Corrigendum to "Probing the ribosomal RNA A-site with functionally diverse analogues of paromomycin-synthesis of ring I mimetics". [Tetrahedron 63 (2007) 827-846] (DOI:10.1016/j.tet.2006.10.079);Probing the ribosomal RNA A-site with functionally diverse analogues of paromomycin-synthesis of ring I mimetics

Tetrahedron

Volumn 63, Issue 4, 2007, Pages 827-846

  Hanessian, Stephen ^a   Adhikari, Susanta ^a   Szychowski, Janek ^a   Pachamuthu, Kandasmy ^a   Wang, Xiaojing ^b   Migawa, Michael T ^c   Griffey, Richard H ^c   Swayze, Eric E ^c  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^c ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYSTREPTAMINE; 5'' O (3 PHENYLPROPYL 1 AMINOETHYL)PAROMOMYCIN; 5'' O HYDROXYETHYL NORPAROMOMYCIN; ALIPHATIC COMPOUND; AROMATIC COMPOUND; HYDROXYL GROUP; PAROMOMYCIN; RIBOSOME RNA;

ALKYLATION; ARTICLE; CELL ASSAY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; INHIBITION KINETICS; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS;

STAPHYLOCOCCUS AUREUS;

EID: 33845439127     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.161     Document Type: Erratum

References (82)

1. In: Mitsuhashi S. (Ed). Aminoglycoside Antibiotics Drug Action and Drug Resistance in Bacteria Vol. 2 (1975), University Park Press, Tokyo
2. Mingeot-Leclercq M.P., and Tulkens P.M. Antimicrob. Agents Chemother. 43 (1999) 1003
3. Mingeot-Leclercq M.P., Glupczynski Y., and Tulkens P.M. Antimicrob. Agents Chemother. 43 (1999) 727
4. Magnet S., and Blanchard J.S. Chem. Rev. 105 (2005) 477
5. Fong D.H., and Berghuis A.M. EMBO J. 21 (2002) 2323
6. Smith C.A., and Baker E.N. Curr. Drug Targets Infect. Disord. 2 (2002) 143
7. Davies J. Science 264 (1994) 375
8. Shaw K.J., Rather P.N., Hare R.S., and Miller G.H. Microbiol. Rev. 57 (1993) 138
9. Haddad J., Kotra L.P., Llano-Sotelo B., Kim C., Azucena Jr. E.F., Liu M., Vakulenko S.B., Chow C.S., and Mobashery S. J. Am. Chem. Soc. 124 (2002) 3229
10. See for example:
11. Rai R., Chen H.-N., Czyryca P.G., Li J., and Chang C.-W.T. Org. Lett. 8 (2006) 887
12. Rosenbohm C., Vanden Berghe D., Vlietinck A., and Wengel J. Tetrahedron 57 (2001) 6277
13. Ding Y., Swayze E.E., Hofstadler S.A., and Griffey R.H. Tetrahedron Lett. 41 (2000) 4049
14. Sucheck S.J., Greenberg W.A., Tolbert J.J., and Wong C.-H. Angew. Chem., Int. Ed. 39 (2000) 1080
15. Michael K., Wang H., and Tor Y. Bioorg. Med. Chem. Lett. 7 (1999) 1361
16. Nunns C.L., Spence L.A., Slater M.J., and Berrisford D.J. Tetrahedron Lett. 40 (1999) 9341
17. Roestamadji J., and Mobashery S. Bioorg. Med. Chem. Lett. 8 (1998) 3483 and references cited therein
18. For reviews on RNA-binding small molecules, see:
19. Tok J., Bi H., and Bi L. Curr. Top. Med. Chem. 3 (2003) 1001
20. Tor Y. ChemBioChem 4 (2003) 998
21. Ye X.-S., and Zhang L.H. Curr. Med. Chem. 9 (2002) 929
22. Hermann T. Angew. Chem., Int. Ed. 39 (2000) 1890
23. Tor Y. Angew. Chem., Int. Ed. 38 (1999) 1579
24. Hermann T., and Westhof E. Curr. Opin. Biotechnol. 9 (1998) 66
25. Pearson N.D., and Prescott C.D. Chem. Biol. 4 (1997) 409
26. In: Gesteland R.F., Cech T.R., and Atkins J.F. (Eds). The RNA World. 2nd ed. (1999), Cold Springs Harbor Laboratory, New York, NY
27. In: Nagai K., and Mattaj I.W. (Eds). RNA-Protein Interactions (1994), IRL, New York, NY and references cited therein
28. Parsek M.R., and Singh P.K. Annu. Rev. Microbiol. 57 (2003) 677
29. Noller H.F. Science 309 (2005) 1508
30. Woodcock J., Moazed D., Cannon M., Davies J., and Noller H.F. EMBO J. 10 (1991) 3099
31. Gale E.F., Cundliffe E., Reynolds P.E., Richmond M.H., and Waring M.J. The Molecular Basis of Antibiotic Action (1981), Wiley, London
32. Moazed D., and Noller H.F. Nature 327 (1987) 389
33. For excellent reviews, see:. Green R., and Noller H.F. Chem. Biol. 4 (1997) 679
34. Noller H.F. Annu. Rev. Biochem. 60 (1991) 191
35. Cundliffe E. Recognition Sites for Antibiotics within rRNA. In: Hill W.E., et al. (Ed). The Ribosome: Structure, Function, and Evolution (1990), American Society for Microbiology, Washington, DC 479
36. Wimberley B.T., Brodersen D.E., Clemons J.W.M., Morgan-Warren R.J., Caster A.P., Vonrhein C., Hartsek T., and Ramakrishnan V. Nature 407 (2000) 327
37. See for example:
38. Recht M.I., Fourmy D., Blanchard K.D., Dahlquist D., and Puglisi J.D. J. Mol. Biol. 286 (1999) 33
39. Fourmy D., Recht M.I., Blanchard S.C., and Puglisi J.D. Science 274 (1996) 1367
40. Hofstadler S.A., and Griffey R.H. Curr. Opin. Drug Discovery Dev. 3 (2000) 423
41. Griffey R.H., Hofstadler S.A., Sannes-Lowery K.A., Ecker D.J., and Crooke S.T. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 10129
42. Griffey R.H., Greig M.J., An H., Sasmor H., and Manalili S. J. Am. Chem. Soc. 121 (1999) 474
43. Fourmy D., Yoshizawa S., and Puglisi J.D. J. Mol. Biol. 277 (1998) 333
44. Fourmy D., Recht M.I., and Puglisi J.D. J. Mol. Biol. 277 (1998) 347
45. Lynch S.R., Gonzalez Jr. R.L., and Puglisi J.D. Structure 11 (2003) 43
46. Carter A.P., Clemons W.M., Bordersen D.E., Morgan-Warren R.J., Wimberly B.T., and Ramakrishnan V. Nature 407 (2000) 340
47. Vicens Q., and Westhof E. Structure 9 (2001) 647
48. Vicent Q., and Westhof E. J. Mol. Biol. 326 (2003) 1175
49. Pfister P., Hobbie S., Vicens Q., Böttger E.C., and Westhof E. ChemBiochem 4 (2003) 1078
50. Ogle J.M., Brodersen D.E., Clemons Jr. W.M., Tarry M.J., Carter A.P., and Ramakrishnan V. Science 292 (2001) 897
51. Moitessier N., Hanessian S., and Westhof E. J. Med. Chem. 49 (2006) 1023
52. Hermann T., and Westhof E. J. Med. Chem. 42 (1999) 1250
53. Leclerc F., and Cedergren R. J. Med. Chem. 41 (1998) 175
54. See for example:
55. Hanessian S., Takamoto T., Massé R., and Patil G. Can. J. Chem. 56 (1978) 1482
56. Hanessian S., Massé R., and Eckborg G. Can. J. Chem. 56 (1978) 1492
57. Hanessian S., Tremblay M., and Swayze E.E. Tetrahedron 59 (2003) 983
58. Hanessian S., Kornienko A., and Swayze E.E. Tetrahedron 59 (2003) 995
59. Hanessian S., Tremblay M., Kornienko A., and Moitessier N. Tetrahedron 57 (2001) 3255
60. Garegg P.J., and Samuelsson B. J. Chem. Soc., Perkin Trans. 1 (1980) 2866
61. Hanessian S., Masse R., and Nakagawa T. Can. J. Chem. 56 (1978) 1509
62. Cheung T.M., Horton D., and Weckerle W.G. Carbohydr. Res. 58 (1977) 139
63. Ferrier R.J. J. Chem. Soc., Perkin Trans. 1 (1979) 1455
64. Blattner R., Ferrier R.J., and Prasit P. J. Chem. Soc., Chem. Commun. (1980) 944
65. Bernet B., and Vasella A. Helv. Chim. Acta 62 (1979) 1990
66. Liotta L.J., Lee J., and Ganem B. Tetrahedron 47 (1981) 2433
67. Kleban M., Kautz W., Greul J., Hilgers P., Kugler R., Dong H.-Q., and Jäger V. Synthesis 7 (2000) 1027
68. Pathak R., Böttger E.C., and Vasella A. Helv. Chim. Acta 88 (2005) 2967
69. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
70. Boeckman Jr. R.K., Shao P., and Mullins J.J. Org. Synth. 77 (2000) 141
71. Ding Y., Hofstadler S.A., Swayze E.E., and Griffey R.H. Org. Lett. 3 (2001) 1621
72. Ding Y., Hofstadler S.A., Swayze E.E., Risen L., and Griffey R.H. Angew. Chem., Int. Ed. 42 (2003) 3409
73. Wang X., Migawa M.T., Sannes-Lowery K.A., and Swayze E.E. Bioorg. Med. Chem. Lett. 15 (2005) 4919
74. Pearlman W.M. Tetrahedron Lett. (1967) 1663
75. Wu B., Yang J., He Y., and Swayze E.E. Org. Lett. 4 (2002) 3455
76. Hanessian S., Ogawa T., and Takamoto T. Can. J. Chem. 56 (1978) 1500
77. Griffey R.H., Sannes-Lowery K.A., Drader J.J., Mohan V., Swayze E.E., et al. J. Am. Chem. Soc. 122 (2000) 9933
78. Luedtke N.W., Liu Q., and Tor Y. Biochemistry 42 (2003) 11391
79. Lee J., Kwon M., Lee K.H., Jeong S., Hyun S., Shin K.J., and Yu J. J. Am. Chem. Soc. 126 (2004) 1956
80. Alper P.B., Hendrix M., Sears P., and Wong C.-H. J. Am. Chem. Soc. 120 (1998) 1965
81. François B., Szychowski J., Adhikari S.S., Pachamuthu K., Swayze E.E., Griffey R.H., Migawa M.T., Westhof E., and Hanessian S. Angew. Chem., Int. Ed. 43 (2004) 6735
82. For 5″-carboxamide and related analogues of paromomycin, see: Kudyba, I.; Fernandez, D. P.; Böttger, E. C.; Vasella, A. Carbohydr. Res., in press.