Synthesis and biological evaluation of new inhibitors of UDP-Galftransferase - A key enzyme in M. tuberculosis cell wall biosynthesis

Organic and Biomolecular Chemistry

Volumn 2, Issue 17, 2004, Pages 2418-2420

  Cren, Sylvaine ^a   Gurcha, Sudagar S ^b   Blake, Alexander J ^a   Besra, Gurdyal S ^b   Thomas, Neil R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BIOSYNTHESIS; CATALYSIS; CELLS; DNA; METABOLISM; STEREOCHEMISTRY; SUGARS;

CELL WALL; PROTONATION; RING CLOSING METATHESIS (RCM); TRANSFERASE REACTIONS;

ENZYME INHIBITION;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

ENZYME INHIBITOR; GALACTAN; GALACTOSYLTRANSFERASE; IMINE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; CELL WALL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; ENZYME SPECIFICITY; ENZYMOLOGY; METABOLISM; MICROBIOLOGICAL EXAMINATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CATALYSIS; CELL WALL; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; GALACTANS; GALACTOSYLTRANSFERASES; IMINES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 4744341919     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/B411554f     Document Type: Article

References (26)

1. World Health Organisation: http://www.who.int/mediacentre/factsheets/ fs104/en/.
2. F. Pan, M. Jackson, Y. Ma and M. McNeil, J. Bacterial., 2001, 183, 3991.
3. M.Daffe, P. J. Brennan and M. McNeil, J. Biol. Chem., 1990, 265, 6734.
4. D. A. R. Sanders, A. G. Staines, S. A. McMahon, M. R. McNeil, C. Whitfield and J. H. Naismith, Nat. Struct. Biol., 2001, 8, 858.
5. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
6. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
7. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
8. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
9. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
10. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
11. The mechanism of the interconversion UDP-Galp/UDP-Galf remains unclear, for discussions, see: (a) J. N. Barlow, M. E. Girvin and J. S. Blanchard, J. Am. Chem. Soc., 1999, 121, 6968; (b) Q. Zhang and H.W.Liu, J. Am. Chem. Soc., 2000, 122, 9065; S. W. B. Fullerton, S.Daff, D. A. R. Sanders, W. J. Ingledew, C. Whitfield, S. K. Chapman and J. H. Naismith, Biochemistry, 2003, 42, 2104; Z. Huang, Q. Zhang and H. W. Liu, Bioorg. Chem., 2003, 31, 494; (e) A. Caravano, D. Mengin-Lecreulx, J. M. Brondello, S. P. Vincent and P. Sinaÿ, Chem. Eur. J., 2003, 9, 5888; (f) M. Soltero-Higgin, E. E. Carlson, T. D. Gruber and L. L. Kiessling, Nat. Struct. Mol. Biol., 2004, 11, 539; (g) A. Caravane, S. P. Vincent and P. Sinay, Chem. Commun., 2004, 1216.
12. L. Kremer, L. G. Dover, C. Morehouse, P. Hitchin, M. Everett, H. R. Morris, A. Dell, P. J. Brennan, M. R. McNeil, C. Flaherty, K. Duncan and G. S. Besra, J. Biol. Chem., 2001, 276, 26430.
13. (a) A. E. Stütz, Iminosugars as glycosidase inhibitors: Nojirimydn and beyond, Wiley-VCH, Weinheim, 1999;
14. V. H. Lillelund, H. H. Jensen, X. Liang and M. Bols, Chem. Rev., 2002, 102, 515.
15. R. E. Lee, M. D. Smith, R. J. Nash, R. C. Griffiths, M. McNeil, R. K. Grewal, W. X. Yan, G. S. Besra, P. J. Brennan and G. W. J. Fleet, Tetrahedron Lett., 1997, 38, 6733.
16. S.U.Hansen and M.Bols, Acta Chem. Scand., 1998, 52, 1214.
17. (a) V. V. Filichev, M. Brandt and E. B. Pedersen, Carbohydr. Res., 2001, 333, 115;
18. (b) V. V. Filichev and E. B. Pedersen, Org. Biomol. Chem., 2003, 1, 100.
19. C. Look, C. H. Fotsch arid C.-H. Wong, Acc. Chem. Res., 1993, 26, 182.
20. R. Stürmer, Synthesis, 2001, 46.
21. A.K.Pathak, V.Pathak, L. Seitz, J. A. Maddry, S.S.Gurcha,G. S.Besra, W. J. Suling and R. C. Reynolds, Bioorg. Med. Chem., 2001, 9, 3129.
22. Calculated using GraFit version 4.0, R. J. Leatherbarrow, Erithacus Software Ltd, Staines, UK.
23. P. Compain and O. R. Martin, Curr. Top. Med. Chem., 2003, 3, 541; P. Compain and O. R. Martin, Bioorg. Med. Chem., 2001, 9, 3077.
24. P. Compain and O. R. Martin, Curr. Top. Med. Chem., 2003, 3, 541; P. Compain and O. R. Martin, Bioorg. Med. Chem., 2001, 9, 3077.
25. M. S. Scherman, K. A. Winans, R. J. Stern, V. Jones, C. R. Bertozzi and M. R. McNeil, Antimicrob. Agents Chemother., 2003, 47, 378.
26. C. J. Halfman, Methods Enzympl., 1981, 74, 481.