Sterol methyl transferase. Evidence for successive C-methyl transfer reactions generating Δ24(28)- and Δ25(27)-olefins by a single plant enzyme

Tetrahedron Letters

Volumn 43, Issue 39, 2002, Pages 7017-7021

  Dennis, Allen L ^a   Nes, W David ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Cycloartenol; Methyl transferase; Phytosterol; Sitosterol; Soybean; Stereochemistry; Sterol

Indexed keywords

24 METHYLENE CYCLOARTENOL; ALKENE DERIVATIVE; CYCLOARTENOL; METHYLTRANSFERASE; STEROL DERIVATIVE; STEROL METHYLTRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CONTROLLED STUDY; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; METHYLATION; NONHUMAN; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SEQUENCE ALIGNMENT; SOYBEAN; STEADY STATE; STEREOCHEMISTRY;

ESCHERICHIA COLI; GLYCINE MAX;

EID: 0037163251     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01550-2     Document Type: Article

References (33)

1. Goad L.J., Lenton F.F., Knapp F.F., Goodwin T.W. Lipids. 9:1974;582.
2. Nes W.R., Nes W.D. Lipids in Evolution. 1980;97-244 Plenum Press, New York.
3. Hartmann M.-A. Trends Plant Sci. 3:1999;17.
4. Clouse S.D. Plant J. 10:1996;1.
5. (a) Nes, W. D. Biochim. Biophys. Acta 2000, 1529, 63 [reviews the enzymology of SMT action]; (b) Janssen, G. G.; Kalinowska, M.; Norton, R. A.; Nes, W. D. In Physiology and Biochemistry of Sterols; Patterson, G. W.; Nes, W. D., Eds.; American Oil Chemists' Society Press Champaign, 1991; pp. 83-117.
6. (a) Nes, W. D. Biochim. Biophys. Acta 2000, 1529, 63 [reviews the enzymology of SMT action]; (b) Janssen, G. G.; Kalinowska, M.; Norton, R. A.; Nes, W. D. In Physiology and Biochemistry of Sterols; Patterson, G. W.; Nes, W. D., Eds.; American Oil Chemists' Society Press Champaign, 1991; pp. 83-117.
7. Bouvier-Nave P., Husselstein T., Benveniste P. Eur. J. Biochem. 256:1998;88.
8. Grebenok R.J., Galbraith D.W., Penna D.D. Plant Mol. Biol. 34:1997;891.
9. Shi J., Gonzales R.A., Bhattacharyya K. J. Biol. Chem. 271:1996;9384
10. (d) SMT genes sequences have been deposited in the GenBank which should be consulted for detailed analysis.
11. Fonteneau P., Hartmann-Bouillon M.A., Benveniste P. Plant Sci. Lett. 10:1977;147.
12. Rahier A., Narula A.S., Benveniste P., Schmitt P. Biochem. Biophys. Res. Commun. 92:1980;20.
13. Rahier A., Genot J.-C., Schuber F., Benveniste P., Narula A.S. J. Biol. Chem. 259:1984;15215.
14. Goodwin T.W. Stumpf P.K., The Biochemistry of Plants: A Comprehensive Treatise. 4:1980;485-507 Academic Press, New York.
15. Seo S., Uomori A., Yashimura Y., Takeda K. J. Am. Chem. Soc. 105:1983;6343.
16. Nicotra F., Ronchetti F., Russo G., Lugara G., Castellato M. J. Chem. Soc., Chem. Commun. 1987;1876.
17. Arigoni D. Ciba Found. Symp. 60:1978;243.
18. Okuzumi T., Kaji Y., Hamada H., Fujimoto Y. Tetrahedron Lett. 41:2000;3623.
19. Yagi T., Morisaki M., Kushiro T., Yoshida H., Fujimoto Y. Phytochemistry. 41:1996;1057.
20. Guo D., Jia Z., Nes W.D. J. Am. Chem. Soc. 118:1996;8507.
21. Tong Y., McCourt B.S., Guo D., Mangla A.T., Zhou W.-x., Jenkins M.D., Zhou W., Lopez M., Nes W.D. Tetrahedron Lett. 38:1997;6115.
22. Nes W.D., McCourt B.S., Marshall J.A., Ma J., Dennis A.L., Lopez M., Li H., He L. J. Org. Chem. 64:1999;1535. [in this study we generated a Y81F mutant of the yeast SMT and found that substrate specificity and the degree of C-methylation can be modified to mimic plant SMT action similar to the soybean catalysis reported here].
23. Nes W.D., McCourt B.S., Shou W-x., Marshall J.A., Peek L.-A., Brennan M. Arch. Biochem. Biophys. 353:1998;297.
24. Guo D., Venkatramesh M., Nes W.D. Lipids. 30:1995;203.
25. Nes W.D., Xu S., Haddon W.F. Steroids. 53:1988;533.
26. Villoutreix H.J., Chapelle G.S. Can. J. Microbiol. 29:1983;606.
27. Kaneshiro E.S., Amit Z., Swonger M.M., Kreishman G.P., Brooks E.E., Kreishman K., Jayasimhulu K., Parish E.J., Sun H., Kzito S.A., Beach D.H. Proc. Natl. Acad. Sci. USA. 96:1999;97.
28. Kalinowska M., Nes W.R., Crumley F.G., Nes W.D. Phytochemistry. 29:1990;3427.
29. Goad L.J., Akihisa T. Analysis of Sterols. 1997;364-395 Blackie Academic & Professional, London.
30. Nes W.D., Koike K., Jia Z., Sakamoto Y., Satou T., Nikaido T., Griffin J.F. J. Am. Chem. Soc. 120:1998;5970.
31. Artaud J.M.C., Isse I.C., Zahara J.P., Estienne J. Analusis. 8:1980;1269.
32. Marshall J.A., Dennis A.L., Kumazawa T., Haynes A.M., Nes W.D. Phytochemistry. 58:2001;423.
33. Fenner G.P., Patterson G.W., Koines P.M. Lipids. 21:1986;48.