Design and synthesis of aminoglycoside antibiotics to selectively target 16S ribosomal RNA position 1408

Helvetica Chimica Acta

Volumn 88, Issue 11, 2005, Pages 2967-2985

  Pathak, Rashmi ^a   Böttger, Erik C ^b   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLATION; RNA; SYNTHESIS (CHEMICAL);

BENZYLIDENE ACETALS; FLUORODEHYDROXYLATION; RIBOSOMES;

ANTIBIOTICS;

1,3,2''',6''' TETRAAMMONIUM (2 DEAMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL)PAROMOMYCIN TETRAACETATE; 1,3,2',2''',6''' PENTAAMMONIUM 6' DEOXY 6' FLUOROPAROMOMYCIN PENTAKIS(TRIFLUOROACETATE); 1,3,2',2''',6''' PENTAAMMONIUM 6' DEOXYPAROMOMYCIN PENTAKIS(TRIFLUOROACETATE); 1,3,2',2''',6''' PENTADEAMINO 3',6' ANHYDRO 1,3,2',2''',6''' PENTAAZIDOPAROMOMYCIN; 3',6' ANHYDROPAROMOMYCIN 1,3,2',2''',6''' PENTAAMMONIUM PENTAACETATE; 6,2'',5'',3''',4''' PENTA O ACETYLDE(2 AMINO 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSYL) 1,3,2''',6''' TETRAKIS[N [(TERT BUTOXY)CARBONYL]]PAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 1,3,2',2''',6''' PENTADEAMINO 1,3,2',2''',6''' PENTAAZIDO 4' O BENZOYL 6' BROMO 6' DEOXYPAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 1,3,2',2''',6''' PENTADEAMINO 1,3,2',2''',6''' PENTAAZIDO 4',6' O BENZYLIDENEPAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 1,3,2',2''',6''' PENTAKIS[N [(TERT BUTOXY)CARBONYL]] 6' DEOXY 6' FLUOROPAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 1,3,2',2''',6''' PENTAKIS[N [(TERT BUTOXY)CARBONYL]]PAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 4' O BENZOYL 6' BROMO 1,3,2',2''',6''' PENTAKIS[N [(TERT BUTOXY)CARBONYL]] 6' DEOXYPAROMOMYCIN; 6,3',2'',5'',3''',4''' HEXA O ACETYL 4',6' O BENZYLIDENE 1,3,2',2''',6''' PENTAKIS[N [(TERT BUTOXY)CARBONYL]]PAROMOMYCIN; AMINOGLYCOSIDE ANTIBIOTIC AGENT; FRAMYCETIN; GENTAMICIN; KANAMYCIN A; KANAMYCIN B; PAROMOMYCIN; RIBOSOME RNA; TOBRAMYCIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; DEACETYLATION; DEPROTECTION REACTION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENOLYSIS; HYDROXYLATION; PRIORITY JOURNAL; REDUCTION; RIBOSOME;

EID: 28444494783     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590240     Document Type: Article

References (36)

1. T. Auerbach, Curr. Drug Targets Infect. Disord. 2002, 2, 169.
2. C. M. T. Spahn, C. D. Prescott, J. Mol. Med. 1996, 74, 423.
3. E. Cundliffe, in 'The Ribosome: Structure, Function and Evolution', American Society for Microbiology, Washinghton, DC, 1990, p. 479-490;
4. E. Cundliffe, in 'The Molecular Basis of Antibiotic Action', Eds. E. F. Gale, E. Cundliffe, P. E. Reynolds, M. H. Richmond, and M. J. Waring, John Wiley & Sons, New York, 1981, p. 402-547.
5. S. Campuzano, D. Vazquez, J. Modolell, Biochem. Biophys. Res. Commun. 1979, 87, 960.
6. E. C. Böttger, B. Springer, T. Prammananan, Y. Kidan, P. Sander, EMBO Rep. 2001, 2, 318.
7. T. Auerbach, A. Bashan, A. Yonath, Trends Biotechnol. 2004, 22, 570.
8. Q. Vicens, E. Westhof, J. Mol. Biol. 2003, 326, 1175;
9. Q. Vicens, E. Westhof, Chem. Biol. 2002, 9, 747.
10. Q. Vicens, E. Westhof, Structure 2001, 9, 647.
11. A. P. Carter, W. M. Clemons, D. E. Brodersen, R. J. Morgan-Warren, B. T. Wimberly, V. Ramakrishnan, Nature 2000, 407, 340.
12. Q. Han, Q. Zhao, S. Fish, K. B. Simonsen, D. Vourloumis, J. M. Froelich, D. Wall, T. Hermann, Angew. Chem., Int. Ed. 2005, 44, 2694.
13. H. F. Chambers, M. A. Sande, in 'Goodman & Gilman's The Phamacoligal Basis of Therapeutics', Eds. J. G. Hardman and L. E. Limbird, McGraw-Hill, London, 1996, p. 1103.
14. D. Fourmy, M. I. Recht, J. D. Puglisi, J. Mol. Biol. 1998, 277, 347;
15. D. Fourmy, M. I. Recht, S. C. Blanchard, J. D. Puglisi, Science 1996, 274, 1367.
16. P. Sander, T. Prammananan, E. C. Böttger, Mol. Microbiol. 1996, 22, 841.
17. T. Prammananan, P. Sander, B. A. Brown, K. Frischkorn, G. O. Onyi, Y. S. Zhang, E. C. Böttger, R. J. Wallace, J. Infect. Dis. 1998, 177, 1573.
18. M. I. Recht, S. Douthwaite, J. D. Puglisi, EMBO J. 1999, 18, 3133.
19. S. Hanessian, T. Takamoto, R. Masse, G. Patil, Can. J. Chem. 1978, 56, 1482.
20. S. Hanessian, N. R. Plessas, J. Org. Chem. 1969, 34, 1035;
21. S. Hanessian, N. R. Plessas, J. Org. Chem. 1969. 34, 1045;
22. S. Hanessian, N. R. Plessas, J. Org. Chem. 1969, 34, 1053.
23. A. N. Eberle, A. Zeller, Helv. Chim. Acta 1985, 68, 1880.
24. B. Bernet, A. Vasella, Helv. Chim. Acta 1979, 62, 1990;
25. B. Bernet, A. Vasella, Helv. Chim. Acta 1979, 62, 2400;
26. B. Bernet, A. Vasella, Helv. Chim. Acta 1979, 62, 2411;
27. B. Bernet, A. Vasella, Helv. Chim. Acta 1984, 67, 1328.
28. A. Vasella, C. Witzig, J. L. Chiara, M. Martín-Lomas, Helv. Chim. Acta 1991, 74, 2073.
29. P. B. Alper, S. C. Hung, C. H. Wong, Tetrahedron Lett. 1996, 37, 6029.
30. P. T. Nyffeler, C. H. Liang, K. M. Koeller, C. H. Wong, J. Am. Chem. Soc. 2002, 124, 10773.
31. A. Fürstner, J. Baumgartner, D. N. Jumbam, J. Chem. Soc., Perkin Trans. 1 1993, 131.
32. G. O. Aspinall, D. Chatterjee, L. Khondo, Can. J. Chem. 1984, 62, 2728.
33. T. Prammananan, P. Sander, B. Springer, E. C. Böttger, Antimicrob. Agents Chemother. 1999, 43, 447.
34. P. Pfister, S. Hobbie, Q. Vicens, E. C. Böttger, E. Westhof, ChemBioChem 2003, 4, 1078;
35. P. Pfister, S. Hobbie, C. Brüll, N. Corti, A. Vasella, E. Westhof, E. C. Böttger, J. Mol. Biol. 2005, 346, 467.
36. E. Bozó, A. Vasella, Helv. Chim. Acta 1992, 75, 2613.