Synthesis of DNA-binding heteroaromatic oligoamides on liquid solid support

Chemical Communications

Volumn , Issue 5, 1998, Pages 605-606

  König, Burkhard ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002116589     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708270c     Document Type: Article

References (23)

1. There are five main peptide structural motifs for DNA-binding that have been identified: helix-tum-helix, zinc finger, leucine zipper, helix-loop-helix and antiparallel β-sheets (β-ribbon). D. S. Johnson and D. L. Boger, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. Davies, D. D. Macnicol, F. Vögtle and J.-M. Lehn, Elsevier Science, Oxford, 1996, vol. 4, p. 77.
2. For a recent example of the regulation of genes expression by small molecules, see: J. M. Gottesfeld, L. Neely, J. W. Trauger, E. E. Baird and P. B. Dervan, Nature, 1997, 387, 202.
3. (a) P. E. Nielsen, Chem. Eur. J. 1997, 3, 505 and references cited therein;
4. (b) The structure of the heteroaromatic peptides was inspired by DNA-binding natural products, such as distamycin or netropsin: D. S. Johnson and D. L. Boger, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. Davies, D. D. Macnicol, F. Vögtle and J.-M. Lehn, Elsevier Science, Oxford, 1996, vol. 4, p. 73;
5. (c) New J. Chem., 1997, 21, 1 (special issue).
6. E. E. Baird and P. B. Dervan, J. Am. Chem. Soc., 1996, 118, 6141.
7. Heteroaromatic oligopeptides with terminal pyridine, thiazole and furan units have been synthesized. These derivatives were expected to bind preferentially G-C rich regions. However, in most cases they still show a preference for A-T regions; K. E. Rao, R. G. Shea, B. Yadagiri and J. W. Lown, Anti-Cancer Drug Des., 1990, 5, 3 (terminal thiazol);
8. M. Lee, R. G. Shea, J. W. Lown and R. T. Pon, J. Mol. Recogn., 1989, 2, 6 (furan);
9. a terminal pyridine has been found to be G-C specific in certain cases: W. S. Wade, M. Mrksich and P. B. Dervan, J. Am. Chem. Soc., 1992, 114, 8783.
10. For the use of poly(ethylene glycol) as support in synthesis, see: M. Mutter, H. Hagenmaier and E. Bayer, Angew. Chem., 1971, 83, 883;
11. Angew. Chem., Int. Ed. Engl., 1971, 10, 811;
12. R. N. V. Pillai and M. Mutter, Top. Curr. Chem., 1982, 106, 119;
13. D. J. Graven and K. D. Janda, Chem. Rev., 1997, 97, 489;
14. combinatorial libraries: H. Han, M. M. Wolfe, S. Brenner and K. D. Janda, Proc. Natl. Acad. Sci. USA, 1995, 92, 6419.
15. The coupling with DCC-DMAP gave 6 in a lower yield of 92%.
16. M. A. Tilak and C. S. Hollinden, Tetrahedron Lett., 1968, 1297.
17. M. Mrksich, M. E. Parks and P. B. Dervan, J. Am. Chem. Soc., 1994, 116, 7983. MeO-PEG support is not suitable for a direct synthesis of extended structures due to the known alteration of its physical properties with growing oligoamide chain length. This leads to incomplete precipitation.
18. B. König, H. Buchholz, M. Rödel and M. Schulze, patent pending.
19. Recent example: S. M. Touami, C. C. Poon and P. A. Wender, J. Am. Chem. Soc., 1997, 119, 7611.
20. Many carbo- or hetero-cyclic aromatic nitro carboxylic acids are readily available; 4-nitrothiophene-2-carboxylic acid: M. Römer, Chem. Ber., 1887, 20, 116;
21. ethyl-1-methyl-4-nitroimidazole- 2-carboxylate: K. Krowicki and J. W. Lown, J. Org. Chem., 1987, 52, 3493;
22. 5-nitrothiophene-2-carboxylic acid: P. Cogolli, F. Maiolo, L. Testaferri, M. Tiecco and M. Tingoli, J. Chem. Soc., Perkin Trans. 2, 1980, 1331;
23. 2-nitrothiazole-5-carboxylic acid: W. Knauf, Eur. J. Med. Chem. Chim. Ther., 1975, 10, 533.