Yeast sterol C24-methyltransferase: Role of highly conserved tyrosine-81 in catalytic competence studied by site-directed mutagenesis and thermodynamic analysis

Archives of Biochemistry and Biophysics

Volumn 477, Issue 2, 2008, Pages 313-323

  Nes, W David ^a   Jayasimha, Pruthvi ^a   Song, Zhihong ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Aliphatic amino acids; Cation interactions; Energy profiles; Mechanism based inactivation; Mutagenesis; Sterol enzymology; Sterol methyl transferase; Transition state analogs

Indexed keywords

24,25 EPIMINOLANOSTEROL; 25 AZALANOSTEROL; 26,27 DEHYDROZYMOSTEROL; ALANINE; ALIPHATIC CARBOXYLIC ACID; AMINO ACID; AMINO ACID DERIVATIVE; AROMATIC CARBOXYLIC ACID; ERGOSTEROL; ISOLEUCINE; LEUCINE; METHYLTRANSFERASE; PHENYLALANINE; STEROL C24 METHYLTRANFERASE; TRYPTOPHAN; TYROSINE; UNCLASSIFIED DRUG; VALINE; ZYMOSTEROL;

ALKYLATION; ARTICLE; CATALYSIS; DNA SEQUENCE; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME SUBSTRATE; GENE MUTATION; HYDROGEN BOND; METHYLATION; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; SACCHAROMYCES CEREVISIAE; SITE DIRECTED MUTAGENESIS; THERMODYNAMICS; YEAST;

CATALYSIS; COMPUTER SIMULATION; CONSERVED SEQUENCE; ENZYME ACTIVATION; HUMANS; METHYLTRANSFERASES; MODELS, CHEMICAL; MODELS, MOLECULAR; MUTAGENESIS, SITE-DIRECTED; MUTATION; PROTEIN CONFORMATION; SACCHAROMYCES CEREVISIAE; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

SACCHAROMYCES CEREVISIAE;

EID: 50149090164     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2008.05.016     Document Type: Article

References (51)

1. Benveniste P. Annu. Rev. Plant Biol. 55 (2004) 429-457
2. Lindsey K., Pullen M.L., and Topping J.F. Trends Plant Sci. 8 (2003) 521-525
3. Jayasimha P., Bowman C.B., Pedroza J.M., and Nes W.D. Rec. Adv. Phytochem. 40 (2006) 211-251
4. Iwaki T., Lefuji H., Hiraga Y., Hosomi A., Morita T., and Giga-Hama Y. Microbiology 154 (2008) 830-841
5. Patterson G.W. Am. Chem. Soc. Symp. Ser 562 (1994) 90-103
6. Bloch K.E. CRC Crit. Rev. Biochem. 14 (1983) 47-82
7. Sharma S.C. FEMS Yeast Res. 6 (2006) 1047-1051
8. Simons K., and Ikonen E. Nature 387 (1997) 569-572
9. Parks L.W., Crowley J.H., Leak F.W., Smith S.J., and Tomeo M.E. Crit. Rev. Biochem. Mol. Biol. 34 (1999) 399-404
10. Roberts C.W., McLeod R., Rice D.W., Ginger M., Chance M.L., and Goad L.J. Mol. Biochem. Parasitol. 126 (2003) 129-142
11. Burbiel J., and Bracher F. Steroids 68 (2003) 587-594
12. Lepesheva G.I., Ott R.D., Hargrove T.Y., Kleshchenko Y.Y., Schuster I., Nes W.D., Hill G.C., Villata F., and Waterman M.R. Chem. Biol. 14 (2007) 1-11
13. Song Z., and Nes W.D. Lipids 42 (2007) 15-33
14. Rodriques J.C.F., Bernardes C.F., Visbal G., Urbina J.A., Vercesi A.E., and Souza W.D. Protist 158 (2007) 447-456
15. Visbal G., San-Blas G., Murgich J., and Franco H. Curr. Drug Targets Infect. Disord. 5 (2005) 1-16
16. Kaneshiro E.S. Drug Resist. Updat. 5 (2002) 259-268
17. Beuchet P., Dherbomez M., Elkiel L., Charles G., and Letourneux Y. Bioorgan. Med. Chem. Lett. 9 (1999) 1599-1600
18. Acuna-Johnson A.P., Oehlschlager A.C., Pierce A.M., Pierce H.D., and Czyzwska Jr. E.K. Bioorgan. Med. Chem. 5 (1997) 821-832
19. Barrett-Bee K., and Dixon G. Acta Biochim. Polon. 42 (1995) 465-480
20. Nes W.D. Phytochemistry 64 (2003) 73-95
21. Lorente S.O., Rodriques J.C.F., Jimenez C.J., Joyce-Menekse M., Rodriques C., Croft S.L., Yardley V., de Luca-Fradley K., Ruiz-Perez L.M., Urbina J., de Souza W., Pacanowska D.G., and Gilbert I.H. Antimicrob. Agents Chemother. 48 (2004) 2937-2950
22. Simons V., Morissey J.P., Latijhouwers M., Csukai M., Cleaver A., Yarrow C., and Osbourn A. Antimicrob. Agents Chemother. 50 (2006) 2732-2740
23. Ator M.A., Schmidt S.J., Adams J.L., Dolle R.E., Kruse L.I., Frey C.L., and Barone J.M. J. Med. Chem. 35 (1992) 100-106
24. Oehlschlager A.C., Angus R.H., Pierce A.M., Pierce H.D., and Srinivasan R. Biochemistry 23 (1984) 3582-3589
25. Janssen G.G., and Nes W.D. J. Biol. Chem. 267 (1992) 25856-25863
26. Rahier A., C Genot J., Schuber F., Benveniste P., and Narula A.S. J. Biol. Chem. 259 (1984) 5215-5223
27. Venkatramesh M., Guo D., Harman J.G., and Nes W.D. Lipids 31 (1996) 373-377
28. Nes W.D., Marshall J.A., Jia Z., Jaradat T.T., Song Z., and Jayasimha P. J. Biol. Chem. 277 (2002) 42549-42556
29. Nes W.D., McCourt B.S., Marshall J.A., Dennis A.L., Lopez M., and Le H. J. Org. Chem. 64 (1999) 1535-1542
30. Nes W.D., Sinha A., Jayasimha P., Zhou W., Song Z., and Dennis A.L. Arch. Biochem. Biophys. 448 (2006) 23-30
31. Nes W.D., Jayasimha P., Zhou W., Kanagasabai R., Jin C., Jaradat T.T., Shaw R.W., and Bujnicki J.M. Biochemistry 43 (2004) 569-776
32. K. Ganapathy, C. W. Jones, C. M. Stephens, T. Vatsyayan, J. M. Marshall, W. D. Nes, Biochim. Biophys. Acta, in press.
33. Lamb D.C., Kelly D.E., White T.C., and Kelly S.L. Antimicrob. Agents Chemother. 44 (2000) 63-67
34. Nes W.D., Guo G., and Zhou W. Arch. Biochem. Biophys. 342 (1997) 68-81
35. Le P., and Nes W.D. Chem. Phys. Lipids 40 (1986) 57-69
36. Zhou W., Guo D., and Nes W.D. Tetrahedron Lett. 37 (1996) 1339-1342
37. Nes W.D., McCourt B.S., Marshall J.A., Ma J., Peek L.-A., and Brennan M. Arch. Biochem. Biophys. 353 (1998) 297-311
38. Copeland R.A. Enzymes. second ed. (2000), Wiley-VCH, New York pp. 23-306
39. Snider M.J., Gaunitz S., Ridgeway C., Short S.A., and Wolfenden R. Biochemistry 39 (2000) 9746-9753
40. Segel I.H. Enzyme Kinetics (1993), Wiley Interscience Publ., New York pp. 926-942
41. Houck W.J., and Pollack R.M. J. Am. Chem. Soc. 125 (2003) 10206-10212
42. Jackson S.E., and Fersht A.R. Biochemistry 32 (1993) 13909-13916
43. Taton M., Husselstein T., Benveniste P., and Rahier A. Biochemistry 29 (2000) 01-711
44. Hishino T., and Sato T. Chem. Commun. (2002) 291-301
45. Segua M.J.R., Jackson B.E., and Matsuda S.E.T. Nat. Prod. Rep. (2003) 304-317
46. Abe I. Nat. Prod. Rep. (2007) 1311-1331
47. Venkatramesh M., Guo D., Jia Z., and Nes W.D. Biochim. Biophys. Acta 1299 (1996) 313-324
48. Nes W.D., Song Z., Dennis A.L., Zhou W., Nam J., and Miller M. J. Biol. Chem. 278 (2003) 34505-34516
49. Albery W.J., and Knowles J.R. Biochemistry 15 (1976) 5631-5640
50. Vedula L.S., Rynkiewicz M.J., Pyun H.-J., Coates R.M., Cane D.E., and Christianson D.W. Biochemistry 44 (2005) 6153-6163
51. O'Maille P.O., Chappell J., and Noel J.P. Arch. Biochem. Biophys. 448 (2006) 73-82