Synthesis of geranyl S-thiolodiphosphate. A new alternative substrate/inhibitor for prenyltransferases

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2287-2289

  Phan, Richard M ^a   Poulter, C Dale ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLALLYLTRANSFERASE; ENZYME INHIBITOR; GERANYLTRANSFERASE; MONOTHIOPYROPHOSPHORIC ACID; PHOSPHOROTHIOIC ACID DERIVATIVE; PYROPHOSPHATE; TRANSFERASE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; SYNTHESIS;

ALKYL AND ARYL TRANSFERASES; DIMETHYLALLYLTRANSTRANSFERASE; DIPHOSPHATES; ENZYME INHIBITORS; GERANYLTRANSTRANSFERASE; ORGANOTHIOPHOSPHORUS COMPOUNDS;

EID: 0034720921     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006055n     Document Type: Article

References (34)

1. (a) Poulter, C. D.; Rilling, H. C. Acc. Chem. Res. 1978, 11, 307-313.
2. (b) Poulter, C. D.; Mash, E. A.; Argyle, J. C.; Muscio, O. J.; Rilling, H. C. J. Am. Chem. Soc. 1979, 101, 6761-6763.
3. (c) Poulter, C. D.: Rilling, H. C. In Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds.; John Wiley and Sons: New York, 1981; pp 162-224.
4. Ashby, M. N.; Edwards, P. A. J. Biol. Chem. 1990, 265, 13157-13164.
5. Caillet, J.; Droogmans, L. J. Bacteriol. 1988, 170, 4147-4152.
6. Mayer, M. P.; Prestwich, G. D.; Dolence, J. M.; Bond, P. D.; Wu, H.; Poulter, C. D. Gene 1993, 132, 41-47.
7. Tarshis, L. C.; Yan, M.; Poulter, C. D.; Sacchettini, J. C. Biochemistry 1994, 33, 10871-10877.
8. (a) Rilling, H. C.; Block, K. J. Biol. Chem. 1959, 29, 311-314.
9. (b) Conforth, J. W. Angew. Chem., Int. Ed. Engl. 1968, 7, 903-911.
10. (c) Lynen, F.; Eggerer, H.; Henning, U.; Kessel, I. Angew. Chem. 1958, 70, 738-742.
11. (d) Poulter, C. D.; Argyle, J. C.; Mash, E. A. J. Am. Chem. Soc. 1977, 99, 957-959.
12. (a) Corey, E. J.; Volante, R. R. J. Am. Chem. Soc. 1976, 98, 1291-1293.
13. (b) Cane, D. E.; Yang, G.; Xue, Q.; Shim, J. H. Biochemistry 1995, 34, 2471-2479.
14. McClard, R. W.; Fujita, T. S.; Stremler, K. E.; Poulter, C. D. J. Am. Chem. Soc. 1987, 109, 5544-5545.
15. Stremler, K. E.; Poulter, C. D. J. Am. Chem. Soc. 1987, 109, 5542-5544.
16. (a) Blackburn, G. M.; England, D. A.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 930-932.
17. (b) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Chem. Commun. 1981, 1188-1190.
18. (c) Blackburn, G. M.; Eckstein, F.; Kent, D. E.; Perree, T. D. Nucleosides Nucleotides 1985, 4, 165-167.
19. (a) Goody, R. S.; Eckstein, F. J. Am. Chem. Soc. 1971, 93, 6252.
20. (b) Burgers, B. M. J.; Ecksteinm F. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 4798-4800.
21. (c) Richard, J. P.; Frey, P. A. J. Am. Chem. Soc. 1982, 104, 3476-3481.
22. (d) Eckstein, F. Annu. Rev. Biochem. 1985, 54, 367-402.
23. (e) Gish, G.; Eckstein, F. TIBS 1989, 14, 97-100.
24. (g) Eckstein, F.; Ludwig, J. J. Org. Chem. 1991, 56, 1777-1783.
25. Poulter, C. D.; Mautz, D. S. J. Am,. Chem. Soc. 1991, 113, 4895-4903.
26. (a) Davisson, V. J.; Woodside, A. B.; Poulter, C. D. Method Enzymol. 1984, 110, 130-144.
27. (b) Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Poulter, C. D. J. Org. Chem. 1986, 51, 4768-4778.
28. (a) Chojnowski, J.; Cypryk, M.; Fortuniak, W.: Michalski, J. Synth. Commun. 1977, 683-686.
29. (b) Almasi, L. In Sulfur in Organic and Inorganic Chemistry; Senning, A., Ed.; Marcel Dekker: New York, 1971.
30. (a) Blackburn, G. M.; Ingleson, K. J. Chem. Soc., Chem. Commun. 1978, 870-871.
31. (b) Zygmunt, J.; Kafarski, P.; Mastalerz, P. Synthesis 1978, 609.
32. Reed, B. C.; Rilling, H. C. Biochemistry 1975, 14, 50-54.
33. The acid-lability assay is described in the Supporting Information.
34. The reaction mixture was prepared in the same manner as the assay mixture for the acid-lability assay.