Identification of residues that confer sugar selectivity to UDP-glycosyltransferase 3A (UGT3A) enzymes

Journal of Biological Chemistry

Volumn 287, Issue 29, 2012, Pages 24122-24130

  Meech, Robyn ^a   Rogers, Anne ^a   Zhuang, Lizhe ^a   Lewis, Benjamin C ^a   Miners, John O ^a   Mackenzie, Peter I ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ENZYMES; GLUCOSE; MAMMALS; MOLECULES;

GLYCOSYL TRANSFERASE; HOMOLOGY MODELS; NON-HUMAN PRIMATE; OPTIMAL ALIGNMENTS; SEQUENCE ANALYSIS; SIGNATURE SEQUENCES; STRUCTURAL MODELING; UDP-GLUCURONIC ACID;

SUGAR INDUSTRY;

ASPARAGINE; GLYCOSYLTRANSFERASE; HISTIDINE; PHENYLALANINE; SUGAR; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE GLUCOSE; URIDINE DIPHOSPHATE GLYCOSYLTRANSFERASE 3A1; URIDINE DIPHOSPHATE GLYCOSYLTRANSFERASE 3A2; URIDINE DIPHOSPHATE N ACETYLGLUCOSAMINE; URIDINE DIPHOSPHATE SUGAR;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; EMBRYO; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ENZYME STRUCTURE; GENE EXPRESSION; GENE MUTATION; GENETIC ANALYSIS; HUMAN; HUMAN CELL; MOLECULAR MODEL; MOUSE; MUTANT; NEWBORN; NONHUMAN; PRIORITY JOURNAL; SEQUENCE HOMOLOGY;

MAMMALIA; PRIMATES;

EID: 84863797329     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M112.343608     Document Type: Article

References (28)

1. Mackenzie, P. I., Owens, I. S., Burchell, B., Bock, K. W., Bairoch, A., Bélanger, A., Fournel-Gigleux, S., Green, M., Hum, D. W., Iyanagi, T., Lancet, D., Louisot, P., Magdalou, J., Chowdhury, J. R., Ritter, J. K., Schachter, H., Tephly, T. R., Tipton, K. F., and Nebert, D. W. (1997) The UDP-glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7, 255-269 (Pubitemid 27358064)
2. Meech, R., and Mackenzie, P. I. (1997) Structure and function of uridine diphosphate glucuronosyltransferases. Clin. Exp. Pharmacol. Physiol. 24, 907-915 (Pubitemid 27494298)
3. Tukey, R. H., and Strassburg, C. P. (2000) Human UDP- glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxicol. 40, 581-616 (Pubitemid 30340694)
4. Radominska-Pandya, A., Czernik, P. J., Little, J. M., Battaglia, E., and Mackenzie, P. I. (1999) Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab. Rev. 31, 817-899
5. Miners, J. O., and Mackenzie, P. I. (1991) Drug glucuronidation in humans. Pharmacol. Ther. 51, 347-369
6. Mackenzie, P. I., Bock, K. W., Burchell, B., Guillemette, C., Ikushiro, S., Iyanagi, T., Miners, J. O., Owens, I. S., and Nebert, D. W. (2005) Nomenclature update for the mammalian UDP-glycosyltransferase (UGT) gene superfamily. Pharmacogenet. Genomics 15, 677-685 (Pubitemid 41345319)
7. Ritter, J. K., Chen, F., Sheen, Y. Y., Tran, H. M., Kimura, S., Yeatman, M. T., and Owens, I. S. (1992) A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini. J. Biol. Chem. 267, 3257-3261
8. Mackenzie, P. I., Rogers, A., Treloar, J., Jorgensen, B. R., Miners, J. O., and Meech, R. (2008) Identification of UDP-glycosyltransferase 3A1 as a UDP-N-acetylglucosaminyltransferase. J. Biol. Chem. 283, 36205-36210
9. Mackenzie, P. I., Rogers, A., Elliot, D. J., Chau, N., Hulin, J. A., Miners, J. O., and Meech, R. (2011) The novel UDP-glycosyltransferase 3A2: cloning, catalytic properties, and tissue distribution. Mol. Pharmacol. 79, 472-478
10. Mackenzie, P., Little, J. M., and Radominska-Pandya, A. (2003) Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7. Biochem. Pharmacol. 65, 417-421 (Pubitemid 36084558)
11. Tang, C., Hochman, J. H., Ma, B., Subramanian, R., and Vyas, K. P. (2003) Acyl glucuronidation and glucosidation of a new and selective endothelin ETA receptor antagonist in human liver microsomes. Drug Metab. Dispos. 31, 37-45 (Pubitemid 36735256)
12. Senafi, S. B., Clarke, D. J., and Burchell, B. (1994) Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem. J. 303, 233-240 (Pubitemid 24302924)
13. Bosio, A., Binczek, E., Le Beau, M. M., Fernald, A. A., and Stoffel, W. (1996) The human gene CGT encoding the UDP-galactose:ceramide galactosyltransferase (cerebroside synthase): cloning, characterization, and assignment to human chromosome 4, band q26. Genomics 34, 69-75 (Pubitemid 26159882)
14. Hobbs, S., Jitrapakdee, S., and Wallace, J. C. (1998) Development of a bicistronic vector driven by the human polypeptide chain elongation factor 1α promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins. Biochem. Biophys. Res. Commun. 252, 368-372 (Pubitemid 28542893)
15. Udomuksorn, W., Elliot, D. J., Lewis, B. C., Mackenzie, P. I., Yoovathaworn, K., and Miners, J. O. (2007) Influence of mutations associated with Gilbert and Crigler-Najjar type II syndromes on the glucuronidation kinetics of bilirubin and other UDP-glucuronosyltransferase 1A substrates. Pharmacogenet. Genomics 17, 1017-1029 (Pubitemid 351339486)
16. Eddy, S. R. (1998) Profile hidden Markov models. Bioinformatics 14, 755-763
17. Radominska-Pandya, A., Bratton, S. M., Redinbo, M. R., and Miley, M. J. (2010) The crystal structure of human UDP-glucuronosyltransferase 2B7 C-terminal end is the first mammalian UGT target to be revealed: the significance for human UGTs from both the 1A and 2B families. Drug Metab. Rev. 42, 133-144
18. Powell, M. J. D. (1977) Beyond symmetric Broyden for updating quadratic models in minimization without derivatives. Mathematical Programming 12, 241-254
19. Mayo, S. L., Olafson, B. D., and Goddard, W. A. (1990) DREIDING: a generic force field for molecular simulations. J. Phys. Chem. 94, 8897-8909
20. Bowalgaha, K., Elliot, D. J., Mackenzie, P. I., Knights, K. M., Swedmark, S., and Miners, J. O. (2005) S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br. J. Clin. Pharmacol. 60, 423-433 (Pubitemid 41428474)
21. Meech, R., and Mackenzie, P. I. (2010) UGT3A: novel UDP- glycosyltransferases of the UGT superfamily. Drug Metab. Rev. 42, 45-54
22. Miley, M. J., Zielinska, A. K., Keenan, J. E., Bratton, S. M., Radominska-Pandya, A., and Redinbo, M. R. (2007) Crystal structure of the cofactor-binding domain of the human phase II drug-metabolism enzyme UDP-glucuronosyltransferase 2B7. J. Mol. Biol. 369, 498-511 (Pubitemid 46678060)
23. Battaglia, E., Terrier, N., Mizeracka, M., Senay, C., Magdalou, J., Fournel-Gigleux, S., and Radominska-Pandya, A. (1998) Interaction of periodateoxidized UDP-glucuronic acid with recombinant human liver UDP-glucuronosyltransferase 1A6. Drug Metab. Dispos. 26, 812-817 (Pubitemid 28376442)
24. Patana, A. S., Kurkela, M., Goldman, A., and Finel, M. (2007) The human UDP-glucuronosyltransferase: identification of key residues within the nucleotide-sugar binding site. Mol. Pharmacol. 72, 604-611 (Pubitemid 47347295)
25. Xiong, Y., Patana, A. S., Miley, M. J., Zielinska, A. K., Bratton, S. M., Miller, G. P., Goldman, A., Finel, M., Redinbo, M. R., and Radominska-Pandya, A. (2008) The first aspartic acid of the DQxD motif for human UDP-glucuronosyltransferase 1A10 interacts with UDP-glucuronic acid during catalysis. Drug Metab. Dispos. 36, 517-522 (Pubitemid 351397976)
26. Kubo, A., Arai, Y., Nagashima, S., and Yoshikawa, T. (2004) Alteration of sugar donor specificities of plant glycosyltransferases by a single point mutation. Arch. Biochem. Biophys. 429, 198-203 (Pubitemid 39099251)
27. Offen, W., Martinez-Fleites, C., Yang, M., Kiat-Lim, E., Davis, B. G., Tarling, C. A., Ford, C. M., Bowles, D. J., and Davies, G. J. (2006) Structure of a flavonoid glucosyltransferase reveals the basis for plant natural product modification. EMBO J. 25, 1396-1405
28. Osmani, S. A., Bak, S., Imberty, A., Olsen, C. E., and Møller, B. L. (2008) Catalytic key amino acids and UDP-sugar donor specificity of a plant glucuronosyltransferase, UGT94B1: molecular modeling substantiated by site-specific mutagenesis and biochemical analyses. Plant Physiol. 148, 1295-1308 (Pubitemid 352847492)