Preparation of macrocyclic15N-labelled oligoaminodeoxysaccharides as probes for RNA-binding

Organic and Biomolecular Chemistry

Volumn 2, Issue 23, 2004, Pages 3448-3456

  Jaunzems, Janis ^a   Oelze, Benjamin ^a   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; BINDING ENERGY; CHEMICAL BONDS; ENZYME KINETICS; HYDROGENATION; MACROMOLECULES; NITROGEN; RNA; SYNTHESIS (CHEMICAL);

CHEMICAL SHIFTS; METATHESIS; POLARIZATION TRANSFER; THIN LAYER CHROMATOGRAPHY (TLC);

SACCHARIFICATION;

AMINOGLYCOSIDE; NITROGEN; OLIGOSACCHARIDE; RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METABOLISM; MOLECULAR PROBE; SYNTHESIS;

AMINOGLYCOSIDES; MOLECULAR CONFORMATION; MOLECULAR PROBES; MOLECULAR STRUCTURE; NITROGEN ISOTOPES; OLIGOSACCHARIDES; RNA;

EID: 10644244520     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b412436g     Document Type: Article

References (54)

1. Reviews: (a) W. D. Wilson and K. Li, Curr. Med Chem., 2000, 7, 73-98; (b) G. Werstuck and M. R. Green, Science, 1998, 282, 296-298; (c) D. T. Hung, T. F. Jamison and S. L. Schreiber, Chem. Biol, 1996, 3, 623-639.
2. Reviews: (a) W. D. Wilson and K. Li, Curr. Med Chem., 2000, 7, 73-98; (b) G. Werstuck and M. R. Green, Science, 1998, 282, 296-298; (c) D. T. Hung, T. F. Jamison and S. L. Schreiber, Chem. Biol, 1996, 3, 623-639.
3. Reviews: (a) W. D. Wilson and K. Li, Curr. Med Chem., 2000, 7, 73-98; (b) G. Werstuck and M. R. Green, Science, 1998, 282, 296-298; (c) D. T. Hung, T. F. Jamison and S. L. Schreiber, Chem. Biol, 1996, 3, 623-639.
4. (a) K. Michael and Y. Tor, Chem. Eur. J., 1998, 4, 2091-2098;
5. (b) Y. Tor, ChemBioChem, 2003, 4, 998-1007;
6. Q. Vicens and E. Westhof, ChemBioChem, 2003, 4, 1018-1023; also non aminoglycoside-based oligoamines have served as potent inhibitors of HIV-1 TAR RNA-Tat peptide binding and other RNAs;
7. (d) L. Yu, T. K Oost, J. M. Schkeryantz, J. Yang, D. Janowick and S. W. Fesik, J. Am. Chem. Soc., 2003, 125, 4444-4450;
8. (e) D. Moazed and H. F. Koller, Nature, 1987, 327, 389-394.
9. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
10. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
11. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
12. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
13. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
14. Neomycin was shown to be the most effective triplex groove binder that stabilizes DNA and RNA triple helices with little effect on the double helices. In further studies hybrid structures were designed, based on BBQ and neomycin, with dual recognition ligands that had the potential to be more selective and potent ligands for nucleic acids: (a) D. P. Arya, L. Xuc and P. Tennant, J. Am. Chem. Soc., 2003, 125, 8070-8071; (b) D. P. Arya, R. L. Coffee Jr., B. Willis and A. I. Abramovitch, J. Am. Chem. Soc., 2001.123, 5385-5395; (c) U von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935-941; (d) J. Davies, U. von Ahsen, R. Schroeder, in The RNA World, Cold Spring Harbor Laboratory Press, New York, 1993, p. 185-204; (e) U von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368-370; (f) U von Ahsen and H. F. Noller, Science, 1993, 260, 1500-1503.
15. (a) M. L. Zapp, S. Stern and M. R. Green, Cell (Cambridge, Mass.), 1993, 74, 969-978;
16. (6) M. L. Zapp, D. W. Young, A. Kumar, R. Singh, D. W. Boykin, W. D. Wilson and M. R. Green, Bioorg. Med Chem., 1997, 5, 1149-1155;
17. (c) M. Hendrix, E. S. Priestly, G. F. Joyce and C. Wong, J. Am. Chem. Soc., 1997, 119, 3641-3648.
18. (a) H.-Y. Mei, A. A. Galan, N. S. Halim, D. P. Mack, D. W. Moreland, K. B. Sanders, H. N. Truong and A. W. Czarnik, Bioorg. Med Chem. Lett., 1995, 5, 2755-2760;
19. (b) S. Wang, P. W. Huber, M. Cui, A. W. Czarnik and H.-Y. Mei, Biochemistry, 1998, 37, 5549- 5557;
20. (c) F. Hamy, V. Brondani, A. Flörsheimer, W. Stark, M. J. J. Blommers and T. Klimkait, Biochemistry, 1998, 37, 5086-5095;
21. (d) H.-Y. Mei, M. Cui, A. Heldsinger, S. M. Lemrow, J. A. Loo, K. A. Sannes-Lowry, L. Sharmeen and A. W. Czarnik, Biochemistry, 1998, 37, 14204-14212.
22. (a) D. Fourmy, M. I. Rech, S. C. Blanchard and J. D. Puglisi, Science, 1996, 274, 1269-1432;
23. (b) J. Haddad, P. K. Lakshmi, B. Llano-Sotelo, C. Kim Jr., E. F. Azucenca, M. Liu, S. B. Vakulenko, C. S. Chow and S. Mobashery, J. Am. Chem. Soc., 2002, 124, 3229-3237;
24. H. Wang and Y. Tor, Angew. Chem. Int. Ed., 1998, 37, 117-120; H. Wang and Y. Tor, Angew. Chem. Int. Ed., 1998, 37, 109-111;
25. H. Wang and Y. Tor, Angew. Chem. Int. Ed., 1998, 37, 117-120; H. Wang and Y. Tor, Angew. Chem. Int. Ed., 1998, 37, 109-111;
26. (d) D. J. Earnshaw and M. J. Gait, Nucleic Acids Res., 1998, 26, 5551-5561.
27. (a) T. K. Stage, K. J. Hertel and O. C. Uhlenbeck, RNA, 1995, 1, 95-101;
28. (A) H. Wang and Y Tor, J. Am. Chem. Soc., 1997, 119, 8734-8735;
29. (c) B. Clouet-d'Orval, T. K. Stage and O. C. Uhlenbeck, Biochemistry, 1995, 34, 11186-11190;
30. (d) T. Hermann and E. Westhof, J. Mol. Biol., 1998, 276, 903-912;
31. (e) D. J. Earnshaw and M. J. Gait, Nucleic Acids Res., 1998, 26, 5551-5561;
32. (f) A. Krebs, V. Ludwig, O. Boden and M. W. Goebel, ChemBioChem, 2003, 4, 972-978.
33. E. Kikuta, S. Aoki and E. Kimura, J. Am. Chem. Soc., 2001, 123, 7911-7912.
34. (a) N. W. Luedtke, P. Carmichael and Y. Tor, J. Am. Chem. Soc., 2003, 125, 12374-12375;
35. (b) M. Fridman, V. Belakhov, S. Yaron and T. Baasov, Org. Lett., 2003, 5, 3575-3578.
36. G.-W. Chen and A. Kirschning, Chem. Eur. J., 2002, 8, 2717-2729.
37. M. A. Leeuwenburgh, G. A. Van der Marel and H. S. Overkleeft, Curr. Opin. Chem. Biol., 2003, 7, 757-765.
38. G.-W. Chen, J. Jaunzems, M. Jesberger, M. Kalesse, M. Lindner and A. Kirschning, Tetrahedron, 2004, 60, 15, 3505-3521.
39. J. Jaunzems, D. Kashin, A. Schönberger and A. Kirschning, Eur. J. Org. Chem., 2004, 3435-3446.
40. D. M. Ciment and R. J. Ferner, J. Chem. Soc. C, 1966, 441-445.
41. (a)B. Schmidt, Eur. J. Org. Chem., 2004, 1865-1880;
42. (b) M. K.Gurjar and P. Yakambram, Tetrahedron Lett., 2001, 42, 3633-3636;
43. (c) D. C. Braddock and A. J. Wildsmith, Tetrahedron Lett., 2001, 42, 3239-3242;
44. (d) T. R. Hoye and H. Zhao, Org. Lett., 1999, 1, 1123-1125.
45. W. K. C. Park, M. Auer, H. Jaksche and C.-H. Wong, J. Am. Chem. Soc., 1996, 118, 10150-10155.
46. (a) D. H. R. Barton, P. D. Magnus, J. A. Garbarino and R. N. Young, J. Chem. Soc., Perkin Trans. 1, 1974, 2101-2107;
47. (b) G. A. Olah and J. J. Svobpda, Synthesis, 1972, 307-308.
48. -1).
49. T. A. Halgren, J. Comput. Chem., 1996, 17, 490-519.
50. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440-467.
51. T. Carlomagno, A. Kirschning, unpublished investigations.
52. W. C. Still, A. Tempczyk, R. C. Hawley and T. Hendrickson, J Am. Chem. Soc., 1990, 112, 6127.
53. (a) J. M. Goodman and W. C. Still, J. Comput. Chem., 1991, 12, 1110-1117;
54. (b) H. Senderowitz, F. Guarnieri and W. C. Still, J. Am. Chem. Soc., 1995, 117, 8211-8219.