Nitrogen-containing bisphosphonates as carbocation transition state analogs for isoprenoid biosynthesis

Biochemical and Biophysical Research Communications

Volumn 263, Issue 3, 1999, Pages 754-758

  Martin, Michael B ^a   Arnold, William ^a   Heath III, Huel T ^a   Urbina, Julio A ^a   Oldfield, Eric ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; BISPHOSPHONIC ACID DERIVATIVE; DRUG ANALOG; GERANYLTRANSFERASE; ISOPRENOID; MEVALONIC ACID; NITROGEN; OXYGEN;

ALKYLATION; ARTICLE; BINDING SITE; BIOSYNTHESIS; CALCULATION; MOLECULAR MODEL; PRIORITY JOURNAL;

EID: 0033527417     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1006/bbrc.1999.1404     Document Type: Article

References (24)

1. Rawls R. Chem. Eng. News. 94:1998;38-40.
2. Rodan G. A. Annu. Rev. Pharmacol. Toxicol. 38:1998;375-388.
3. Fisher J. E., Rogers M. J., Halasy J. M., Luckman S. P., Hughes D. E., Masarachia P. J., Wesolowski G., Russell R. G. G., Rodan G. A., Reszka A. A. Proc. Natl. Acad. Sci. USA. 96:1999;133-138.
4. van Beek E., Pieterman E., Cohen L., Lowik C., Papapoulos S. Biochem. Biophys. Res. Commun. 255:1999;491-494.
5. Cromartie T. H., Fisher K. J., Grossman J. N. Pest. Biochem. Physiol. 63:1999;114-126.
6. Oberhauser V., Gaudin J., Fonne-Pfister R., Schar H. P. Pest. Biochem. Physiol. 60:1998;111.
7. Frisch, M. J, Trucks, G. W, Schlegal, H. B, Gill, P. M. W, Johnson, B. G, Robb, M. A, Cheeseman, J. R, Keith, T, Petersson, G. A, Montgomery, J. A, Raghavachari, K, Al-Laham, M. A, Zakrzewski, V. G, Ortiz, J. V, Foresman, J. B, Cioslowski, J, Stefanov, B. B, Nanayakara, A, Challacombe, M, Peng, C. Y, Ayala, P. Y, Chen, W, Wong, M. W, Andres, J. L, Replogle, E. S, Gomperts, R, Martin, R. L, Fox, D. J, Binkley, J. S, Defrees, D. J, Baker, J, Stewart, J. P, Head-Gordon, M, Gonzalez, C, and, Pople, J. A. 1995, Gaussian 94, Revision C.2, Gaussian, Inc. Pittsburgh, PA.
8. Tarshis L. C., Yan M., Poulter C. D., Sacchettini J. C. Biochemistry. 33:1994;10871-10877.
9. 2 Modeling Environment, Version 3.5, 1997, Molecular Simulations Inc. San Diego, 1998.
10. DelPhi Program, 1998, Molecular Simulations Inc. San Diego, 1998.
11. Reardon J. E., Abeles R. H. J. Am. Chem. Soc. 107:1985;4078-4079.
12. Muehlbacher M., Poulter C. D. J. Am. Chem. Soc. 107:1985;8307-8308.
13. Reardon J. E., Abeles R. H. Biochemistry. 25:1986;5609-5616.
14. van Beek E., Lowik C., van der Pluijm G., Papapoulos S. J. Bone Miner. Res. 14:1999;722-729.
15. Muehlbacher M., Poulter C. D. Biochemistry. 27:1988;7315-7328.
16. Tarshis L. C., Proteau P. J., Kellogg B. A., Sacchettini J. C., Poulter C. D. Proc. Natl. Acad. Sci. USA. 93:1996;15018-15023.
17. Bernstein F. C., Koetzle T. F., Williams G. J., Meyer E. E. Jr., Brice M. D., Rodgers J. R., Kennard O., Shimanouchi T., Tasumi M. J. Mol. Biol. 112:1977;535.
18. Benedict, J. J, and, Perkins, C. M. 1995, European Patent Application #85309140.3.
19. Rogers M. J., Ji X., Russell G. G., Blackburn G. M., Williamson M. P., Bayless A. V., Ebetino F. H., Watts D. J. Biochem. J. 303:1994;303-311.
20. Bruchhaus I., Jacobs T., Denart M., Tannich E. Biochem. J. 316:1996;57-63.
21. Sagami H., Korenbaga T., Ogura K., Steiger A., Pyun H.-J., Coates R. M. Arch. Biochem. Biophys. 297:1992;314-329.
22. McClard R. M., Fujita T. S., Stremler K. E., Poulter C. D. J. Am. Chem. Soc. 109:1987;5544-5545.
23. Urbina, J. A, Moreno, B, Vierkotter, S, Oldfield, E, Payares, G, Sanoja, C, Bailey, B. N, Yan, W, Scott, D. A, Moreno, S. J, and, Docampo, R. 1999, Submitted.
24. Rodrigues, C. O, Scott, D. A, Bailey, B, de Souza, W, Benchimol, M, Moreno, B, Urbina, J. A, Oldfield, E, and, Moreno, S. N. J. 1999, Submitted.