Abstract
The study of glucuronidation reactions began 100 years ago with the isolation of a conjugate of o-nitrotoluene from the urine of dogs. Acid hydrolysis of this conjugate yielded an acidic sugar as one of the products. An identical sugar was obtained on acid hydrolysis of a conjugate of chloral hydrate exreted in human urine. The formula of the reducing sugar was given correctly as
by Schmiedeberg and Meyer in 1879 (Smith and Williams, 1970). A wide variety of organic compounds are now known to be conjugated with glucuronic acid. Predominant among these are aromatic molecules containing phenolic and carboxylic groups which form O-ether and O-ester glucuronides, respectively. Several aromatic thiols are glucuronidated, and N-glucuronides also have been reported (Dutton, 1966). The donor of the glucuronic acid moiety in these reactions was identified as UDP-glucuronic acid (Dutton and Storey, 1953; Dutton, 1966).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Arias, I. M., Wolfson, S., and Johnson, L., 1960, Studies of extrahepatic glururonide formation in normal and Gunn rats, Clin. Res. 8:28.
Arion, W. J., Wallin, B. K., Carlson, P. W., and Lange, A. J., 1972, The specificity of glucose-6-phosphatase of intact liver microsomes, J. Biol. Chem. 247:2558.
Attwood, D., Graham, A. B., and Wood, G. C., 1971, The phospholipid dependence of uridine diphosphate glucuronyltransferase, Biochem. J. 123:875.
Berry, C., and Hallinan, T., 1974, “Coupled trarisglucuronidation”: A new tool for studying the latency of UDP-glucuronyltransferase, FEBS Lett. 42:73.
Bock, K. W., and White, I. N. H., 1974, UDP-glucuronyltransferase in perfused rat liver and in microsomes: Influence of phenobarbital and 3-methylcholanthrene, Eur. J. Biochem. 46:451.
Bock, K. W., Fröhling, W., Remmer, H., and Rexer, B., 1973, Effects of phenobarbital and 3-methyl- cholanthrene on substrate specificity of rat liver microsomal UDP-gluronyltransferase, Biochim.Biophys. Acta 347:46.
Brodie, B. B., and Maickel, R. P., 1962, Comparative biochemistry of drug metabolism, in: Proceedings of the 1st International Pharmacology Meeting, Stockholm (B. B. Brodie, E. G. Endor, R. P. Maickel, and P. Lindgren, eds.), pp. 299–309. Pergamon Press, Oxford.
Cleland, W. W., 1970, Steady state kinetics, in: The Enzymes, Vol. II (P. Boyer, ed.), pp. 1–66, Academic Press, New York.
Dehlinger, P. J., Jost, P. C., and Griffith, O. H., 1974, Lipid binding to the amphipatic membrane protein cytochrome b 5, Proc. Natl. Acad. Sci. U.S.A. 71:2280.
Drucker, W. D., 1968, Glucuronic acid conjugation of tetrahydrocortisone and p-nitrophenol in the homozygous Gunn rat, Proc. Soc. Exp. Biol. Med. 129:308.
Dutton, G. J., 1966, The biosynthesis of glucuronides, in: Glucuronic Acid Free and Combined (G. J. Dutton, ed.), pp. 186–299, Academic Press, New York.
Dutton, G. J., and Greig, C. G., 1957, Observations on the distribution of glucuronide synthesis in tissues, Biochem. J. 66:52P.
Dutton, G. J., and Storey, I. D. E., 1953, The isolation of a compound of uridine diphosphate and glucuronic acid from liver, Biochem. J. 53:37.
Dutton, G. J., Langelaan, D. E., and Ross, P. E., 1964, High glucuronide synthesis in newborn liver: Choice of species and substrate, Biochem. J. 93:4P.
Eletr, S., Zakim, D., and Vessey, D. A., 1973, A spin label study of the role of phospholipids in the regulation of membrane-bound microsomal enzymes, J. Mol. Biol. 78:351.
Goldman, R., Kedem, O., and Katchalski, E., 1968, Papain-collodion membranes. II. Analysis of the kinetic behavior of enzymes immobilized in artificial membranes, Biochemistry 7:4518.
Graham, A. B., and Wood, G. C., 1969, The phospholipid dependence of UDP-glucuronyltransferase, Biochem. Biophys. Res. Commun. 37:567.
Graham, A. B., and Wood, G. C., 1973, Factors affecting the response of microsomal UDP-glucuronyltransferase to membrane perturbants, Biochim. Biophys. Acta 311:45.
Graham, A. B., Woodcock, B. G., and Wood, G. C., 1974, The phospholipid dependence of uridine diphosphate glucuronyltransferase, Biochem. J. 137:567.
Green, F. A., 1972, Erythrocyte membrane lipids and Rh antigen activity, J. Biol. Chem. 247:881.
Hänninen, O., and Puukka, R., 1970, Effect of digitonin on UDP-glucuronyltransferase in microsomal membranes, Suo. Kemistil. 43:451.
Hänninen, O., and Puukka, R., 1971, Activation of microsomal UDP-glucuronyltransferases by phospholipases, Chem. Biol. Interact. 3:282.
Hubbell, W. L., and McConnell, H. M., 1969, Orientation and motion of emphipathic spin labels in membranes, Proc. Natl. Acad. Sci. U.S.A. 64:20.
Hubbell, W. L., and McConnell, H. M., 1971, Molecular motion in spin-labelled phospholipids and membranes, J. Am. Chem. Soc. 93:314.
Isselbacher, K.J., Chrabas, M. F., and Quinn, R. C., 1962, The solubilization and partial purification of a glucuronyltransferase from rabbit liver microsomes, J. Biol. Chem. 237:3033.
Keppler, D. O. R., Rudiger, J. E. M., Bischoff, E., and Decker, K. F. A., 1970, The trapping of uridine phosphates by D-galactosamine, D-glucosamine, and 2-deoxy-D-galactose. A study on the mechanism of galactosamine hepatitis, Eur. J. Biochem. 17:246.
Kornberg, R. D., and McConnell, H. M., 1971, Lateral diffusion of phospholipids in a vessicle membrane, Proc. Natl. Acad. Sci. U.S.A. 68:2564.
Koshland, D. E., 1970, The molecular basis for enzyme regulation in:The Enzymes, Vol. I (P. Boyer, ed.), pp. 342–396, Academic Press, New York.
Lucier, G. W., McDaniel, O. S., and Mathews, H. B., 1971, Microsomal rat liver UDP-glucuronyltransferase: Effects of piperonyl butoxide and other factors on enzyme activity, Arch. Biochem Biophys. 145:520.
Lueders, K. K., and Kuff, E. C., 1967, Spontaneous and detergent activation of a glucuronyltransferase in vitro, Arch. Biochem. Biophys. 120:198.
Masotti, L., Lenaz, G., Spisni, A., and Urry, D. W., 1974, Effect of phospholipids on the protein conformation in the inner mitochondrial membranes, Biochem. Biophys. Res. Commun. 56:892.
McGonnell, H. M., Devaux, P., and Scandella, C., 1972, Lateral diffusion and phase separations in biological membranes, in: Membrane Research (C. F. Fox, ed.), pp. 27–37, Academic Press, New York.
Melhorn, R. J., and Keith, A. D., 1972, Spin labeling of biological membranes, in:Membrane Molecular Biology (C. F. Fox and A. D. Keith, eds.), p. 192, Sinauer Associates, Stamford, Connecticut.
Mowat, A. P., and Arias, I. H., 1970, Partial purification of hepatic glucuronyltransferase. Studies of some of its properties, Biochim. Biophys. Acta 212:65.
Mulder, G. J., 1971, The heterogeneity of uridine diphosphate glucuronyltransferase from rat liver, Biochem. J. 125:9.
Mulder, G. J., 1974, Heterogeneity of hepatic microsomal uridine diphosphate glucuronyltransferase: A critical evaluation, Biochem. Soc. Trans., in press.
Mulder, G. J., and Hagedoorn, A. H., 1974, UDP-glucuronyltransferase and phenolsulfotransferase in vivo and in vitro. Conjugation of harmol and harmalol, Biochem. Pharmacol. 28:2101.
Nakata, D., Zakim, D., and Vessey, D. A., 1975, Modification of protein-lipid interactions in the Gunn rat, Biochem. Pharmacol., in press.
Phillips, M. C., Ladbrooke, B. D., and Chapman, D., 1970, Molecular interactions in mixed lecithin systems, Biochim. Biophys. Acta 196:35.
Pogell, B. M., and Leloir, L. F., 1961, Nucleotide activation of liver microsomal glucuronidation, J.Biol.Chem. 236:293.
Puukka, R., and Hänninen, O., 1972, Effect of fatty acids on UDP-glucuronyltransferase activity in the rat liver microsomes, Int. J. Biochem. 3:357.
Schmid, R., 1972, Hyperbilirubinemia in: The Metabolic Basis of Inherited Disease (J. B. Stanbury, J. B. Wyngaarden, and D. S. Fredrickson, eds.), pp. 1141–1178, McGraw-Hill, New York.
Seelig, J., and Hasselbach, W., 1971, A spin label study of sarcoplasmic vesicles, Eur. J. Biochem. 21:17.
Shimshick, E. J., and McConnell, H. M., 1973, Lateral phase separation in phospholipid membranes, Biochemistry 12:2351.
Singer, S. J., and Nicolson, G. L., 1972, The fluid mosaic model of the structure of cell membranes, Science 175:720.
Smith, R. L., and Williams, R. T., 1970, History of the discovery of the conjugation mechanisms, in: Metabolic Conjugation and Metabolic and Metabolic Hydrolysis (W. H. Fishman, ed.), pp. 1–19, Academic Press, New York.
Stetten, M. R. 1970, Enzymatic synthesis of glycerol-1-phosphate. Elevation in diabetic and fasted animals, compared with glucose-6-phosphatase and related enzyme activities, Biochim. Biophys.Acta 208:394.
Taylor, W., and Scratcherd, T., 1963, Steroid metabolism in the cat. 2. Biliary and urinary excretion of metabolites of [4–14C]corticosteroid, Biochem. J. 86:114.
Tomlinson, G. A., and Yaffe, S. J., 1966, The formation of bilirubin and p-nitrophenylglucuronides by rabbit liver, Biochem. J. 99:507.
Träuble, H., and Sackmann, E., 1972, Studies of the crystalline-liquid phase transition of lipid mode membranes. III. Structure of a steroid-lecithin system below and above the lipid-phase transition, J. Am. Chem. Soc. 94:4499.
Vainio, H., 1973, Action of chaotropic agents on drug-metabolizing enzymes in hepatic microsomes, Biochim. Biophys. Acta 207:152.
Van Roy, F. P., and Heirwegh, K. P. M., 1968, Determination of bilirubin glucuronide and assay of glucuronyltransferase with bilirubin as acceptor, Biochem. J. 106:507.
Vessey, D. A., and Zakim, D., 1971, Regulation of microsomal enzymes by phospholipids. II. Activation of hepatic uridine diphosphate-glucuronyltransferase, J. Biol. Chem. 246:4649.
Vessey, D. A., and Zakim, D., 1972a, Regulation of microsomal enzymes by phospholipids IV. Species differences in the properties of microsomal UDP-glucuronyltransferase, Biochim. Biophys. Acta 268:61.
Vessey, D. A., and Zakim, D., 1972b, Regulation of microsomal enzymes by phospholipids V. Kinetic studies of hepatic uridine diphosphate glucuronyltransferase, J. Biol. Chem. 247:3023.
Vessey, D. A., and Zakim, D., 1974a, Membrane fluidity and the regulation of membrane-bound enzymes, in: Horizons in Biochemistry and Biophysics (Quagliariello, E., Palmieri, F., and Singer, T. P., eds.), pp. 137–174, Addison Wesley, Boston.
Vessey, D. A., and Zakim, D., 1974b, Stimulation of microsomal uridine diphosphate glucuronyl-transferase by glucuronic acid derivatives, Biochem. J. 139:243.
Vessey, D. A., and Zakim, D., 1975, Electron spin resonance studies of the microsomal membranes: The effect of perturbers of membrane structure, in preparation.
Vessey, D. A., Goldenberg, J., and Zakim, D., 1973a, Kinetic properties of microsomal UDP-glucuronyltransferase. Evidence for cooperative kinetics and activation by UDP-N-acetylglucos-amine, Biochim. Biophys. Acta 309:58.
Vessey, D. A., Goldenberg, J., and Zakim, D., 1973b, Differentiation of homologous forms of hepatic microsomal UDP-glucuronyltransferase II. Characterization of the bilirubin conjugating form, Biochim. Biophys. Acta 309:75.
Winsnes, A., 1969, Studies of the activation in vitro of glucuronyltransferase, Biochim. Biophys. Acta 191:279.
Winsnes, A., 1972, Kinetic properties of different forms of hepatic UDP-glucuronyltransferase, Biochim. Biophys. Acta 284:394.
Wong, K. P., and Lau, Y. K., 1970, Assay of UDPGlcUA pyrophosphatase and its relation to transglucuronidation, Biochim. Biophys. Acta 220:61.
Wood, G. G., and Graham, A. B., 1972, Effect of trypsin on the activity of microsomal glucuronyltransferase, Abstr. Commun. FEBS Meet. 8th:147.
Zakim, D., 1970, Regulation of microsomal enzymes by phospholipids I. The effect of phospholipases and phospholipids on glucose-6-phosphatase, J. Biol. Chem. 245:4943.
Zakim, D., and Vessey, D. A., 1972, Regulation of microsomal enzymes by phospholipids III. The role of —SH groups in the regulation of microsomal UDP-glucuronyltransferase, Arch. Biochem. Biophys. 148:97.
Zakim, D., and Vessey, D. A., 1973, Techniques for the characterization of UDP-glucuronyltransferase, glucose-6-phosphatase and other tightly-bound microsomal enzymes, Methods of Biochem. Anal. 21:1.
Zakim, D., and Vessey, D. A., 1974, Membrane dependence of uridine diphosphate glucuronyltransferase. Effect of the membrane on kinetic properties, Biochem. Soc. Trans. 2:1165.
Zakim, D., and Vessey, D. A., 1975a, Regulation of microsomal enzymes by phospholipids IX. Comparison of the effects of treatment with phospholipase A and Triton X-100 on the properties of microsomal UDP-glucuronyltransferase, Biochim. Biophys. Acta, in press.
Zakim, D., and Vessey, D. A., 1975b, Regulation of microsomal UDP-glucuronyltransferase: mechanism of activation by UDP-JV-acetylglucosamine, Biochem. Pharm., submitted.
Zakim, D., and Vessey, D. A., 1975c, An analysis of the effects of treatment with phospholipase C on the regulatory properties of UDP-glucuronyltransferase and the physical properties of membrane lipids, in preparation.
Zakim, D., and Vessey, D. A., 1975d, The effect of a temperature-induced phase change within membrane lipids on the regulatory properties of microsomal uridine diphosphate glucuronyltransferase, J. Biol. Chem. 250:342.
Zakim, D., Goldenberg, J., and Vessey, D. A., 1973a, Effects of metals on the properties of hepatic microsomal uridine-diphosphate glucuronyltransferase, Biochemistry 12:4068.
Zakim, D., Goldenberg, J., and Vessey, D. A., 1973b, Differentiation of homologous forms of hepatic microsomal UDP-glucuronyltransferase. I. Evidence for the glucuronidation of o-aminophenol and p-nitrophenol by separate enzymes, Biochim. Biophys. Acta 309:67.
Zakim, D., Goldenberg, J., and Vessey, D. A., 1973c, Regulation of microsomal enzymes by phospholipids. VI. Abnormal enzyme-lipid interactions in liver microsomes from Gunn rats, Biochim. Biophys. Acta 297:497.
Zakim, D., Goldenberg, J., and Vessey, D. A., 1973d, Influence of membrane-lipids on the regulatory properties of UDP-glucuronyltransferase, Eur. J. Biochem. 38:59.
Zakim, D., Goldenberg, J., and Vessey, D. A., 1973c, Kinetic properties of microsomal UDP-glucuronyltransferase. Regulation by metal ions, Biochem. Biophys. Res. Commun. 52:453.
Zhivkov, V., 1970, Measurement of uridine diphosphate glucuronic acid concentrations and synthesis in animal tissues, Biochem. J. 120:505.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1976 Plenum Press, New York
About this chapter
Cite this chapter
Zakim, D., Vessey, D.A. (1976). The Effects of Lipid-Protein Interactions on the Kinetic Parameters of Microsomal UDP-Glucuronyltransferase. In: Martonosi, A. (eds) The Enzymes of Bioligical Membranes. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2655-7_12
Download citation
DOI: https://doi.org/10.1007/978-1-4684-2655-7_12
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4684-2657-1
Online ISBN: 978-1-4684-2655-7
eBook Packages: Springer Book Archive