronide in different solid media for the detection and enumeration of Escherischia coli in foods. Lett. Appl. Microbiol. 1997, 24, 286-290.
4. Lopez, V. and Lindsay, R. C. Metabolic conjugates as precursors for characterising flavour compounds in ruminant milks. J. Agric. Food Chem. 1993, 41, 446-454.
5. Stachulski, A. V. and Jenkins, G. N. The synthesis of O-glucuronides. Nat. Prod. Rep. 15, 173-185.
6. Woolf, T. F. and Chang, T. Preparation of diastereomeric β-D-glucuronides of the bronchodilator procaterol using immobilised rabbit liver microsomal enzymes. Eur. J. Drug Metab. Pharmacokin. 1989, 14, 111-116.
7. Guenthner, T. M. and Blair, N. P. In vitro synthesis of fluorescein monoglucuronide. Pharmacology 1988, 37, 341-348.
8. Jackson, C.-J. C., Hubbard, J. W., and Midha, K. K. Biosynthesis and characterisation of glucuronide metabolites of fluphenazine: 7-hydroxyfluphenazine glucuronide and fluphenazine glucuronide. Xenobiotica 1991, 21, 383-393.
9. Gygax, D., Spies, P., Winkler, T., and Pfaar, U. Enzymatic synthesis of β-D-glucuronides with in situ regeneration of uridine 5′-diphosphoglucuronic acid. Tetrahedron 1991, 47, 5119-5122.
10. Johnson, D. B., Swanson, M. J., Barker, C. W., Fanska, C. B., and Murrill, E. E. Glucuronidation of lipophilic substrates: Preparation of 3-benzo[a]pyrenyl β-D-glucopyranosiduronic acid in multimilligram quantities by microsomal UDP-glucuronyl transferase. Prep. Biochem. 1979, 9, 391-406.
11. Dulik, D. M. and Fenselau, C. Use of immobilised enzymes in drug metabolism studies. FASEB J. 1988, 2, 2235-2240.
12. Zihnioglu, F. and Telefoncu, A. Substrate specificity and the use of chitosan-entrapped rabbit hepatic microsomal UDP-glucuronyl transferase for detoxification. Art. Cells, Blood Subs. Immob. Biotechnol. 1995a, 23, 533-545.
13. Zihnioglu, F. and Telefoncu, A. Preparation and characterisation of chitosan-entrapped microsomal UDP-glucuronyl transferase. Art. Cells, Blood Subs. Immob. Biotechnol. 1995b, 23, 545-552.
14. Sigma Quality Control Test Procedure; Enzymatic Assay of Uridine-5′-diphosphoglucuronyl Transferase. Sigma Chemical Co., 1994.
15. Fenselau, C., Pallante, S., and Parikh, I. Solid-phase synthesis of drug glucuronides by immobilised glucuronyltransferase. J. Med. Chem. 1976, 19, 679-683.
16. Sigma Chemical Catalogue, 1996, p 1051.
17. Schmitt, G., Droenner, P., and Aderjan, R. Ethyl glucuronide concentration in serum of human volunteers, teetotalers and suspected drinking drivers. J. Forensic Sci. 1997, 42, 1099-1102.