Nucleophilic substitution of protected 2-amino-4-butanoic acid. An easy route to exotic amino acids and conformationally constrained peptides

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3843-3846

  Ciapetti, Paola ^a   Mann, André ^b   Shoenfelder, Angèle ^b   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 BUTANOIC ACID; ALPHA AMINO ACID; BUTYRIC ACID; PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; PROTEIN CONFORMATION; PROTEIN STRUCTURE; SYNTHESIS;

EID: 0032575141     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00628-5     Document Type: Article

References (20)

1. 1. Williams, R. M. Organic Chemistry Series Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. Duthaler, R. O. Tetrahedron 1994, 50, 1539.
2. 1. Williams, R. M. Organic Chemistry Series Volume 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, 1989. Duthaler, R. O. Tetrahedron 1994, 50, 1539.
3. 2. Two representative examples. Petatis, N.A.; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445. Myers, A.G.; Gleason, J.L.; Yoon, T.; King, D.W. J. Am. Chem. Soc. 1997, 119, 656 and references therein.
4. 2. Two representative examples. Petatis, N.A.; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445. Myers, A.G.; Gleason, J.L.; Yoon, T.; King, D.W. J. Am. Chem. Soc. 1997, 119, 656 and references therein.
5. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
6. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
7. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
8. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
9. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
10. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
11. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
12. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
13. 3. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987. Some selected examples:. Ouerfelli, O.; Ishida, M.: Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett, 1993, 409. Williams, L.; Zhang, Z.; Ding, X.; Joullié, M.M. Tetrahedron Lett. 1995, 36, 7031. Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407. D'Aniello, F.; Falorni, M.; Mann, A.; Taddei, M. Tetrahedron Asymmetry 1996, 7, 1217. Walker, M.A.; Kaplita, K.P. ; Chen, T.; King, H.D. Synlett 1997 115. Zhang, L.; Kauffman, G.S.; Pesti, J.A.; Yin, J. J. Org. Chem. 1997, 62, 6918. Tamagnan, G.; Neumeyer, J.L.; Gao, Y.; Wang, S.; Kula, N.S.; Baldessarini, R.J. Bioorg. Med. Chem. Lett. 1997, 7, 337. Gryko, D.; Jurczak, J. Tetrahedron Lett. 1997, 38, 8275.
14. 4 Halogenated amino acids have been used for the generation of nucleophiles with the technique of Jackson : Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210.
15. 5 Lenzi, A. Reginato, G.; Taddei, M. Tetrahedron Lett. 1995, 36, 1713. Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167.
16. 5 Lenzi, A. Reginato, G.; Taddei, M. Tetrahedron Lett. 1995, 36, 1713. Ciapetti, P.; Soccolini, F.; Taddei, M. Tetrahedron 1997, 53, 1167.
17. 6 For the preparation of analogous pyridoxal-amino acid chimerae see: Imperiali, B.; Roy, R.S. J. Org. Chem. 1995, 60, 1891. Imperiali, B.; Roy, R.S. J. Am. Chem. Soc. 1994, 116, 12083.
18. 6 For the preparation of analogous pyridoxal-amino acid chimerae see: Imperiali, B.; Roy, R.S. J. Org. Chem. 1995, 60, 1891. Imperiali, B.; Roy, R.S. J. Am. Chem. Soc. 1994, 116, 12083.
19. 7 Tamm, J.P. in "Peptides, Synthesis, Structures and Applications," B.Gutte Ed, Academic Press, San Diego, 1995, 456.
20. 8 Compounds 17-19 could be introduced, after saponification of the carboxylate, in a polypeptidic structure using a solid phase protocol.