Influence of phenylalanines 77 and 138 on the stereospecificity of aryl sulfotransferase IV

Drug Metabolism and Disposition

Volumn 32, Issue 5, 2004, Pages 559-565

  Sheng, Jonathan J ^a   Saxena, Atmaja ^a   Duffel, Michael W ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 TETRALOL; ARYL SULFOTRANSFERASE; BENZYL ALCOHOL; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL INTERACTION; CHIRALITY; CONTROLLED STUDY; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; SEQUENCE HOMOLOGY; STEREOSPECIFICITY; SUBSTITUTION REACTION; SULFATION;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; CATALYSIS; MOLECULAR SEQUENCE DATA; PHENYLALANINE; RATS; STEREOISOMERISM; SULFOTRANSFERASES;

EID: 2042515581     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.32.5.559     Document Type: Article

References (32)

1. Bensadoun A and Weinstein D (1976) Assay of proteins in the presence of interfering materials. Anal Biochem 70:241-250.
2. Bidwell LM, McManus ME, Gaedigk A, Kakuta Y, Negishi M, Pedersen L, and Martin JL (1999) Crystal structure of human catecholamine sulfotransferase. J Mol Biol 293:521-530.
3. Brix LA, Barnett AC, Duggleby RG, Leggett B, and McManus ME (1999) Analysis of the substrate specificity of human sulfotransferases SULT1A1 and SULT1A3: site-directed mutagenesis and kinetic studies. Biochemistry 38:10474-10479.
4. Chen G, Baron J, and Duffel MW (1995) Enzyme- and sex-specific differences in the intralobular localizations and distributions of aryl sulfotransferase IV (tyrosine-ester sulfotransferase) and alcohol (hydroxysteroid) sulfotransferase a in rat liver. Drug Metab Dispos 23:1346-1353.
5. Chen X, Yang Y-S, Zheng Y, Martin BM, Duffel MW, and Jakoby WB (1992) Tyrosine-ester sulfotransferase from rat liver: bacterial expression and identification. Protein Expression Purif 3:421-426.
6. Dajani R, Cleasby A, Neu M, Wonacott AJ, Jhoti H, Hood AM, Modi S, Hersey A, Taskinen J, Cooke RM, et al. (1999) X-ray crystal structure of human dopamine sulfotransferase, SULT1A3. Molecular modeling and quantitative structure-activity relationship analysis demonstrate a molecular basis for sulfotransferase substrate specificity. J Biol Chem 274:37862-37868.
7. Dajani R, Hood AM, and Coughtrie MWH (1998) A single amino acid, glu146, governs the substrate specificity of a human dopamine sulfotransferase, SULT1A3. Mol Pharmacol 54:942-948.
8. Duffel MW (1994) Molecular specificity of aryl sulfotransferase IV (tyrosine-ester sulfotransferase) for xenobiotic substrates and inhibitors. Chem Biol Interact 92:3-14.
9. Duffel MW (1997) Sulfotransferases, in Comprehensive Toxicology, Volume 3, Biotransformation (Guengerich FP ed) pp 365-383, Elsevier Science Ltd., Oxford, UK.
10. Duffel MW, Binder TP, and Rao SI (1989) Assay of purified aryl sulfotransferase suitable for reactions yielding unstable sulfuric acid esters. Anal Biochem 183:320-324.
11. Duffel MW, Marshall AD, McPhie P, Sharma V, and Jakoby WB (2001) Enzymatic aspects of the phenol (aryl) sulfotransferases. Drug Metab Rev 33:369-395.
12. Falany CN (1997) Enzymology of human cytosolic sulfotransferases. FASEB J 11:206-216.
13. Gamage NU, Duggleby RG, Barnett AC, Tresillian M, Latham CF, Liyou NE, McManus ME, and Martin JL (2003) Structure of a human carcinogen-converting enzyme, SULT1A1. Structural and kinetic implications of substrate inhibition. J Biol Chem 278:7655-7662.
14. Glatt H, Boeing H, Engelke CE, Ma L, Kuhlow A, Pabel U, Pomplun D, Teubner W, and Meinl W (2001) Human cytosolic sulphotransferases: genetics, characteristics, toxicological aspects. Mutat Res 482:27-40.
15. Honma W, Kamiyama Y, Yoshinari K, Sasano H, Shimada M, Nagata K, and Yamazoe Y (2001) Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. Drug Metab Dispos 29:274-281.
16. Jakoby WB, Sekura RD, Lyon ES, Markus CJ, and Wang JL (1980) Sulfotransferases, in Enzymatic Basis of Detoxication (Jakoby WB ed) vol 2, pp 199-228, Academic Press, New York.
17. Kakuta Y, Pedersen LG, Carter CW, Negishi M, and Pedersen LC (1997) Crystal structure of estrogen sulphotransferase. Nat Struct Biol 4:904-908.
18. Kakuta Y, Petrotchenko EV, Pedersen LC, and Negishi M (1998) The sulfuryl transfer mechanism. Crystal structure of a vanadate complex of estrogen sulfotransferase and mutational analysis. J Biol Chem 273:27325-27330.
19. King RS, Sharma V, Pedersen LC, Kakuta Y, Negishi M, and Duffel MW (2000) Structure-function modeling of the interactions of N-alkyl-N-hydroxyanilines with rat hepatic aryl sulfotransferase IV. Chem Res Toxicol 13:1251-1258.
20. 4. Nature (Lond) 227:680-685.
21. Miller JA (1994) Sulfonation in chemical carcinogenesis-history and present status. Chem Biol Interact 92:329-341.
22. Nagata K and Yamazoe Y (2000) Pharmacogenetics of sulfotransferase. Annu Rev Pharmacol Toxicol 40:159-176.
23. Negishi M, Pedersen LG, Petrotchenko E, Shevtsov S, Gorokhov A, Kakuta Y, and Pedersen LC (2001) Structure and function of sulfotransferases. Arch Biochem Biophys 390:149-157.
24. Pai TG, Oxendine I, Sugahara T, Suiko M, Sakakibara Y, and Liu MC (2003) Structure-function relationships in the stereospecific and manganese-dependent 3,4-dihydroxyphenylalanine/tyrosine-sulfating activity of human monoamine-form phenol sulfotransferase, SULT1A3. J Biol Chem 278:1525-1532.
25. Pedersen LC, Petrotchenko E, Shevtsov S, and Negishi M (2002) Crystal structure of the human estrogen sulfotransferase-PAPS complex: evidence for catalytic role of Ser137 in the sulfuryl transfer reaction. J Biol Chem 277:17928-17932.
26. Petrotchenko EV, Doerflein ME, Kakuta Y, Pedersen LC, and Negishi M (1999) Substrate gating confers steroid specificity to estrogen sulfotransferase. J Biol Chem 274:30019-30022.
27. Rao SI and Duffel MW (1991) Benzylic alcohols as stereospecific substrates and inhibitors for aryl sulfotransferase. Chirality 3:104-111.
28. Sekura RD, Sato K, Cahnmann HJ, Robbins J, and Jakoby WB (1981) Sulfate transfer to thyroid hormones and their analogs by hepatic aryl sulfotransferases. Endocrinology 108:454-456.
29. Sheng J, Sharma V, and Duffel MW (2001) Measurement of aryl and alcohol sulfotransferase activity, in Current Protocols in Toxicology, pp 4.5.1-4.5.9, John Wiley & Sons, Inc., New York.
30. Weinshilboum R and Otterness D (1994) Sulfotransferase enzymes, in Handbook of Experimental Pharmacology (Kauffman FC ed) pp 45-78, Springer-Verlag, Berlin.
31. Weinshilboum RM, Otterness DM, Aksoy IA, Wood TC, Her C, and Raftogianis RB (1997) Sulfation and sulfotransferases 1: sulfotransferase molecular biology: cDNAs and genes. FASEB J 11:3-14.
32. Yoshinari K, Petrotchenko EV, Pedersen LC, and Negishi M (2001) Crystal structure-based studies of cytosolic sulfotransferase. J Biochem Mol Toxicol 15:67-75.