Hybridization properties of aromatic peptide nucleic acids: A novel class of oligonucleotide analogues

Organic Letters

Volumn 4, Issue 1, 2002, Pages 63-66

  Fader, Lee D ^a   Tsantrizos, Youla S ^a,b  

^a MCGILL UNIVERSITY   (Canada)

^b BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; OLIGONUCLEOTIDE; PEPTIDE NUCLEIC ACID; RNA;

ARTICLE; CHEMISTRY; NUCLEIC ACID HYBRIDIZATION;

DNA; NUCLEIC ACID HYBRIDIZATION; OLIGONUCLEOTIDES; PEPTIDE NUCLEIC ACIDS; RNA;

EID: 0037050469     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010231q     Document Type: Article

References (30)

1. (a) Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624-630.
2. (b) Nielsen, P. E. Curr. Opin. Struct. Biol. 1999, 9, 353-357.
3. Hanvey, J. C.; Peffer, N. J.; Bisi, J. E.; Thomson, S. A.; Cadila, R.; Josey, J. A.; Ricca, D. J.; Hassman, C. F.; Bonham, M. A.; Au, K. G.; Carter, S. G.; Bruckenstein, D. A.; Boyd, A. L.; Noble, S. A.; Babiss, L. E. Science 1992, 258, 1481.
4. (a) Bergmeier, S. C.; Fundy, S. L. Bioorg. Med. Chem. Lett. 1997, 7, 3135.
5. (b) Zhang, L.; Min, J.; Zhang, L. Bioorg. Med. Chem. Lett. 1999, 9, 2903.
6. (c) Kuwahara, M.; Arimitsu, M.; Sisido, M. J. Am. Chem. Soc. 1999, 121, 256.
7. (d) Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624.
8. (e) Schütz, R.; Cantin, M.; Roberts, C.; Greiner, B.; Uhlmann, E.; Leumann, C. Angew. Chem., Int. Ed. 2000, 39, 1250.
9. (f) Efimov, V. A. Buryakova, A. A.; Choob, M. V.; Chakhmakcheva, O. G. Nucleosides Nucleotides 1999, 18, 1393.
10. (g) Puschl, A.; Boesen, T.; Zuccarello, G.; Dahl, O.; Pitsch, S.; Nielsen, P. E. J. Org. Chem. 2001, 66, 707.
11. (h) Pueschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
12. (i) D'Costa, M.; Kumar, V.; Ganesh, K. N. Org. Lett. 2001, 3, 1269.
13. (j) Vilaivan, T.; Suparpprom, C.; Harayuttanakorn, P.; Lowe, G. Tetrahedron Lett. 2001, 42, 5533-5536.
14. Tsantrizos, Y. S.; Lunetta, J. F.; Boyd, M.; Fader, L. D.; Wilson, M.-C. J. Org. Chem. 1997, 62, 5451.
15. Fader, L. D.; Boyd, M.; Tsantrizos, Y. S. J. Org. Chem. 2001, 66, 3372.
16. 2H, see: Coull, J. M.; Hodge, R. P. Patent WO, 95/17403, 1995.
17. 2H, see: Thomson, S. A.; Josey, J. A.; Cadilla, R.; Gaul, M. D.; Hassman, C. F.; Luzzio, M. J.; Pipe, A. J.; Reed, K. L.; Ricca, D. J.; Wiethe, R. W.; Noble, S. A. Tetrahedron 1995, 51(22), 6179-6194.
18. 2H was synthesized using an independent method.
19. (a) Chang, C.-D.; Felix, A. M.; Jimenez, M. H.; Meienhofer, J. Int. J. Pept. Protein Res. 1980, 15, 485.
20. (b) Peptide and Peptidomimetic Synthesis. Reagents for Drug Discovery; Fluka Chemie GmbH: Buchs, 2000; p 123.
21. (a) Christensen, L.; Fitzpatrick, R.; Gildea, B.; Petersen, K. H.; Hansen, H. F.; Koch, T.; Egholm, M.; Buchardt, O.; Nielsen, P. E.; Coull, J.; Berg, R. H. J. Pept. Sci. 1995, 3, 175.
22. (b) Christensen, L.; Fitzpatrick, R.; Gildea, B.; Petersen, K. H.; Hansen, H. F.; Koch, T.; Egholm, M.; Buchardt, O.; Nielson, P. E. J. Pept. Sci. 1995, 1(3), 185.
23. Job, P. Ann. Chim. (Paris) 1928, 9, 113-203.
24. (a) Hyrup, B.; Egholm, M.; Nielson, P. E.; Wittung, P.; Nordén, B.; Buchardt, O. J. Am. Chem. Soc. 1994, 116, 7964.
25. (b) Sforza, S.; Haaima, G.; Marchelli, R.; Nielsen, P. E. Eur. J. Org. Chem. 1999, 197, 7-204.
26. In some cases the N-terminal of the oligomers are capped with an acetate unit in order to prevent acyl transfer of the last nucleobase-carboxymethyl moiety. However, this measure was not taken with chimeras 14-17 since the sequences studied in ref 13 were not capped in this way. For comments on the influence a positively charged N-terminal has on the stability of PNA:DNA complexes, see: Egholm, M.; Buchardt, O.; Nielsen, P. E.; Berg, R. H. J. Am. Chem. Soc. 1992, 114, 1895.
27. m value given for this PNA sequence in refs 10a,b was 50°C in the case of the antiparallel complex.
28. Smith, J. O.; Olson, D. A.; Armitage, B. A. J. Am. Chem. Soc. 1999, 121, 2686-2695.
29. 2(5). The authors of ref 13 have demonstrated that the dye binds with very low affinity to parallel PNA complexes.
30. n:ssAPNA-PNA aggregate was not responsible for the observed spectral changes.