Design, Synthesis, and Evaluation of 9-D-Ribitylamino-1,3,7,9-tetrahydro-2,6,8-purinetriones Bearing Alkyl Phosphate and α,α-Difluorophosphonate Substituents As Inhibitors of Riboflavin Synthase and Lumazine Synthase

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 601-612

  Cushman, Mark ^a   Sambaiah, Thota ^a   Jin, Guangyi ^a   Illarionov, Boris ^b   Fischer, Markus ^b   Bacher, Adelbert ^b  

^a PURDUE UNIVERSITY   (United States)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; BIOSYNTHESIS; ELECTRON TRANSPORT PROPERTIES; ESCHERICHIA COLI; METABOLITES; VITAMINS;

METABOLIC STABILITY;

ENZYMES;

3 (1,3,7,9 TETRAHYDRO 9 DEXTRO RIBITYL 2,6,8 TRIOXOPURIN 7 YL)PROPANE 1 PHOSPHATE; 3,4 DIHYDROXYBUTANONE 4 PHOSPHATE; 9 DEXTRO RIBITYLAMINO 1,3,7,9 TETRAHYDRO 2,6,8 PURINETRIONE; ALKYL GROUP; ALPHA,ALPHA DIFLUOROPHOSPHONATE; ANTIBIOTIC AGENT; ENZYME INHIBITOR; LUMAZINE; LUMAZINE SYNTHASE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PURINE DERIVATIVE; RIBOFLAVIN; RIBOFLAVIN SYNTHASE; TROMETAMOL; UNCLASSIFIED DRUG;

ALKYLATION; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BINDING SITE; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME INHIBITION; ENZYME KINETICS; ESCHERICHIA COLI; HYDROGEN BOND; MOLECULAR MODEL; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

BACILLUS SUBTILIS; BINDING, COMPETITIVE; DRUG DESIGN; ENZYME INHIBITORS; ESCHERICHIA COLI; KINETICS; MODELS, MOLECULAR; MULTIENZYME COMPLEXES; PHOSPHONIC ACIDS; PHOSPHORIC ACID ESTERS; PURINES; RECOMBINANT PROTEINS; RIBITOL; RIBOFLAVIN SYNTHASE;

EID: 0842328958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030278k     Document Type: Article

References (33)

1. Plaut, G. W. E.; Smith, C. M.; Alworth, W. L. Annu. Rev. Biochem. 1974, 43, 899-922.
2. Plaut, G. W. E. In Comprehensive Biochemistry; Florkin, M., Stotz, E. H., Eds.; Elsevier: Amsterdam, 1971; Vol. 21, pp 11-45.
3. Beach, R. L.; Plaut, G. W. E. J. Am. Chem. Soc. 1970, 92, 2913-2916.
4. Bacher, A.; Eberhardt, S.; Richter, G. In Escherichia coli and Salmonella: Cellular and Molecular Biology, 2nd ed.; Neidhardt, F. C., Ed.; ASM Press: Washington, DC, 1996; pp 657-664.
5. Bacher, A.; Fischer, M.; Kis, K.; Kugelbrey, K.; Mörtl, S.; Scheuring, J.; Weinkauf, S.; Eberhardt, S.; Schmidt-Bäse, K.; Huber, R.; Ritsert, K.; Cushman, M.; Ladenstein, R. Biochem. Soc. Trans. 1996, 24, 89-94.
6. Volk, R.; Bacher, A. J. Am. Chem. Soc. 1988, 110, 3651-3653.
7. Cushman, M.; Mihalic, J. T.; Kis, K.; Bacher, A. J. Org. Chem. 1999, 64, 3838-3845.
8. Meining, W.; Mörtl, S.; Fischer, M.; Cushman, M.; Bacher, A.; Ladenstein, R. J. Mol. Biol. 2000, 299, 181-197.
9. Zhang, X.; Meining, W.; Cushman, M.; Haase, I.; Fischer, M.; Bacher, A.; Ladenstein, R. J. Mol. Biol. 2003, 328, 167-182.
10. Cushman, M.; Yang, D.; Kis, K.; Bacher, A. J. Org. Chem. 2001,166, 8320-8327.
11. Wang, A. Yichuan Xuebao 1992, 19, 362-368.
12. Oltmanns, O.; Lingens, F. Z. Naturforsch. 1967, 22, 751-754.
13. Logvinenko, E. M.; Shavlovsky, G. M. Mikrobiologiya 1967, 41, 978-979.
14. Neuberger, G.; Bacher, A. Biochem. Biophys. Res. Commun. 1985, 127, 175-181.
15. Nutiu, R.; Boulton, A. J. J. Chem. Soc., Perkin Trans. 1 1976, 1327-1331.
16. Kendall, P. M.; Johnson, J. V.; Cook, C. E. J. Org. Chem. 1979, 44, 1421-1424.
17. Newton, R. F.; Reynolds, D. P.; Webb, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1981, 2055-2058.
18. Ogawa, Y.; Nunomoto, M.; Shibasaki, M. J. Org. Chem. 1986, 51, 1625-1627.
19. Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 549-557.
20. Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron Lett. 1998, 39, 641-6414.
21. Olah, G. A.; Nojima, M.; Kerekes, I. Synthesis 1973, 786-787.
22. Kabachnik, M. I.; Mastrukova, T. A.; Shipov, A. E.; Melentyeva, T. A. Tetrahedron 1960, 9, 10-28.
23. Smyth, M. S.; Ford, H., Jr.; Burke, T. R., Jr. Tetrahedron Lett. 1992, 33, 4137-4140.
24. Halazy, S.; Ehrhard, A.; Danzin, C. J. Am. Chem. Soc. 1991, 113, 315-317.
25. Cushman, M.; Yang, D.; Mihalic, J. T.; Chen, J.; Gerhardt, S.; Huber, R. ; Fischer, M.; Kis, K.; Bacher, A. J. Org. Chem. 2002, 67, 6871-6877.
26. Ritsert, K.; Huber, R.; Turk, D.; Ladenstein, R.; Schmidt-Bäse, K.; Bacher, A. J. Mol. Biol. 1995, 253, 151-167.
27. Gerhardt, S.; Haase, I.; Steinbacher, S.; Kaiser, J. T.; Cushman, M.; Bacher, A.; Huber, R.; Fischer, M. J. Mol. Biol. 2002, 318, 1317-1329.
28. Gerhardt, S.; Schott, A.-K.; Kairies, N.; Cushman, M.; Illarionov, B.; Eisenreich, W.; Bacher, A.; Huber, R.; Steinbacher, S.; Fischer, M. Structure 2002, 10, 1371-1381.
29. Truffault, V.; Coles, M.; Diericks, T.; Abelmann, K.; Eberhardt, S.; Lüttgen, H.; Bacher, A.; Kessler, H. J. Mol. Biol. 2001, 309, 949-960.
30. Liao, D.-I.; Wawrzak, Z.; Calabrese, J. C.; Viitanen, P. V.; Jordan, D. B. Structure 2001, 9, 399-408.
31. Kis, K.; Bacher, A. J. Biol. Chem. 1995, 270, 16788-16795.
32. Kuzmic, P. Anal. Biochem. 1996, 237, 260-273.
33. Eberhardt, S.; Richter, G.; Gimbel, W.; Werner, T.; Bacher, A. Eur. J. Biochem. 1996, 242, 712-718.