Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 19, 2007, Pages 6443-6449

  Desvergnes, Stéphanie ^a   Desvergnes, Valérie ^b   Martin, Olivier R ^b   Itoh, Kenji ^c   Liu, Hung wen ^c   Py, Sandrine ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c The Center for Molecular Carcinogenesis and Toxicology   (United States)

Author keywords

Arabinogalactan; Enzyme inhibition; Galactofuranose; Iminogalactitols; Iminosugars; Mycobacterium; Nitrone; Pyrrolidines; Pyrrolizidines; Reductive coupling; Samarium diiodide; Tuberculosis; UDP galactose mutase; Umpolung

Indexed keywords

1,4 DIDEOXY 1,4 IMINO DEXTRO GALACTITOL; 3 [3,4 DIHYDROXY 5 (1,2 DIHYDROXYETHYL)PYRROLIDIN 2 YL]PROPANOIC ACID; 3 [3,4 DIHYDROXY 5 (1,2 DIHYDROXYETHYL)PYRROLIDIN 2 YL]PROPIONIC ACID ETHYL ESTER; BICYCLO COMPOUND; CARBON; GALACTITOL; HEXAHYDRO 3 (1,2 DIHYDROXYETHYL) 1H PYRROLIZINE 1,2 DIOL; HEXAHYDRO 6,7 DIHYDROXY 5 (1,2 DIHYDROXYETHYL)PYRROLIDIN 3 ONE; ISOMERASE INHIBITOR; MUTASE; NITRONE; PYRROLIDINE DERIVATIVE; SAMARIUM; SAMARIUM IODIDE; UDP GALACTOPYRANOSE MUTASE; UDP GALACTOPYRANOSE MUTASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

BICYCLO COMPOUNDS; ENZYME INHIBITORS; ESCHERICHIA COLI; GALACTITOL; INTRAMOLECULAR TRANSFERASES; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

ESCHERICHIA COLI; MYCOBACTERIUM;

EID: 34547762178     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.06.059     Document Type: Article

References (53)

1. Jarlier V., and Nikaido H. FEMS Microbiol. Lett. 123 (1994) 11-18
2. Nguyen L., and Thompson C.J. Trends Microbiol. 7 (2006) 304-312
3. O'Brien R.J., and Nunn P.P. Am. J. Respir. Crit. Care Med. 163 (2001) 1055-1058
4. Zhang Y., and Amzel L.M. Curr. Drug Targets 3 (2002) 131-154
5. See for example:. Takayama K., and Kilburn J.O. Antimicrob. Agents Chemother. 33 (1989) 1493-1499
6. Wen X., Crick D.C., Brennan P.J., and Hultin P.G. Bioorg. Med. Chem. 17 (2003) 3579-3587
7. Gobec S., Plantan I., Mravljak J., Švajger U., Wilson R.A., Besra G.S., Soares S.L., Appelberg R., and Kikelj D. Eur. J. Med. Chem. (2006) 1-10
8. Rastogi N., Goh K.S., and David H.L. Antimicrob. Agents Chemother. 34 (1990) 759-764
9. Barry C.E. Biochem. Pharmacol. 54 (1997) 1165-1172
10. Pan F., Jackson M., Ma Y., and McNeil M.R. J. Bacteriol. 183 (2001) 3991-3998
11. Pedersen L.L., and Turco S.J. Cell. Mol. Life Sci. 60 (2003) 259-266
12. Cren S., Gurcha S.S., Blake A.J., Besra G.S., and Thomas N.S. Org. Biomol. Chem. 2 (2004) 2418-2420
13. Rose N.L., Completo G.C., Lin S.-J., McNeil M., Palcic M.M., and Lowary T.L. J. Am. Chem. Soc. 128 (2006) 6721-6729
14. Mikusova K., Belanova M., Kordulakova J., Honda K., McNeil M.R., Mahapatra S., Crick D.C., and Brennan P.J. J. Bacteriol. 188 (2006) 6592-6598
15. Wing C., Errey J.C., Mukhopadhyay B., Blanchard J.S., and Field R.A. Org. Biomol. Chem. 4 (2006) 3945-3950
16. Kremer L., Dover L.G., Morehouse C., Hitchin P., Everett M., Morris H.R., Dell A., Brennan P.J., McNeil M.R., Flaherty C., Duncan K., and Besra G.S. J. Biol. Chem. 276 (2001) 26430-26440
17. Escherichia coli UGM:. Sanders D.A.R., Staines A.G., McMahon S.A., McNeil M., Whitfield C., and Naismith J.H. Nat. Struct. Biol. 8 (2001) 858-863
18. Mycobacterium tuberculosis UGM:. Beis K., Srikannathasan V., Liu H., Fullerton S.W.B., Bamford V.A., Sanders D.A.R., Whitfield C., McNeil M.R., and Naismith J.H. J. Mol. Biol. 348 (2005) 971-982
19. Barlow J.N., Girvin M.E., and Blanchard J.S. J. Am. Chem. Soc. 121 (1999) 6968-6969
20. Zhang Q., and Liu H.-w. J. Am. Chem. Soc. 122 (2000) 9065-9070
21. Zhang Q., and Liu H.-w. J. Am. Chem. Soc. 123 (2001) 6756-6766
22. Fullerton S.W.B., Daff S., Sanders D.A.R., Ingledew W.J., Whitfield C., Chapman S.K., and Naismith J.H. Biochemistry 42 (2003) 2104-2109
23. Soltero-Higgin M., Carlson E.E., Gruber T.D., and Kiessling L.L. Nat. Struct. Mol. Biol. 11 (2004) 539-543
24. Miller S.M. Nat. Struct. Mol. Biol. 11 (2004) 497-498
25. Lee R.E., Smith M.D., Nash R.J., Griffiths R.C., McNeil M., Grewal R.K., Yan W., Besra G.S., Brennan P.J., and Fleet G.W.J. Tetrahedron Lett. 38 (1997) 6733-6736
26. Lee R.E., Smith M.D., Pickering L., and Fleet G.W.J. Tetrahedron Lett. 40 (1999) 8689-8692
27. Veerapen N., Yu Y., Sanders D.A.R., and Pinto B.M. Carbohydr. Res. 339 (2004) 2205-2217
28. Liautard V., Desvergnes V., and Martin O.R. Org. Lett. 8 (2006) 1299-1302
29. Liautard V., Christina A.E., Desvergnes V., and Martin O.R. J. Org. Chem. 71 (2006) 7337-7345
30. Caravano A., Mengin-Lecreulx D., Brondello J.-M., Vincent S.P., and Sinaÿ P. Chem. Eur. J. 9 (2003) 5888-5898
31. Caravano A., Vincent S.P., and Sinaÿ P. Chem. Commun. (2004) 1216-1217
32. Sadeghi-Khomani A., Blake A.J., Wilson C., and Thomas N.R. Org. Lett. 7 (2005) 4891-4894
33. Caravano A., Dohi H., Sinaÿ P., and Vincent S.P. Chem. Eur. J. 12 (2006) 3114-3123
34. Huang Z., Zhang Q., and Liu H.-w. Bioorg. Chem. 31 (2003) 494-502
35. Caravano A., Vincent S.P., and Sinaÿ P. Bioorg. Med. Chem. Lett. 16 (2006) 1123-1125
36. Itoh K., Huang Z., and Liu H.-w. Org. Lett 9 (2007) 879-882
37. Stütz A.E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (1999), Wiley-VCH, Weinheim
38. Compain P., and Martin O.R. Curr. Top. Med. Chem. 3 (2003) 541-560
39. Masson G., Py S., and Vallée Y. Angew. Chem., Int. Ed. 41 (2002) 1772-1775
40. Masson G., Cividino P., Py S., and Vallée Y. Angew. Chem., Int. Ed. 42 (2003) 2265-2268
41. Riber D., and Skrydstrup T. Org. Lett. 5 (2003) 229-231
42. Desvergnes S., Py S., and Vallée Y. J. Org. Chem. 70 (2005) 1459-1462
43. For a recent review on enantiopure cyclic nitrones including carbohydrate-derived nitrones, see:. Revuelta J., Cicchi S., Goti A., and Brandi A. Synthesis (2007) 485-504
44. First use in organic synthesis:. Girard P., Namy J.-L., and Kagan H.B. J. Am. Chem. Soc. 102 (1980) 2693-2698
45. 2 in synthesis:. Molander G.A., and Harris C.R. Chem. Rev. 96 (1996) 307-338
46. Krief A., and Laval A.-M. Chem. Rev. 99 (1999) 745-777
47. Kagan H.B. Tetrahedron 59 (2003) 10351-10372
48. Edmonds D.J., Johnston D., and Procter D.J. Chem. Rev. 104 (2004) 3371-3403
49. 2 in THF:. Curran D.P., Zhang W., and Dowd P. Tetrahedron 53 (1997) 9023-9042
50. Masson G., Zeghida W., Cividino P., Py S., and Vallée Y. Synlett (2003) 1527-1529
51. Lee R., Monsey D., Weston A., Duncan K., Rithner C., and McNeil M. Anal. Biochem. 242 (1996) 1-7
52. Desvergnes, V.; Martin, O.R.; Liu, H.-w. unpublished results.
53. Meynial I., Paquet V., and Combes D. Anal. Chem. 67 (1995) 1627-1631