Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-D- erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3465-3469

  Burgos, Emmanuel ^a   Salmon, Laurent ^a  

^a CNRS   (France)

Author keywords

Enzyme inhibitor; Phosphonate; Ribose 5 phosphate isomerase

Indexed keywords

4 DEOXY 4 PHOSPHO DEXTRO ERYTHRONATE; 4 DEOXY 4 PHOSPHONOMETHYL DEXTRO ERYTHRONATE; ARABINOSE DERIVATIVE; ERYTHRONOLIDE DERIVATIVE; ISOENZYME; ISOMERASE INHIBITOR; RIBOSE 5 PHOSPHATE; RIBULOSE PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; HYDROLYSIS; ISOMERIZATION; KINETICS;

EID: 1842637289     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.004     Document Type: Article

References (36)

1. Woodruff W.W., Wolfenden R. J. Biol. Chem. 254:1979;5866-5867.
2. Burgos E., Salmon L. Tetrahedron Lett. 45:2004;753-756.
3. Engel R. Chem. Rev. 77:1977;349-367.
4. Wiemer D.F. Tetrahedron. 53:1997;16609-16644.
5. Le Camus C., Badet-Denisot M.-A., Badet B. Tetrahedron Lett. 39:1998;2571-2572.
6. Arth H.-L., Fessner W.-D. Carbohydr. Res. 305:1998;313-321.
7. Hanessian S., Rogel O. J. Org. Chem. 65:2000;2667-2674.
8. Berkowitz D.B., Bose M., Pfannenstiel T.J., Doukov T. J. Org. Chem. 65:2000;4498-4508.
9. Pasti C., Rinaldi E., Cervellati C., Dallocchio F., Hardré R., Salmon L., Hanau S. Bioorg. Med. Chem. 11:2003;1207-1214.
10. Hirsch G., Grosdemange-Billiard C., Trisch D., Rohmer M. Tetrahedron Lett. 45:2004;519-521.
11. Guanti G., Banfi L., Zannetti M.T. Tetrahedron Lett. 41:2000;3181-3185.
12. Dardonville C., Rinaldi E., Hanau S., Barrett M.P., Brun R., Gilbert I.H. Bioorg. Med. Chem. 11:2003;31-42.
13. Le Camus C., Chassagne A., Badet-Denisot M.-A., Badet B. Tetrahedron Lett. 39:1998;287-288.
14. Le Camus, C. Ph.D. Thesis, Université René Descartes, Paris (France), 1998.
15. Unger F.M., Stix D., Möderndorfer E., Hammerschmid F. Carbohydr. Res. 67:1978;349-356.
16. Zinner H., Braudner H., Reubarz G. Chem. Ber. 3:1956;800-813.
17. Green J.W., Pacsu E. J. Am. Chem. Soc. 59:1937;1205-1210.
18. Haehr H., Smallheer J. Carbohydr. Res. 62:1978;178-184.
19. Kirk K.L. J. Heterocycl. Chem. 22:1985;57-59.
20. Pfitzner K.E., Moffatt J.G. J. Am. Chem. Soc. 1937;5661-5678.
21. a).
22. Le Maréchal P., Froussios C., Level M., Azerad R. Carbohydr. Res. 94:1981;1-10.
23. 3OD) δ=26.3.
24. β ).
25. Chirgwin J.N., Noltmann E. A. J. Biol. Chem. 250:1975;7272-7276.
26. Hardré R., Bonnette C., Salmon L., Gaudemer A. Bioorg. Med. Chem. Lett. 8:1998;3435-3438.
27. Hendriks H.E.J., Kuster B.F.M., Marin G.B. Carbohydr. Res. 214:1991;71-85.
28. El-Subbagh H.I., Racha S., Abushanab E., Panzica R.P. J. Org. Chem. 61:1996;890-894.
29. +) 279.0610, found 279.0608.
30. +) 249.0504, found 249.0506.
31. 2O) δ=28.9.
32. 2O) δ=27.7.
33. Knowles F.C., Pon M.K., Pon N.G. Anal. Biochem. 29:1969;40-47.
34. Nosoh Y., Sekiguchi T. Protein Stability and Stabilization through Protein Engineering. 1991;Ellis Horwood, New York, London, Sydney, Tokyo, Singapore. p 86.
35. Sengmany, S. Ph.D. Thesis, Université Paris-Sud XI, Orsay (France), 2003.
36. Badet, B.; Guénard, D.; Badet-Denisot, M.-A.; Sengmany, S. International Burgenstock Symposium 'Fluorine in Life Sciences', Burgenstock (Switzerland), July 2003.