A general synthesis of oligopeptides containing an oxirane ring in the place of a peptidic bond

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2651-2654

  Mann, André ^a   Quaranta, Laura ^b   Reginato, Gianna ^b   Taddei, Maurizio ^c  

^a CENTRE DE NEUROCHIMIE   (France)

^b UNIVERSITY OF FLORENCE   (Italy)

^c UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; OLIGOPEPTIDE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029991378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00352-8     Document Type: Article

References (18)

1. Park, C.; Koh, J. S.; Son, Y. C.; Choi, H.; Lee, C. S.; Choy, N.; Moon, K. Y.; Jung, W. H.; Kim, S. C. Yoon, H. Bioorg. Med. Chem. Lett. 1995, 5, 1843.
2. Albeck, A.; Persky, R.; Kliper, S. Bioorg. Med. Chem. Lett. 1995, 5, 1767. Giordano, C.; Gallina, C.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1990, 25, 479.
3. Albeck, A.; Persky, R.; Kliper, S. Bioorg. Med. Chem. Lett. 1995, 5, 1767. Giordano, C.; Gallina, C.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1990, 25, 479.
4. Kim, D.H.; Kim, K.B.J. J. Am. Chem. Soc. 1991, 13, 3200.
5. Cane, D.E.; Sohng, J-K. Biochemistry, 1994, 33, 6524 and references therein.
6. D'Aniello, F.; Mann, A.; Mattii, D.; Taddei, M. J. Org. Chem. 1994, 59, 3762. Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183.
7. D'Aniello, F.; Mann, A.; Mattii, D.; Taddei, M. J. Org. Chem. 1994, 59, 3762. Ciapetti, P.; Taddei, M.; Ulivi, P. Tetrahedron Lett. 1994, 35, 3183.
8. Gante, J. Angew. Chem. Int. Ed. Eng. 1994, 33, 1699.
9. Jenmalm, A.; Berts, W.; Li, Y-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139. For recent efficent syntheses of trans alkene isosteres see: Daly, M.J.; Ward, R.; Thompson, D.F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. Baresis, R.T.; Masse, C.E.; Panek, J.S. J. Org. Chem. 1995, 60, 7714. Wai, J.S.; Fisher, T.E.; Embrey, M.W. Tetrahedron Lett. 1995, 36, 3461.
10. Jenmalm, A.; Berts, W.; Li, Y-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139. For recent efficent syntheses of trans alkene isosteres see: Daly, M.J.; Ward, R.; Thompson, D.F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. Baresis, R.T.; Masse, C.E.; Panek, J.S. J. Org. Chem. 1995, 60, 7714. Wai, J.S.; Fisher, T.E.; Embrey, M.W. Tetrahedron Lett. 1995, 36, 3461.
11. Jenmalm, A.; Berts, W.; Li, Y-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139. For recent efficent syntheses of trans alkene isosteres see: Daly, M.J.; Ward, R.; Thompson, D.F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. Baresis, R.T.; Masse, C.E.; Panek, J.S. J. Org. Chem. 1995, 60, 7714. Wai, J.S.; Fisher, T.E.; Embrey, M.W. Tetrahedron Lett. 1995, 36, 3461.
12. Jenmalm, A.; Berts, W.; Li, Y-L.; Luthman, K.; Csöregh, I.; Hacksell, U. J. Org. Chem. 1994, 59, 1139. For recent efficent syntheses of trans alkene isosteres see: Daly, M.J.; Ward, R.; Thompson, D.F.; Procter, G. Tetrahedron Lett. 1995, 36, 7545. Baresis, R.T.; Masse, C.E.; Panek, J.S. J. Org. Chem. 1995, 60, 7714. Wai, J.S.; Fisher, T.E.; Embrey, M.W. Tetrahedron Lett. 1995, 36, 3461.
13. This protocol was the only one that (in our hands) guaranteed high yields of N-Cbz-α-amino aldehydes.
14. Annunziata, R.; Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. J. Org. Chem. 1992, 57, 456.
15. Uemura, S.; Ohe, K; Sugita, N. J. Chem. Soc. Chem. Commun. 1988, 111. Ceccherelli, P.; Curini, M.; Epifanio, F.; Marcotullio, M.C. Rosati, O. Tetrahedron Lett. 1995, 36, 5079.
16. Uemura, S.; Ohe, K; Sugita, N. J. Chem. Soc. Chem. Commun. 1988, 111. Ceccherelli, P.; Curini, M.; Epifanio, F.; Marcotullio, M.C. Rosati, O. Tetrahedron Lett. 1995, 36, 5079.
17. Poli, G.; Belvisi, L.; Mantoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165
18. Gennari, C.; Beretta, M.G.; Bernardi, A.; Moro, G.; Scolastico, C.; Todeschini, R. Tetrahedron 1986, 42, 893.