Synthesis of stable aminoacyl-tRNA analogues containing triazole as a bioisoster of esters

Chemistry - A European Journal

Volumn 15, Issue 8, 2009, Pages 1929-1938

  Chemama, Maryline ^a   Fonvielle, Matthieu ^b,c,d   Arthur, Michel ^b,c,d   Valéry, Jean Marc ^a   Etheve Quelquejeu, Melanie ^a  

^a Centre National de la Recherche Scientifique   (France)

^b CENTRE DE RECHERCHE DES CORDELIERS   (France)

^c SORBONNE UNIVERSITÉ   (France)

^d UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Aminoacyl tRNA click chemistry; Dinucleotides; Inhibitors; Triazoles

Indexed keywords

ACETYLENE; AMINO ACIDS; BACTERIOLOGY; CELL MEMBRANES; ESTERIFICATION; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACIDS; RNA;

AMINOACYL-TRNA CLICK CHEMISTRY; BACTERIAL CELLS; BACTERIAL PATHOGENS; BIOLOGICAL PROCESS; CYCLOADDITIONS; DEOXYADENOSINE; DINUCLEOTIDES; INHIBITORS; NMR SPECTROSCOPIES; PEPTIDOGLYCAN; PHOSPHORAMIDITE; PROTEASOME; PROTEIN SYNTHESIS; REGIO-ISOMERS; TRIAZOLE RINGS; TRIAZOLES;

ESTERS;

AMINOACYL TRANSFER RNA; AMINOACYLTRANSFERASE; ESTER; TRIAZOLE DERIVATIVE;

ARTICLE; BIOLOGICAL MODEL; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; IC 50; NUCLEOTIDE SEQUENCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINOACYLTRANSFERASES; BASE SEQUENCE; ESTERS; INHIBITORY CONCENTRATION 50; MODELS, BIOLOGICAL; MODELS, CHEMICAL; MOLECULAR STRUCTURE; RNA, TRANSFER, AMINO ACYL; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 60649122048     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801563     Document Type: Article

References (53)

1. J. Van Heijenoort, Nat. Prod. Rep. 2001, 18, 503-519.
2. K. H. Schleifer, O. Kandler, Bacteriol. Rev. 1972, 36, 407-477.
3. a) J. L. Mainardi, R. Villet, T. D. Bugg, C. Mayer, M. Arthur. FEMS Microbiol. Rev. 2008, 32, 386-408;
4. b) S. Biarrotte-Sorin, A. Maillard, J. Delettré, W. Sougakoff, M. Arthur, C. Mayer, Structure 2004, 12, 257-267;
5. c) T. E. Benson, D. B. Prince, V. T. Mulchler, K. A. Curry, A. M. Ho, R. W. Sarver, J. C. Hagadorn, G. H. Choi, R. L. Garlick, Structure 2002, 10, 1107-1115;
6. d) S. S. Hedge, T. E. Shrader, J. Biol. Chem. 2001, 276, 6998-7003.
7. C. Goffin, J.-M. Ghuysen. Microbiol. Mol. Biol. Rev. 2002, 66, 702-738.
8. U. Kopp, M. Roos, J. Wecke, H. Labischinski, Microb. Drug Resist. 1996, 2, 29-41.
9. M. Chemama, M. Fonvielle, R. Villet, M. Arthur, J.-M. Valéry, M. Elheve-Quelquejeu, J. Am. Chem. Soc. 2007, 129, 12642-12643.
10. a) J. Rudolph, H. Theis, R. Hanke, L. Endermann, F-U. Geschke, J. Med. Chem. 2001, 44, 619-626;
11. b) W. R. Tully, C. R. Gardner, R. J. Gillespie, R. Westwood, J. Med. Chem. 1991, 34, 2060-2067;
12. c) F. Watjen, R. Baker, M. Engelsloff, R. Herbert, A. MacLeod, A. Knight, K. Merchant, J. Moseley, J. Saunders, C. J. Swain, E. Wong, J. P. Springer, J. Med. Chem. 1989, 32, 2282-2291.
13. a) L. Moreira, E. J. Barreiro, Curr. Med. Chem. 2005, 12, 23-49;
14. b) S. B. Orlek, F. E. Blaney, F. Brown, M. S. G. Clark, M. S. Hadley, J. Hatcher, G. J. Riley, H. E. Rosenberg, H. J. Wadworth, P. Wyman, J. Med. Chem. 1991, 34, 2726-2273.
15. a) K. S. Huang, J. S. Weinger, E. B. Butler, S. A. Strobel, J. Am. Chem. Soc. 2006, 128, 3108-3109;
16. b) T. Schmeing, K. S. Huang, S. A. Strobel, T. Steitz, Nature 2005, 438, 520-524;
17. c) J. S. Weinger, D. Kitchen, S. A. Scaringe, S. A. Strobel, G. W. Muth, Nucleic Acids Res. 2004, 32, 1502-1511;
18. d) A. Charafeddine, W. Dayoub, H. Chapuis, P. Strazewski, Chem. Eur. J. 2007, 13, 5566-5584.
19. E. Cressina, A. J. Lloyd, G. De Pascale, D. I. Roper, C. G. Dowson, T. D. Bugg, Bioorg. Med. Chem. Lett. 2007, 17, 4654-4656.
20. For reviews see: a) V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68;
21. b) H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137;
22. c) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075;
23. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
24. R. Huisgen in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), Wiley, New York, 1984, pp. 1-176.
25. a) V. V. Rostovlsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711;
26. Angew. Chem. Int. Ed. 2002, 41, 2596-2599;
27. b) C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
28. a) A. Jatsch, A. Kopyshev, E. Mena-Osteritz, P. Baeuerle, Organic Letters, 2008, 10, 961-964;
29. b) F. Seela, V.R. Sirivolu, Helv. Chim. Acta 2007, 90, 535-548;
30. c) I. Kosiova, S. Kovackova, P. Kois, Tetrahedron 2007, 63, 312-320;
31. d) J. Gierlich, G. A. Burley, P. M. E. Gramlich, D. M. Hammond, T. Carell, Org. Lett. 2006, 8, 3639-3642;
32. e) L. V. Lee, M. L. Mitchell, S.-J. Huang, V. V. Fokin, K. B. Sharpless, C.-H. Wong, J. Am. Chem. Soc. 2003, 125, 9588-9589;
33. f) T. S. Seo, Z. Li, H. Ruparel, J. Ju, J. Org. Chem. 2003, 68, 609-612.
34. a) L. Li, B. Lin, Z. Yang, L. Zhang, L. Zhang, Tetrahedron Lett. 2008, 49, 4491-4493;
35. b) Y. Xia, W. Li, F. Ou, Z. Fan, X. Liu, C. Berro, E. Rauzy, L. Peng, Org. Biomol. Chem. 2007, 5, 1695-1701;
36. c) L. Cosyn, K. K. Palaniappan, S.-K. Kim, H. T. Duong, Z.-G. Gao, K. A. Jacobson, S. V. Calenbergh, J. Med. Chem. 2006, 49, 7373-7383.
37. a) J. Broggi, S. Diez-Gonzalez, J. L. Petersen, S. Berteina-Raboin, S. P. Nolan, L. A. Agrofoglio, Synthesis 2008, 141-148;
38. b) H. Skarpos, S. N. Osipov, D. V. Vorob'eva, I. L. Odinets, E. Lork, G.-V. Roschenthaler, Org. Biomol. Chem. 2007, 5, 2361-2367;
39. c) M. Tourirte, T. Oulih, H. B. Lazrek, J. L. Barascut, J. L. Imbach, N. A. Almasoudi, Nucleosides Nucleotides Nucleic Acids 2003, 22, 1985-1993.
40. a) R. Lucas, V. Neto, A. Hadj Bouazza, R. Zerrouki, R. Granet, P. Krausz, Y. Champavier, Tetrahedron Lett. 2008, 49, 1004-1007;
41. b) R. Kumar, A. El-Sagheer, J. Tumpane, P. Lincoln, L. M. Wilhelmsson, T. Brown, J. Am. Chem. Soc. 2007, 129, 6859-6864.
42. a) T. G. Heckler, Y. Zama, T. Naka, S. M. Hecht, Biol. Chem. 1983, 258, 4492-4495;
43. b) T. G. Heckler, L. H. Chang, Y. Zama, T. Naka, S. M. Hecht, Tetrahedron 1984, 40, 87-94;
44. c) T. G. Heckler, L. H. Chang, Y. Zama, T. Naka, M. S. Chorghade, S. M. Hecht, Biochemistry 1984, 23, 1468-1473.
45. a) M. M. Majireck, S. M. Weinreb, J. Org. Chem. 2006, 71, 8680-8683;
46. b) L. Zhang, X. Chen, P. Xue, H. H. Y. Sun, I. D. Williams, K. B. Sharpless, V. V. Fokin, G. Jia, J. Am. Chem. Soc. 2005, 127, 15998-15999.
47. K. Beom-Tae, K. Seung-Ki, L. Seung-Jae, H. Ki-Jun, Bull. Korean Chem. Soc. 2004, 25, 243-248.
48. a) S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521-522;
49. b) B. M. Trost, G. J. Roth, Org. Lett. 1999, 1, 67-70;
50. c) H. D. Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett. 2004, 45, 5597-5599.
51. S. A. Robertson, C. J. Noren, S. J. Anthony-Cahill, M. C. Griffith, P. G. Schultz, Nucleic Acids Res. 1989, 17, 9649-9660.
52. A. Maillard, S. Biarrotte-Sorin, R. Villet, S. Mesnage, A. Bouhss, W. Sougakoff, C. Mayer, M. Arthur, J. Bacteriol. 2005, 187, 3833-3838.
53. R. Villet, M. Fonvielle, P. Busca, M. Chemama, A. Maillard, J.-E. Hugonnet, L. Dubost, A. Marie, N. Josseaume, S. Mesnage, V. Delfosse, C. Mayer, J.-M. Valéry, M. Ethève-Quelquejeu, M. Arthur, Nucleic Acids Res. 2007, 35, 6870-6883.