Conformational analyses of mycothiol, a critical intracellular glycothiol in Mycobacteria

Carbohydrate Research

Volumn 341, Issue 9, 2006, Pages 1164-1173

  Hand, Christine E ^a   Auzanneau, France Isabelle ^b   Honek, John F ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

^b UNIVERSITY OF GUELPH   (Canada)

Author keywords

Conformational analyses; Glycothiol; Mycobacteria; Mycothiol

Indexed keywords

ALDEHYDES; AMINO ACIDS; BACTERIA; BACTERIOLOGY; BIOCHEMISTRY; FUNGI; HYDROGENATION; MOLECULAR DYNAMICS; STOCHASTIC CONTROL SYSTEMS;

CONFORMATIONAL ANALYSES; GLYCOTHIOLS; MYCOBACTERIA; MYCOTHIOLS;

CONFORMATIONS;

CARBOHYDRATE DERIVATIVE; GLYCOTHIOL; MYCOTHIOL; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBOHYDRATE ANALYSIS; CLUSTER ANALYSIS; COMPARATIVE STUDY; CONFORMATION; ENERGY; FORCE; GAS; MYCOBACTERIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SOLVATION; STATISTICS;

CARBOHYDRATE CONFORMATION; CYSTEINE; DISACCHARIDES; GLYCOPEPTIDES; INOSITOL; INTRACELLULAR FLUID; MYCOBACTERIUM; PYRAZOLES; SULFHYDRYL COMPOUNDS;

ACTINOMYCETALES; CORYNEBACTERINEAE; EUKARYOTA; MYCOBACTERIUM TUBERCULOSIS; STREPTOMYCES;

EID: 33646510833     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.03.020     Document Type: Article

References (56)

1. Hand C.E., and Honek J.F. J. Nat. Prod. 62 (2005) 293-308 and references cited therein
2. Fahey R.C. Annu. Rev. Microbiol. 55 (2001) 333-356 and references cited therein
3. Newton G.L., and Fahey R.C. Meth. Enzymol. 251 (1995) 148-166
4. Newton G.L., and Javor B. J. Bacteriol. 161 (1985) 438-441
5. Fairlamb A.H., Blackburn P., Ulrich P., Chait B.T., and Cerami A. Science 227 (1985) 1485-1487
6. Newton G.L., Arnold K., Price M.S., Sherrill C., Delcardayre S.B., Aharonowitz Y., Cohen G., Davies J., Fahey R.C., and Davis C. J. Bacteriol. 178 (1996) 1990-1995
7. World Health Organization. Tuberculosis: www.who.int/mediacentre/factsheets/fs104/en/print.html.
8. Food and Agriculture Organization of the United Nations. Tuberculosis: www.fao.org/ag/againfo/subjects/en/health/diseases-cards/cards/tuberculosis.html.
9. Rice, D. N.; Rogers, D. G. Johne's Disease (Paratuberculosis): http://ianrpubs.unl.edu/animaldisease/g977.htm, University of Nebraska at Lincoln Institute of Agriculture and Natural Resources.
10. Newton G.L., Bewley C.A., Dwyer T.J., Horn R., Aharonowitz Y., Cohen G., Davies J., Faulkner D.J., and Fahey R.C. Eur. J. Biochem. 230 (1995) 821-825
11. Rawat M., Newton G.L., Ko M., Martinez G.J., Fahey R.C., and Av-Gay Y. Antimicrob. Agents Chemother. 46 (2002) 3348-3355
12. Jardine M.A., Spies H.S., Nkambule C.M., Gammon D.W., and Steenkamp D.J. Bioorg. Med. Chem. 10 (2002) 875-881
13. Lee S., and Rosazza J.P. Org. Lett. 6 (2004) 365-368
14. Qiu D., Shenkin P.S., Hollinger F.P., and Still W.C. J. Phys. Chem. A 101 (1997) 3005-3014
15. Polak E., and Ribiere G. Rev. Fr. Inform. Rech. Operation., Ser. Rouge 16 (1969) 35-37
16. McDonald D.Q., and Still W.C. Tetrahedron Lett. 33 (1992) 7743-7746
17. Cornell W.D., Cieplak P., Bayly C.I., Gould I.R., Merz K.M., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., and Kollman P.A. J. Am. Chem. Soc. 117 (1995) 5179-5197
18. Allinger N.L. J. Am. Chem. Soc. 99 (1977) 8127-8134
19. Allinger N.L., Yuh Y.H., and Lii J.H. J. Am. Chem. Soc. 111 (1989) 8551-8566
20. Halgren T.A. J. Comput. Chem. 20 (1999) 730-748
21. Jorgensen W.L., and Tiradorives J. J. Am. Chem. Soc. 110 (1988) 1657-1666
22. Kaminski G.A., Friesner R.A., Tirado-Rives J., and Jorgensen W.L. J. Phys. Chem. B 105 (2001) 6474-6487
23. Nicholas G.M., Kovác P., and Bewley C.A. J. Am. Chem. Soc. 124 (2002) 3492-3493
24. Chang G., Guida W.C., and Still W.C. J. Am. Chem. Soc. 111 (1989) 4379-4386
25. Ferguson D.M., and Raber D.J. J. Am. Chem. Soc. 111 (1989) 4371-4378
26. Fabricius J., Engelsen S.B., and Rasmussen K. J. Carbohydr. Chem. 16 (1997) 751-772
27. Mahadevan J., Nicholas G.M., and Bewley C.A. J. Org. Chem. 68 (2003) 3380-3386
28. Steffek M., Newton G.L., Av-Gay Y., and Fahey R.C. Biochemistry 42 (2003) 12067-12076
29. Fetterolf B., and Bewley C.A. Bioorg. Med. Chem. Lett. 14 (2004) 3785-3788
30. Nicholas G.M., Eckman L.L., Newton G.L., Fahey R.C., Ray S., and Bewley C.A. Bioorg. Med. Chem. 11 (2003) 601-608
31. Knapp S., Gonzalez S., Myers D.S., Eckman L.L., and Bewley C.A. Org. Lett. 4 (2002) 4337-4339
32. Knapp S., Amorelli B., Darout E., Ventocilla C.C., Goldman L.M., Huhn R.A., and Minnihan E.C. J. Carbohydr. Chem. 24 (2005) 103-130
33. MacroModel 9.0 User Manual (2005), Schrodinger
34. Damm W., Frontera S., Tirado-Rives J., and Jorgensen W.L. J. Am. Chem. Soc. 18 (1997) 1955-1970
35. Vishnyakov A., Widmalm G., Kowalewski J., and Laaksonen A. J. Am. Chem. Soc. 121 (1999) 5403-5412
36. Conrad P.B., and de Pablo J.J. J. Phys. Chem. A 103 (1999) 4049-4055
37. Umemura M., Hayashi S., Nakagawa T., Urakawa H., and Kajiwara K. J. Mol. Struct. (THEOCHEM) 636 (2003) 215-228
38. Starikov E.B., Bräsicke K., Knapp E.W., and Saenger W. Chem. Phys. Lett. 336 (2001) 504-510
39. Leach A.R. Molecular Modelling, Principles and Applications (1996), Addison Wesley Longman Ltd, Harlow, Essex, England
40. van Giessen A.E., and Straub J.E. J. Chem. Phys. 122 (2005) 024904
41. DeMatteo M.P., Snyder N.L., Morton M., Baldisseri D.M., Hadad C.M., and Peczuh M.W. J. Org. Chem. 70 (2005) 24-38
42. Johnson L.N. Acta Crystallogr. 21 (1966) 885-891
43. Boyd J., Porteous R., Soffe N., and Delepierre M. Carbohydr. Res. 139 (1985) 35-46
44. Abraham R.J., Byrne J.J., Griffiths L., and Koniotou R. Magn. Reson. Chem. 43 (2005) 611-624
45. Rabinowitz H.N., and Kraut J. Acta Crystallogr. 17 (1964) 159-168
46. Perez S., Imberty A., Engelsen S.B., Gruza J., Mazeau K., Jimenez-Barbero J., Poveda A., Espinosa J.F., van Eyck B.P., Johnson G., French A.D., Louise M., Kouwijzer C.E., Grootenuis P.D.J., Bernardi A., Raimondi L., Senderowitz H., Durier V., Vergoten G., and Rasmussen K. Carbohydr. Res. 314 (1998) 141-155
47. Brocca P., Bernardi A., Raimondi L., and Sonnino S. Glycoconjugate J. 17 (2000) 283-299
48. Bernardi A., Colombo A., and Sánchez-Medina I. Carbohydr. Res. 339 (2004) 967-973
49. Boström J., Norrby P.-O., and Liljefors T. J. Comput. Aided Mol. Des. 12 (1998) 383-396
50. Nicklaus M.C., Wang S., Driscoll J.S., and Milne G.W.A. Bioorg. Med. Chem. 3 (1995) 411-428
51. Perola E., and Charifson P.S. J. Med. Chem. 47 (2004) 2499-2510
52. Smith L., Azachariah C., Thirumoorthy R., Rocca J., Novák J., Hillman J.D., and Edison A.S. Biochemistry 42 (2003) 10372-10384
53. Greenidge P.A., Mérette S.A.M., Beck R., Dodson G., Goodwin C., Scully M.F., Spencer J., Wiser J., and Deadman J.J. J. Med. Chem. 46 (2003) 1293-1305
54. Thirumoorthy R., Holder J.R., Bauzo R.M., Richards N.G.J., Edison A.S., and Haskell-Luevano C. J. Med. Chem. 44 (2001) 4114-4124
55. Simon C., Barathieu K., Laguerre M., Schmitter J.-M., Fouquet E., Pianet I., and Dufourc E.J. Biochemistry 42 (2003) 10385-10395
56. Neuhaus D., and Williamson M.P. The Nuclear Overhauser Effect in Structural and Conformational Analysis. 2nd ed. (2000), John Wiley and Sons, Toronto