Synthesis of N-Fmoc-α-amino acids carrying the four DNA nucleobases in the side chain

Tetrahedron

Volumn 53, Issue 3, 1997, Pages 1167-1176

  Ciapetti, Paola ^a   Soccolini, Francesco ^b   Taddei, Maurizio ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 BROMOBUTYRIC ACID; ADENINE DERIVATIVE; AMINO ACID DERIVATIVE; CYTOSINE DERIVATIVE; DIPEPTIDE; GUANINE DERIVATIVE; INSECTICIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031032304     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01047-2     Document Type: Article

References (31)

1. Duthaler, R.O. Tetrahedron 1994, 50, 1539.
2. See for example: Walkup, R.D.; Cole, D.C.; Whittlesey, B.R. J.Org. Chem. 1995, 60, 2630.
3. Imperiali, B.; Fisher, S.L. J. Org. Chem. 1992, 57, 757. Gilbertson, S.R.; Wang, X. J. Org. Chem. 1996, 61, 434 and references therein.
4. Imperiali, B.; Fisher, S.L. J. Org. Chem. 1992, 57, 757. Gilbertson, S.R.; Wang, X. J. Org. Chem. 1996, 61, 434 and references therein.
5. Hruby, V.J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249.
6. "Chimera," from ancient greek: "χiμαiρα : goat," was a mythological monster made with a lion head, a goat body and a dragon tail. Homer, Iliad VI, 181-182.
7. Imperiali, B; Roy, R. S. J. Org. Chem. 1995, 60, 1891. Imperiali, B; Roy, R. S. J.Am.Chem.Soc. 1994, 116, 12083.
8. Imperiali, B; Roy, R. S. J. Org. Chem. 1995, 60, 1891. Imperiali, B; Roy, R. S. J.Am.Chem.Soc. 1994, 116, 12083.
9. Lenzi, A., Reginato, G.; Taddei, M. Tetrahedron Lett. 1995, 36, 1713.
10. Lenzi, A.; Reginato, G.; Taddei, M.; Trifilieff, E. Tetrahedron Lett. 1995, 36, 1717.
11. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
12. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
13. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
14. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
15. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
16. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
17. Mulzer, J.; Schr̈der, F.; Lobbia, A.; Buschmann, J.; Luger, P. Angew. Chem. Int. Ed. Engl. 1994, 33, 1737. Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc. Chem. Commun. 1995, 549. Meltzer, P.C.; Liang. A.Y. Matsudaira, P. J. Org. Chem. 1995, 60, 4305. Diederichsen, U.; Schmitt, H.W. Tetrahedron Lett. 1996, 37, 475. Diederichsen, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 445. Umemiya, H;. Kegechika, H.; Hashimoto, Y.; Shudo, K. Nucleos. Nudeot. 1996, 15, 465. Shah, V.J.; Kuntz Jr, I.D.; Kenyon, G.L. Bioorg. Chem. 1996, 24, 194.
18. The protection of the nitrogen group with the fluorenylmethoxycarbonyl group (Fmoc) was chosen as it is considered one of the more suitable for solid phase peptide synthesis. Fields, G.B.; Noble, R.L. Int. J. Pept. Protein. Res. 1990, 35, 161
19. It is authors' opinion that compounds 10,14, 19 and 23 could be of interest to chemists involved in synthesis of new bioactive peptides independently from the preparation of Peptidic Nucleic Acids. In this field the products developed by the Nielsen group in Copenhagen have been largely employed as diagnostics and biochemical probes. For references on this topics see: Haaima, G.; Lohse, A.; Buchardt, O.; Nielsen, P.E. Angew Chem Int. Ed. Engl. 1996, 35, 1339 and references therein. A seris of informative volumes on the argument entitled "Practical PNA" are also available at request from Bioserch, Inc. Beadford, MA.
20. Morino, T.; Nishimoto, M.; Masuda, A.; Fujita, S.; Nishikiori, T.; Saito, S. J. Antibiot. 1995, 48, 1509.
21. For the retrosyntheses in Scheme 1 we were inspired by the following papers: path A: Valerio, R.M.; Alewood, P.F.; Johns, R.B. Synthesis 1988, 786; path B: Baldwin, J.E.; Flinn, A. Tetrahedron Lett. 1987, 31, 3605. Hoffmann, M.G.; Zeis, H.J. Tetrahedron Lett. 1992, 33, 2669; path C: Barton, D.H.R.; Crich, D.; Motherwell, W.B.; Tetrahedron, 1985, 41, 3901.
22. For the retrosyntheses in Scheme 1 we were inspired by the following papers: path A: Valerio, R.M.; Alewood, P.F.; Johns, R.B. Synthesis 1988, 786; path B: Baldwin, J.E.; Flinn, A. Tetrahedron Lett. 1987, 31, 3605. Hoffmann, M.G.; Zeis, H.J. Tetrahedron Lett. 1992, 33, 2669; path C: Barton, D.H.R.; Crich, D.; Motherwell, W.B.; Tetrahedron, 1985, 41, 3901.
23. For the retrosyntheses in Scheme 1 we were inspired by the following papers: path A: Valerio, R.M.; Alewood, P.F.; Johns, R.B. Synthesis 1988, 786; path B: Baldwin, J.E.; Flinn, A. Tetrahedron Lett. 1987, 31, 3605. Hoffmann, M.G.; Zeis, H.J. Tetrahedron Lett. 1992, 33, 2669; path C: Barton, D.H.R.; Crich, D.; Motherwell, W.B.; Tetrahedron, 1985, 41, 3901.
24. For the retrosyntheses in Scheme 1 we were inspired by the following papers: path A: Valerio, R.M.; Alewood, P.F.; Johns, R.B. Synthesis 1988, 786; path B: Baldwin, J.E.; Flinn, A. Tetrahedron Lett. 1987, 31, 3605. Hoffmann, M.G.; Zeis, H.J. Tetrahedron Lett. 1992, 33, 2669; path C: Barton, D.H.R.; Crich, D.; Motherwell, W.B.; Tetrahedron, 1985, 41, 3901.
25. We always purchased 2 from Sigma or Novabiochem.
26. Barton, D.H.R.; Crich, D.; Motherwell, W.B. Tetrahedron Lett. 1983, 24, 4979.
27. Attention, the formation of a dark yellow or a cloudy solution indicates that the ester 4 did not form.
28. Botta, M.; Summa, V.; Saladino, R.; Nicoletti, R. Synth. Commun. 1991, 2181.
29. 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, 6179.
30. Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; Cook, P.I. Anal. Biochem. 1970, 71.
31. Barton, D.H.R; Crich, D; Herve, Y; Potier, P.; Thierry. J; Tetrahedron, 1985, 41, 4347,