β-Homoalanyl PNAs: Synthesis and Indication of Higher Ordered Structures

Angewandte Chemie - International Edition

Volumn 37, Issue 3, 1998, Pages 302-305

  Diederichsen, Ulf ^a   Schmitt, Harald W ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Amino acids; Mitsunobu reaction; Nucleic acids; Peplide nucleic acids; Supramolecular chemistsry

Indexed keywords

EID: 0032536554     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980216)37:3<302::AID-ANIE302>3.0.CO;2-4     Document Type: Article

References (33)

1. a) M. Egholm, O. Buchardt, L. Christensen, C. Behrens, S. M. Freier, D. A. Driver, R. H. Berg, S. K. Kim, B. Nordén, P. E. Nielsen, Nature 1993, 365, 566;
2. b) B. Hyrup, P. E. Nielsen, Bioorg. Med. Chem. 1996, 4, 3.
3. P. Wittung, P. E. Nielsen, O. Buchardt, M. Egholm, B. Nordén, Nature 1994, 368, 561.
4. a) U. Diederichsen, Angew. Chem. 1996, 108, 458; Angew. Chem. Int. Ed. Engl. 1996, 35, 445:
5. a) U. Diederichsen, Angew. Chem. 1996, 108, 458; Angew. Chem. Int. Ed. Engl. 1996, 35, 445:
6. b) U. Diederichsen, H. W. Schmitt, Tetrahedron Lett. 1996, 37, 475.
7. U. Diederichsen, D. Weicherding, unpublished results.
8. U. Diederichsen, Bioorg. Med. Chem. Lett. 1997, 7, 1743.
9. a) E. Juaristi, D. Quintana, J. Escalante, Aldnchim. Acta 1994, 27, 3;
10. b) D. C. Cole, Tetrahedron 1994, 50, 9517;
11. J. Podlech, D. Seebach, Angew. Chem. 1995, 107, 507; Angew. Chem. Int. Ed. Engl. 1995, 34, 471;
12. J. Podlech, D. Seebach, Angew. Chem. 1995, 107, 507; Angew. Chem. Int. Ed. Engl. 1995, 34, 471;
13. Liebigs Ann. Chem. 1995, 1217;
14. e) N. N. Romanova, A. G. Gravis, Y. G. Bundel, Russ. Chem. Rev. 1996, 65, 1083.
15. a) T. F. Jenny, N. Previsani, S. A. Benner, Tetrahedron Lett. 1991, 32, 7029;
16. b) M. L. Peterson, R. Vince, J. Med. Chem. 1991, 34, 2787;
17. A. Toyota, N. Katagiri, C. Kaneko, Synth. Commun. 1993, 23, 1295:
18. M. R. Harnden, A. Parkin, M. J. Parratt, R. M. Perkins, J. Med. Chem. 1993, 36, 1343;
19. e) A. Bouali, D. F. Ewing, G. Mackenzie, Nudeosides Nucleotides 1994, 13, 491.
20. Homoserine derivative 2 was obtained in 95% yield by reduction of the C-terminal carbonyl group of Boc-Asp(Bzl)OH in analogy to G. Kokotos, Synthesis 1990, 299.
21. a) Z. Kazimierczuk, H. B. Cottam, G. R. Revankar, R. K. Robins, J. Am. Chem. Soc. 1994, 106, 6379;
22. b) F. R. Benson, T. W. Hartzel, E. A. Otten, ibid. 1954, 76, 1858.
23. H. Kessler, S. Seip in Two-Dimensional NMR Spectroscopy (Eds.: W. R. Croasmun, R. M. K. Carlson), 2nd ed., VCH, Weinheim, 1994, p. 619.
24. a) W. Saenger, Principles of Nucleic Acid Structure, Springer, New York, 1983;
25. b) I. Berger, C. Kang, A. Fredian, R. Ratliff, R. Moyzis, A. Rich. Nat. Struct. Biol. 1995, 2, 416;
26. K. J. Baejens, H. L. De Bondt, A. Pardi, S. R. Holbrook, Proc. Natl Acad. Sci. USA 1996, 93, 12851.
27. J. Hunziker, H.-J. Roth, M. Böhringer, A. Giger, U. Diederichsen, M. Göbel, R. Krishnan, B. Jaun, C. Leumann, A. Eschenmoser, Helv. Chim. Acta 1993, 76, 259.
28. U. Diederichsen, Angew. Chem. 1997, 109, 1966: Angew. Chem. Int. Ed. Engl. 1997, 36, 1886.
29. U. Diederichsen, Angew. Chem. 1997, 109, 1966: Angew. Chem. Int. Ed. Engl. 1997, 36, 1886.
30. 1 helix. For β-peptides, compare with a) D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913;
31. b) D. Seebach, P. E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, ibid. 1996, 79, 2043;
32. D. H. Appella, L. A. Christianson, I. L. Karle, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 13071;
33. D. H. Appella, L. A. Christianson, D. A. Klein, D. R. Powell, X. Huang, J. J. Barch, Jr., S. H. Gellman, Nature 1997, 387, 381. The conformation of β-PNA should not be helical because of the base-pair distances of 5 Å and the maximum of two bases on top of each other, which leads to a substantial loss of stacking interactions.