Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU

Carbohydrate Research

Volumn 346, Issue 13, 2011, Pages 1714-1720

  Li, Yongmeng ^a,b   Zhou, Yan ^c   Mac, Yufang ^c   Li, Xuebing ^a  

^a INSTITUTE OF MICROBIOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c DALIAN MEDICAL UNIVERSITY   (China)

Author keywords

Analog; GlmM; GlmU; Glucosamine 1 phosphate; Glucosamine 6 phosphate; Mycobacterium tuberculosis

Indexed keywords

BIOCHEMISTRY; ENZYMES;

ANALOG; BIFUNCTIONAL ENZYMES; GLMM; GLMU; MYCOBACTERIAL CELLS; MYCOBACTERIUM TUBERCULOSIS; N-ACETYL-D-GLUCOSAMINE; URIDINE TRIPHOSPHATE;

GLUCOSAMINE;

2 AMINO 2,3 DIDEOXY 3 FLUORO ALPHA DEXTRO GLUCOPYRANOSYL PHOSPHATE; 2 AZIDO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL PHOSPHATE; ENZYME; GLMM ENZYME; GLMU ENZYME; GLUCOSAMINE 1 PHOSPHATE; GLUCOSAMINE 6 PHOSPHATE; METHYL 2 AMINO 2 DEOXYL ALPHA DEXTRO GLUCOPYRANOSIDE 6 PHOSPHATE; METHYL 2 AMINO 2 DEOXYL BETA DEXTRO GLUCOPYRANOSIDE 6 PHOSPHATE; N ACETYLGLUCOSAMINE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL WALL; DRUG SYNTHESIS; HUMAN; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL;

MYCOBACTERIUM TUBERCULOSIS;

EID: 80053567773     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2011.05.024     Document Type: Article

References (29)

1. Dye, C.; Scheele, S.; Dolin, P.; Pathania, V.; Raviglione, M. C. JAMA 1999, 282, 677-686
2. O'Brien, R. J.; Nunn, P. P. T. Am. J. Respir. Crit. Care Med. 2001, 163, 1055-1058
3. Ginsberg, A. M.; Spigelman, M. Nat. Med. 2007, 13, 290-294
4. McNeil, M. R.; Brennan, P. Res. Microbiol. 1991, 142, 451-463
5. Mengin, L. D.; Van Heijenoort, J. J. Biol. Chem. 1996, 32, 271-273
6. Zhang, W. L.; McNeil, M. R.; Ma, Y. F. Int. J. Biochem. Cell Biol. 2008, 40, 2560-2571.
7. Barry, C. E.; Crick, D. C.; McNeil, M. R. Infect. Disord. Drug Targets 2007, 7, 182-202.
8. Lim, J.; Grove, B. C.; Roth, A.; Breaker, R. R. Angew. Chem., Int. Ed. 2006, 45, 6689-6693
9. Feng, F.; Okuyama, K.; Niikura, K.; Ohta, T.; Sadamoto, R.; Monde, K.; Noguchi, T.; Nishimura, S. I. Org. Biomol. Chem. 2004, 2, 1617-1623
10. Hartman, M. C. T.; Coward, J. K. J. Am. Chem. Soc. 2002, 124, 10036-10053
11. Hayashi, T.; Murray, B. W.; Wang, R.; Wong, C. H. Bioorg. Med. Chem. 1997, 5, 497-500
12. Ohno, N.; Yui, S.; Yadoma, T.; Miyazaki, T. Carbohydr. Res. 1981, 90, 334-338
13. Yan, R. B.; Yang, F.; Wu, Y. F.; Zhang, L. H.; Ye, X. S. Tetrahedron Lett. 2005, 46, 8993-8995
14. Zhou, Y.; Lin, F.; Chen, J. F.; Yu, B. Carbohydr. Res. 2006, 341, 1619-1629
15. Szabó, P. J. Chem. Soc., Perkin Trans. 1 1989, 919-924
16. Sala, R. F.; MacKinnon, S. L.; Palcic, M. M.; Tanner, M. E. Carbohydr. Res. 1998, 306, 127-136
17. Minuth, T.; Irmak, M.; Groschner, A.; Lehnert, T.; Boysen, M. M. K. Eur. J. Org. Chem. 2009, 997-1008
18. Buskas, T.; Garegg, P. J.; Konradsson, P.; Maloisel, J. L. Tetrahedron: Asymmetry 1994, 5, 2187-2194
19. Gregg, P. J.; Kotuadsson, P.; Oscarson, S.; Ruda, K. Tetrahedron 1997, 53, 17721-17734.
20. Luo, S. Y.; Thopate, S. R.; Hsu, C. Y.; Hung, S. C. Tetrahedron Lett. 2002, 43, 4889-4892.
21. Card, P. J. J. Org. Chem. 1983, 48, 393-395
22. Kajihara, Y.; Kodama, H.; Endo, T.; Hashimoto, H. Carbohydr. Res. 1998, 306, 361-378
23. Bos, L. J.; Boltje, T. J.; Provoost, T.; Mazurek, J.; Overkleeft, H. S.; Marel, G. A. Tetrahedron Lett. 2007, 48, 2697-2700
24. Hansson, J.; Garegg, P. J.; Oscarson, S. J. Org. Chem. 2001, 66, 6234-6243
25. Muller, T.; Danac, R.; Ball, L.; Gurr, S. J.; Fairbanks, A. J. Tetrahedron: Asymmetry 2007, 18, 1299-1307
26. Chang, R.; Moquist, P.; Finney, N. S. Carbohydr. Res. 2004, 339, 1531-1536
27. Ellman, G. L. Arch. Biochem. Biophys. 1958, 74, 443-450
28. Nicholas, G. M.; Eckman, L. L.; Newton, G. L.; Fahey, R. C.; Ray, S.; Bewley, C. A. Bioorg. Med. Chem. 2003, 11, 601-608
29. Pereira, M. P.; Blanchard, J. E.; Murphy, C.; Roderick, S. L.; Brown, E. D. Antimicrob. Agents Chemother. 2009, 53, 2306-2311.