Disaccharide analogs as probes for glycosyltransferases in Mycobacterium tuberculosis

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 16, 2007, Pages 5629-5650

  Pathak, Ashish K ^a   Pathak, Vibha ^a   Seitz, Lainne ^a   Gurcha, Sudagar S ^b   Besra, Gurdyal S ^b   Riordan, James M ^a   Reynolds, Robert C ^a  

^a SOUTHERN RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Arabinofuranose; Arabinosyltransferases; Fluorescent probe; Galactofuranose; Galactosyltransferases; Glycosyltransferases; Photoaffinity probe; Tuberculosis

Indexed keywords

DANSYL CHLORIDE; DISACCHARIDE; GALACTOSYLTRANSFERASE; GLYCOSYLTRANSFERASE;

ARTICLE; BINDING SITE; BIOASSAY; ISOTOPE LABELING; KINETICS; MOLECULAR PROBE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PHOTOAFFINITY LABELING; SCREENING TEST; SYNTHESIS;

CATALYSIS; DISACCHARIDES; GALACTANS; GLYCOSYLATION; GLYCOSYLTRANSFERASES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; OXIDATION-REDUCTION; PHOTOCHEMISTRY;

CORYNEBACTERINEAE; MYCOBACTERIUM TUBERCULOSIS;

EID: 34250783317     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.04.012     Document Type: Article

References (50)

1. Rattan A., Kalia A., and Ahmad N. Emerging Infect. Dis. 4 (1998) 195-209
2. Butler D. Nature 406 (2000) 670-672
3. Raviglione M.C., Snider D.E., and Kochi A. JAMA 273 (1995) 220-226
4. NIAID, Web Site, http://www.niaid.nih.gov/factsheets/tb.htm; http://www.niaid.nih.gov/factsheets/tbrsch.htm and http://www.who.int/gtb/publications/factsheet/index.htm.
5. Van Scoy R.E., and Wilkowske C.J. Mayo Clin. Proc. 74 (1999) 1038-1048
6. Ravilione M.C. Scot. Med. J. 45 (2000) 52-55
7. Long R. CMAJ 163 (2000) 425-428
8. Walsh C. Nature 406 (2000) 775-781
9. Smith M.B., Boyaromatics M.C., Veasey S., and Woods G.L. Aromaticch. Pathol. Lab. Med. 124 (2000) 1267-1274
10. Pozniak A. Int. J. Tuberc. Lung Dis. 4 (2000) 993-994
11. De Jong B.C., Israelski D.M., Corbett E.L., and Small P.M. Annu. Rev. Med. 55 (2004) 283-301
12. Sibille Y., and Reynolds H. Am. Rev. Respir. Dis. 141 (1990) 47-50
13. Mauch H. Zentralblzhyg Umweltmed. 194 (1993) 152-161
14. Bass J.B., Farer I.S., Hopewell P.C., Obrien R., Jacobs R.F., Ruben F., Snider D.E., and Thornton G. Am. J. Respir. Crit. Care Med. 149 (1994) 1359-1371
15. Blanchard J.S. Annu. Rev. Biochem. 65 (1996) 215-239
16. Lowary T.L. Mycobacterial Cell Wall Components. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology (2001), Springer, Berlin 2005-2080
17. Abou-Zeid C., Voiland A., Michel G., and Cocito C. Eur. J. Biochem. 128 (1982) 363-370
18. Daffe M., Brennan P.J., and McNeil M. J. Biol. Chem. 265 (1990) 6734-6743
19. Brennen P.J., and Nikaido H. Annu. Rev. Biochem. 64 (1995) 29-63
20. Besra G.S., Khoo K.-H., McNeil M.R., Dell A., Morris H.R., and Brennan P. Biochemistry 34 (1995) 4257-4266
21. Lee R.E., Brennan P.J., and Besra G.S. Curr. Top. Microbiol. Immunol. 215 (1996) 1-27
22. Mikusova K., Yagi T., Stern R., McNeil M.R., Besra G.S., Crick D.C., and Brennan P.J. J. Biol. Chem. 275 (2000) 33890
23. Mikusova K., Beláňová M., Korduláková J., Honda K., McNeil M.R., Mahapatra S., Crick D.C., and Brennan P.J.J. Bacteriology 188 (2006) 6592-6598
24. Pathak A.K., Besra G.S., Crick D., Maddry J.A., Morehouse C.B., Suling W.J., and Reynolds R.C. Bioorg. Med. Chem. 7 (1999) 2407-2413
25. Reynolds R.C., Bansal N., Rose J., Friedrich J., Suiling W.J., and Maddry J.A. Carbohydr. Res. 317 (1999) 164-179
26. Pathak A.K., Pathak V., Maddry J.A., Suling W.J., Gurcha S.S., Besra G.S., and Reynolds R.C. Bioorg. Med. Chem. 9 (2001) 3145-3151
27. Pathak A.K., Pathak V., Seitz L., Maddry J.A., Gurcha S.S., Besra G.S., Suling W.J., and Reynolds R.C. Bioorg. Med. Chem. 9 (2001) 3129-3143
28. Pathak A.K., Pathak V., Suling W.J., Gurcha S.S., Morehouse C.B., Besra G.S., Maddry J.A., and Reynolds R.C. Bioorg. Med. Chem. 10 (2002) 923-928
29. Pathak A.K., Pathak V., Kulshrestha M., Kinnaird D., Suling W.J., Gurcha S.S., Besra G.S., and Reynolds R.C. Tetrahedron 59 (2003) 10239-10248
30. Kremer L., Dover L.G., Gurcha S.S., Pathak A.K., Reynolds R.C., and Besra G.S. Carbohydr. Bioeng. (2002) 178-185
31. Bayley H., and Knowles J.R. Methods Enzymol. 46 (1977) 69-114
32. Hazum E. Methods Enzymol. 103 (1983) 58-71
33. Eberle A.N., and deGraan P.N.E. Methods Enzymol. 109 (1985) 129-156
34. Cory P.P., Becker R.R., Rosenbluth R., and Isenberg I. J. Am. Chem. Soc. (1968) 1643-1647
35. Muramoto K., and Kamiya H. Agric. Biol. Chem. 48 (1984) 2695-2699
36. Muramoto K., and Kamiya H. Agric. Biol. Chem. 52 (1988) 547-554
37. Pathak A.K., Pathak V., Bansal N., Maddry J.A., and Reynolds R.C. Tetrahedron Lett. 42 (2001) 979-982
38. Pathak A.K., Pathak V., Gurcha S.S., Besra G.S., and Reynolds R.C. Bioorg. Med. Chem. Lett. 12 (2002) 2749-2752
39. Pathak A.K., Pathak V., Riordan J.M., Gurcha S.S., Besra G.S., and Reynolds R.C. Carbohydr. Res. 339 (2004) 683-691
40. Guthrie R.D., and Smith S.C. Chem. Ind. (London) (1968) 547-548
41. Kam B.L., Barascut J.-L., and Imbach J.-L. Carbohydr. Res. 69 (1979) 135-142
42. Pathak A.K., El-Kattan Y.A., Bansal N., Maddry J.A., and Reynolds R.C. Tetrahedron Lett. 39 (1998) 1497-1500
43. Pathak A.K., Pathak V., Khare N.K., Maddry J.A., and Reynolds R.C. Carbohydr. Lett. 4 (2001) 117-122
44. D'Souza F.W., Cheshev P.E., Ayers J.D., and Lowary T.L. J. Org. Chem. 63 (1998) 9037-9044
45. Chittenden G.J.F. Carbohydr. Res. 25 (1972) 35-41
46. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley 86-91
47. Mizutani K., Kasai R., Nakamura M., Tanaka O., and Matsuura H. Carbohydr. Res. 185 (1989) 27-38
48. Cyr N., and Perlin A.S. Can. J. Chem. 57 (1979) 2504-2511
49. Lee R.E., Brennan P.J., and Besra G.S. Glycobiology 7 (1997) 1121-1128
50. 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