Mechanism-based active site modification of sterol methyl transferase by tritium-labeled 26-homocholesta-8,14,24-trien-26-yn-3β-ol

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8575-8578

  Nes, W David ^a   Marshall, Julie A ^a   Zhou, Wen ^a   He, Ling ^a   Dennis, Allen L ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; METHYLTRANSFERASE; S ADENOSYLMETHIONINE; TRITIUM; ZYMOSTEROL;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME MODIFICATION; INHIBITION KINETICS; NONHUMAN; SACCHAROMYCES CEREVISIAE;

SACCHAROMYCES CEREVISIAE; TRITIUM;

EID: 0032547973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01961-3     Document Type: Article

References (20)

1. 1. Akihisa, T.; Kokke, W.C.M.C.; Tamura, T. In Physiology and Biochemistry of Sterols ; Patterson, G.; Nes, W. D., Eds.; Amer. Oil Chem. Soc. Press: Champaign, 1992; pp. 172-228; Nes, W. R.; McKean, M.L. Biochemistry of Steroids and Other Isopentenoids; University Park Press: Baltimore, 1977, pp. 325-533.
2. 1. Akihisa, T.; Kokke, W.C.M.C.; Tamura, T. In Physiology and Biochemistry of Sterols ; Patterson, G.; Nes, W. D., Eds.; Amer. Oil Chem. Soc. Press: Champaign, 1992; pp. 172-228; Nes, W. R.; McKean, M.L. Biochemistry of Steroids and Other Isopentenoids; University Park Press: Baltimore, 1977, pp. 325-533.
3. 2. (a) Bloch, K. E. CRC Crit. Rev. Biochem. 1982, 14, 47-92;
4. (b) Nes, W.D. ACS Symp. Ser. 1987, 325, 304-238.;
5. (c) Meudt, W. J. ACS Symp. Ser. 1987, 325, 53-75.
6. 3. (a) Nes, W.D.; Guo, D.; Zhou, W. Arch. Biochem. Biophys. 1997, 342, 68-81;
7. (b) Venkatramesh, M.; Guo, D.; Jia, Z.; Nes, W.D. Biochim. Biophys. Acta 1996, 1299, 313-324;
8. (c) Ator, M. A.; Schmidt, S. J.; Adams, J.L.; Dolle, R.E. Biochemistry 1989, 28, 9633-9640.;
9. (d) Rahier, A.S.; Genot, J-C.; Schuber, F.; Benveniste, P.; Narula, A.S. J. Biol. Chem. 1984, 259, 15215-1522;
10. (e) Oehlschlager, A.C.; Angus, R. H.; Pierce, A.M., Pierce, H.D.; Srinivasan, R. Biochemistry 1984, 23, 3582-3589.
11. 4. (a) Venkatramesh, M.; Guo, D.; Harman, J. G.; Nes, W. D. Lipids 1996; 31, 373-377.;
12. (b) Shi, J.; Gonzales, R.A.; Bhattacharyya, MD. J. Biol. Chem. 1996, 271, 9384-9389;
13. (c) Bouvier-Nave, P.; Husseltein, T.; Desprez, T.; Benveniste, P. Eur. J. Biochem. 1997, 246, 518-529;
14. (d) Grebenok, R. J.; Gailbraith, D.W.; Penna, D.D. Plant Mole. Biol. 1997, 34, 891-896.
15. 5. Nes, W.D., McCourt, B.S.; Zhou, W-x, Ma, J., Marshall, J.A.; Peek, L-A.; Brennan, M. Arch. Biochem. Biophys. 1998, 353, 297-311.
16. 6. Nicotra, F.; Ronchetti, F.; Russo, G. J. Labelled Compds. Radiopharmaceuticals 1978, 14, 541-548.
17. 7. Corey, EJ.; Fuchs, P.L. Tetrahedron Lett. 1972, 36, 3169-3772.
18. 13C NMR (75 MHz) Relevant signals are as follows. C8 (123), C9 (140.9), C14 (151.0), C15 (117.3), C23 (25.2), C24 (140.4), C25 (116.4), C26 (87.0), C26′(73.3), C27 (16.9).
19. 9. Le, P.H.; Nes, W.D. Chem. Physics Lipids 1986, 40, 57-69.
20. 10. The financial support of the Welch Foundation (D-1276) and Texas THECB-Advanced Technology Program is gratefully acknowledged.