Role of Serine 286 in cosubstrate binding and catalysis of a flavonol O-methyltransferase

Biochemistry and Cell Biology

Volumn 82, Issue 5, 2004, Pages 531-537

  Kornblatt, Jack ^a   Muzac, Ingrid ^a   Lim, Yoongho ^b   Joong, Hoon Ahn ^b   Ibrahim, Ragai K ^a  

^a Gina Cody School of Engineering and Computer Science   (Canada)

^b Konkuk University   (South Korea)

Author keywords

Flavonoids; O methyltransferase; Photoaffinity labeling

Indexed keywords

AMINO ACIDS; BINDING ENERGY; CALORIMETRY; CATALYSIS; CLONING; CONFORMATIONS; DNA; MUTAGENESIS; TITRATION;

CIRCULAR DICHROISM SPECTRA; COSUBSTRATE BINDING; FLAVONOID COMPOUNDS; HYDROXYL GROUPS;

ENZYMES;

ALANINE; AMINO ACID; CHALCONE DERIVATIVE; COMPLEMENTARY DNA; FLAVONOID; FLAVONOL DERIVATIVE; FLAVONOL O METHYLTRANSFERASE; HYDROXYL GROUP; LEUCINE; LYSINE; RECOMBINANT PROTEIN; S ADENOSYLMETHIONINE; SERINE; THREONINE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; DNA ISOLATION; ENZYME ACTIVITY; ENZYME SUBUNIT; METHYLATION; MICROCALORIMETRY; MOLECULAR CLONING; NUCLEOTIDE SEQUENCE; PHOTOAFFINITY LABELING; SAXIFRAGACEAE; TITRIMETRY;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; CATALYSIS; DNA, COMPLEMENTARY; FLAVONOLS; METHYLATION; METHYLTRANSFERASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PLANT PROTEINS; PLANTS; PROTEIN BINDING; SERINE;

CHRYSOSPLENIUM AMERICANUM; SAXIFRAGACEAE;

EID: 9244224178     PISSN: 08298211     EISSN: None     Source Type: Journal    
DOI: 10.1139/o04-054     Document Type: Article

References (25)

1. Bohm, B.A. 1998. Flavonoid functions in nature. In Introduction to flavonoids. Chemistry and biochemistry of organic natural products. Vol. 2. HarwoodAcademic Publishers, Amsterdam, Netherlands, pp. 339-364.
2. Bradford, M.M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254.
3. De Luca, V., and Ibrahim, R.K. 1985. Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of 3-, 6-, 7- and 4′- O-methyl-transferases. Arch. Biochem. Biophys. 238: 496-605.
4. French, C.J., Elder, M., Leggett, R, Ibrahim, R.K., and Towers, G.H.N. 1991. Flavonoids inhibit mosaic virus infectivity. Can. J. Plant Pathol. 13: 1-6.
5. Gauthier, A., Gulick, P.G., and Ibrahim, R.K. 1996. cDNA cloning and characterization of an S-adenosyl-L-methionine:partially methylated flavonal 3′/5′-O-methylransferase from Chrysosplenium americanum. Plant Mol. Biol. 32: 1163-1169.
6. Gauthier, A., Gulick, P.G., and Ibrahim, R.K. 1998. Characterization of two cDNA clones which encode O-methyltransferases for the methylation of both flavonoid and phenylpropanoid compounds. Arch. Biochem. Biophys. 351: 243-249.
7. Hofsteenge, J., Moldow, C., Vicentini, A.M., Jarai-Kote, Z., and Neumann, U. 1998. A single amino acid substitution changes ribonuclease 4 from a uridine-specific to a cytidine-specific enzyme. Biochemistry, 37: 9250-9257.
8. Hu, T., Chang, S., and Hsieh, T. 1988. Identifying Lys359 as a critical residue for the ATP-dependent reactions of Drosophila DNA topoisomerase II. J. Biol. Chem. 273: 9586-9592.
9. Ibrahim, R.K., and Muzac, I. 2000. The methyltransferase gene superfamily: a tree with multiple branches. In Evolution of metabolic pathways. Edited by J.T. Romeo, R.K. Ibrahim, L, Varin, and V. De Luca. Pergamon, Amsterdam, Netherlands, pp. 349-384.
10. Iwano, H., Yokota, H., Ohgiya, S., Yotumoto, N., and Yuasa, A. 1997. A critical amino acid residue, Asp446 in UDP-glucuronosyltransferase. Biochem. J. 325: 587-591.
11. Johnson, E.T., Ryu, S, Yi, H., Shin, B., Cheong, H., and Choi, G. 2001. Alteration of a single amino acid changes the substrate specificity of dihydroflavonol 4-reductase. Plant J. 25: 325-333.
12. Kittendorf, J.D., Sgraja, T., Reuter, K., Klebe, G., and Garcia, G.A. 2003. An essential role for aspartate 264 in catalysis by tRNA-guanine transglycosylase from Escherichia coli. J. Biol. Chem. 278: 42 369-42 376.
13. Kornblatt, M.J., Al-Ghanim, A., and Kornblatt, J.A. 1996. The effects of sodium perchlorate on rabbit muscle enolase. Spectral characterization of the monomer. Eur. J. Biochem. 236: 78-84.
14. Laemmli, U.K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227: 668-685.
15. Mayer, C., Zechel, D.L., Reid, S.P., Warren, R.A., and Withers, S.G. 2000. The E358S mutant of Agrobacterium sp. β-glucosidase is a gratly improved glycosynthase. FEBS Lett. 466: 40-44.
16. McKinney, M.K., and Gravatt, B.F. 2003. Evidence for distinct roles in catalysis for residues of the Serine-Serine-Lysine catalytic triad of fatty acid amide hydrolase. J. Biol. Chem. 278: 37 393-37 399.
17. Pollock, V.V., and Barber, M.J. 2000. Serine 121 is an essential amino acid for biotin sulfoxide reductase functionality. J. Biol. Chem. 275: 35 086-35 090.
18. Schröder, G., and Schröder, J. 1992. A single change of histidine to glutamine alters the substrate preference of a stilbene synthase. J. Biol. Chem. 267: 20 558-20 560.
19. Schubert, H.L., Blumenthal, R.M., and Cheng, X. 2003. Many paths to methyl transfer: a chronicle of convergence. Trends Biochem. Sci. 28: 329-335.
20. Séguin, J., Muzac, I., and Ibrahim, R.K. 1998. Purification and immunological characterization of a recombinant trimethylflavonol 3′-O-methyltransferase. Phytochemistry (Oxf.), 49: 319-325.
21. Som, S., and Friedman, S. 1990. Direct photolabeling of Eco RII methyltransferase with S-adenosyl-L-methionine. J. Biol. Chem. 265: 4278-4283.
22. Yamamoto, F., and McNeill, P.D. 1996. Amino acid residue at codon 268 determines both activity and nucleotide-sugar donor substrate specificity of human histo-blood group A and B transferases: in vitro mutagenesis study. J. Biol. Chem. 271: 10 515-10 520.
23. Zhu, B.T., Ezell, E.L., and Liehr, J.G. 1994. Catechol-O- methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo. J. Biol. Chem. 269: 292-299.
24. Zubieta, C., He, Xian-Zhi, Dixon, R.A., and Noel, J.P. 2001. Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltansferases. Nature Struct. Biol. 8: 271-279.
25. Zubieta, C., Kota, P., Ferrer, J.L., Dixon, R.A., and Noel, J.P. 2002. Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase. Plant Cell, 14: 1265-1277.