Synthesis and evaluation of glucosamine-6-phosphate analogues as activators of glmS riboswitch

Tetrahedron

Volumn 68, Issue 46, 2012, Pages 9405-9412

  Wang, Guan Nan ^a   Lau, Pui Sai ^b   Li, Yingfu ^b   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

Antibiotics; Carbohydrate; GlcN6P analogues; glmS Riboswitch; Synthesis

Indexed keywords

(4 AMINO 2,3,5 TRIHYDROXYCYCLOHEXYL)METHYL DIHYDROGEN PHOSPHATE; (5 AMINO 3,4,6 TRIHYDROXYTETRAHYDRO 2H PYRAN 2 YL)(HYDROXY)METHYLPHOSPHONIC ACID; ANTIBIOTIC AGENT; GLUCOSAMINE 6 PHOSPHATE ANALOG; GLUCOSAMINE DERIVATIVE; GLUTAMINE FRUCTOSE 6 PHOSPHATE AMINOTRANSFERASE; METHYLPHOSPHONIC ACID; RIBOZYME; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVATION; ENZYME INDUCTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN CLEAVAGE; RIBOSWITCH; STRUCTURE ACTIVITY RELATION;

BACILLUS SUBTILIS; POSIBACTERIA;

EID: 84867063026     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.015     Document Type: Article

References (38)

1. W. Winkler, A. Nahvi, and R.R. Breaker Nature 419 2002 952 956
2. R.L. Coppins, K.B. Hall, and E.A. Groisman Curr. Opin. Microbiol. 10 2007 176 181
3. K.F. Blount, and R.R. Breaker Nat. Biotechnol. 24 2006 1558 1564
4. J.E. Barrick, K.A. Corbino, W.C. Winkler, A. Nahvi, M. Mandal, J. Collins, M. Lee, A. Roth, N. Sudarsan, I. Jona, J.K. Wickiser, and R.R. Breaker Proc. Natl. Acad. Sci. U.S.A. 101 2004 6421 6426
5. D.J. Klein, and A.R. Ferre-D'Amare Science 313 2006 1752 1756
6. J.C. Cochrane, S.V. Lipchock, and S.A. Strobel Chem. Biol. 14 2007 97 105
7. W.C. Winkler, A. Nahvi, A. Roth, J.A. Collins, and R.R. Breaker Nature 428 2004 281 286
8. S. Milewski Biochim. Biophys. Acta 1597 2002 173 192
9. H.C. Wu, and T.C. Wu J. Bacteriol. 105 1971 455 466
10. M. Sarvas J. Bacteriol. 105 1971 467 471
11. E.B. Freese, R.M. Cole, W. Klofat, and E. Freese J. Bacteriol. 101 1970 1046 1062
12. P.Y. Watson, and M.J. Fedor Nat. Struct. Mol. Biol. 18 2011 359 363
13. B. Gong, D.J. Klein, A.R. Ferre-D'Amare, and P.R. Carey J. Am. Chem. Soc. 133 2011 14188 14191
14. J.H. Davis, B.F. Dunican, and S.A. Strobel Biochemistry 50 2011 7236 7242
15. K.M. Brooks, and K.J. Hampel Biochemistry 50 2011 2424 2433
16. T.J. McCarthy, M.A. Plog, S.A. Floy, J.A. Jansen, J.K. Soukup, and G.A. Soukup Chem. Biol. 12 2005 1221 1226
17. J. Lim, B.C. Grove, A. Roth, and R.R. Breaker Angew. Chem., Int. Ed. 45 2006 6689 6693
18. R. Engel Chem. Rev. 77 1977 349 367
19. A. Kraszewski, and J. Stawinski Pure Appl. Chem. 79 2007 2217 2227
20. C. Thibaudeau, P. Acharya, and J. Chattopadhyaya Stereoelectronic Effects in Nucleosides and Nucleotides and Their Structural Implications 2005 Uppsala University Uppsala
21. D.H.R. Barton, S. Augydorey, J. Camara, P. Dalko, J.M. Delaumeny, S.D. Gero, B. Quicletsire, and P. Stutz Tetrahedron 46 1990 215 230
22. K.S. Ko, C.J. Zea, and N.L. Pohl J. Am. Chem. Soc. 126 2004 13188 13189
23. R. Eby, S.J. Sondheimer, and C. Schuerch Carbohydr. Res. 73 1979 273 276
24. G.N. Wang, G. Twigg, T.D. Butters, S. Zhang, L. Zhang, L.-H. Zhang, and X.-S. Ye Org. Biomol. Chem. 10 2012 2923 2927
25. A.N. Pudovik, and I.V. Konovalova Synthesis 1979 81 96
26. R.A. Cherkasov, V.I. Galkin, A.B. Khabibullina, and K. Alkurdi Phosphorus, Sulfur Silicon Relat. Elem. 49 1990 61 64
27. J.A. Dale, and H.S. Mosher J. Am. Chem. Soc. 95 1973 512 519
28. J.A. Dale, D.L. Dull, and H.S. Mosher J. Org. Chem. 34 1969 2543 2549
29. T.R. Hoye, C.S. Jeffrey, and F. Shao Nat. Protoc. 2 2007 2451 2458
30. S.S. Ng, and T.F. Jamison Tetrahedron 61 2005 11405 11417
31. O.I. Kolodiazhnyi Tetrahedron: Asymmetry 16 2005 3295 3340
32. R.F. Frechette, C. Ackerman, S. Beers, R. Look, and J. Moore Bioorg. Med. Chem. Lett. 7 1997 2169 2172
33. J.F. Dellaria Jr., R.G. Maki, H.H. Stein, J. Cohen, D. Whittern, K. Marsh, D.J. Hoffman, J.J. Plattner, and T.J. Perun J. Med. Chem. 33 1990 534 542
34. T.P. Kee, and T.D. Nixon J.-P. Majoral, New Aspects in Phosphorus Chemistry II; Topics in Current Chemistry vol. 223 2003 Springer Berlin 45 65
35. J.P. Abell, and H. Yamamoto J. Am. Chem. Soc. 130 2008 10521 10523
36. C.E. Lunse, M.S. Schmidt, V. Wittmann, and G. Mayer ACS Chem. Biol. 6 2011 675 678
37. D.J. Klein, M.D. Been, and A.R. Ferre-D'Amare J. Am. Chem. Soc. 129 2007 14858 14859
38. Y. Xin, and D. Hamelberg RNA 16 2010 2455 2463