Dimeric aminoglycosides as antibiotics

Angewandte Chemie - International Edition

Volumn 43, Issue 12, 2004, Pages 1562-1566

  Agnelli, Fabio ^b   Sucheck, Steven J ^a   Marby, Kenneth A ^a   Rabuka, David ^a   Yao, Su Lan ^a   Sears, Pamela S ^a   Liang, Fu Sen ^b   Wong, Chi Huey ^b  

^a Optimer Pharmaceuticals Inc   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Aminoglycosides; Antibiotics; Carbohydrates; Drug design; RNA recognition

Indexed keywords

BACTERIA; RNA; STRAIN;

AMINOGLYCOSIDES; TETHERS;

ANTIBIOTICS;

AMINOGLYCOSIDE ANTIBIOTIC AGENT; TOBRAMYCIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG DESIGN; NONHUMAN; STOICHIOMETRY;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; CARBOHYDRATE SEQUENCE; DIMERIZATION; DRUG DESIGN; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS INFECTIONS; STAPHYLOCOCCUS AUREUS;

EID: 4143076674     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353225     Document Type: Article

References (31)

1. M. K. Kim, D. P. Nicolaou, Infect. Dis. Ther. 2002, 28, 125.
2. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
3. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
4. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
5. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
6. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
7. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
8. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
9. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
10. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
11. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
12. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
13. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
14. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
15. For recent work on aminoglycosides see: B. Llano-Sotelo, E. F. Azucena, L. P. Kotra, S. Mobashery, C. S. Chow, Chem. Biol. 2002, 9, 455; J. Haddad, S. Vakulenko, S. Mobashery, J. Am. Chem. Soc. 1999, 121, 11 922; J. Haddad, L. P. Kotra, B. Llano-Sotelo, C. Kim, E. F. Azucena, M. Liu, S. B. Vakulenko, C. S. Chow, S. Mobashery, J. Am. Chem. Soc. 2002, 124, 3229; S. Hanessian, M. Tremblay, A. Kornienko, N. Moitessier, Tetrahedron 2001, 57, 3255; S. Hanessian, M. Tremblay, E. E. Swayze, Tetrahedron 2003, 59, 983; S. Hanessian, A. Kornienko, E. E. Swayze, Tetrahedron 2003, 59, 995; N. W. Luedtke, Q. Liu, Y. Tor, Biochemistry 2003, 42, 1391; K. Michael, H. Wang, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1951; S. R. Kirk, Y. Tor, Bioorg. Med. Chem. 1999, 7, 1979; S. R. Kirk, N. W. Luedtke, Y. Tor, J. Am. Chem. Soc. 2000, 122, 980; N. W. Luedtke, T. J. Baker, M. Goodman, Y. Tor, J. Am. Chem. Soc. 2000, 122, 12035; Y. Wang, R. R. Rando, Chem. Biol. 1995, 2, 281H. Wang, Y. Tor, Angew. Chem. 1998, 110, 117; Angew. Chem. Int. Ed. 1998, 37, 109.
16. H. Umezawa, I. R. Hooper, Aminoglycoside Antibiotics, Springer, New York, 1982.
17. J. H. Cate, M. M. Yusupov, G. Z. Yusupova, T. N. Earnest, H. F. Noller, Science 1999, 285, 2095.
18. W. M. Clemons, J. L. C. May, B. T. Wimberly, J. P. McCutcheon, M. S. Capel, V. Ramakrishnan, Nature 1999, 400, 833.
19. D. Moazed, H. F. Noller, Nature 1987, 327, 389.
20. P. Nissen, J. Hansen, N. Ban, P. B. Moore, T. A. Steitz, Science 2000, 289, 920.
21. F. Schlunzen, R. Zarivach, J. Harms, A. Bashan, A. Tocilj, R. Albrecht, A. Yonath, F. Franceschi, Nature 2001, 413, 814.
22. B. T. Wimberly, D. E. Brodersen, W. M. Clemons, R. J. Morgan-Warren, A. P. Carter, C. Vonrhein, T. Hartsch, V. Ramakrishnan, Nature 2000, 407, 327.
23. M. M. Yusupov, G. Z. Yusupova, A. Baucom, K. Lieberman, T. N. Earnest, J. H. D. Cate, H. F. Noller, Science 2001, 292, 883.
24. D. Fourmy, M. I. Recht, S. C. Blanchard, J. D. Puglisi, Science 1996, 274, 1367.
25. D. Fourmy, M. I. Recht, J. Puglisi, J. Mol. Biol. 1998, 277, 347.
26. S. R. Lynch, R. L. Gonzalez, J. D. Puglisi, Structure 2003, 11, 43.
27. Q. Vicens, E. Westhof, Chem. Biol. 2092, 9, 747.
28. Q. Vicens, E. Westhof, Structure 2002, 10, 647.
29. Other dimers reported in the literature were based on a monomer with 1:1 stoichiometric binding, thus only slightly improving the affinity. See ref. [2] and S. J. Sucheck, A. L. Wong, K. M. Koeller, D. D. Boehr, K. A. Draker, P. Sears, G. D. Wright, C. H. Wong, J. Am. Chem. Soc. 2000, 122, 5230.
30. d should therefore be in the picomolar range.
31. 2 could also be achieved when fresh catalyst was added after the reaction appeared to stop.