Hydrazinolysis of Dde: Complete orthogonality with Aloc protecting groups

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1175-1178

  Rohwedder, Barbara ^a   Mutti, Yvan ^a   Dumy, Pascal ^a   Mutter, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; FUNCTIONAL GROUP; PEPTIDE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0032485517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10810-3     Document Type: Article

References (18)

1. 1. Abbrevations used in this article: Aloc, allyloxycarbonyl; Fmoc, 9-fluorenylmethoxycarbonyl; Boc, t-butoxycarbonyl; Dde, 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl.
2. 2. Alsina, J.; Rabanal, F.; Giralt, E.; Albericio, F. Tetrahedron Letters, 1994, 35, 9633-9636.
3. 3. Zhang, W.; Taylor, J. W. Tetrahedron Letters, 1996, 37, 2173-2176.
4. 4. Eichler, J.; Lucka, A. W.; Houghten, R. A. in Peptides 1994; Chemistry and Biology 23th Proc. Eur. Pept. Symp. 1995, Eds.; Maia, H., ESCOM, Leiden, 461-462.
5. 4. Eichler, J.; Lucka, A. W.; Houghten, R. A. in Peptides 1994; Chemistry and Biology 23th Proc. Eur. Pept. Symp. 1995, Eds.; Maia, H., ESCOM, Leiden, 461-462.
6. 5. Dumy, P.; Eggleston I., Servigni, S.; Sila, U; Sun, X.; Mutter, M. Tetrahedron Letters, 1995, 36, 1255-1258; Ernest, I.; Kalvoda, J.; Sigel, C.; Rihs, G.; Fritz, H.; Blommers, M.; Raschdorf, F.; Francotte, E.; Mutter, M. Helv. Chim. Acta, 1993, 76, 1539; Sila, U.; Mutter, M. J. Mol. Recognition, 1995, 8, 29-34; M. Mutter; P. Dumy; P. Garrouste; C. Lehmann; M. Mathieu; C. Peggion; S. Peluso; A. Razaname; G. Tuchscherer Angew. Chem. Int. Ed. Engl. 1996, 35, 1482-1485.
7. 5. Dumy, P.; Eggleston I., Servigni, S.; Sila, U; Sun, X.; Mutter, M. Tetrahedron Letters, 1995, 36, 1255-1258; Ernest, I.; Kalvoda, J.; Sigel, C.; Rihs, G.; Fritz, H.; Blommers, M.; Raschdorf, F.; Francotte, E.; Mutter, M. Helv. Chim. Acta, 1993, 76, 1539; Sila, U.; Mutter, M. J. Mol. Recognition, 1995, 8, 29-34; M. Mutter; P. Dumy; P. Garrouste; C. Lehmann; M. Mathieu; C. Peggion; S. Peluso; A. Razaname; G. Tuchscherer Angew. Chem. Int. Ed. Engl. 1996, 35, 1482-1485.
8. 5. Dumy, P.; Eggleston I., Servigni, S.; Sila, U; Sun, X.; Mutter, M. Tetrahedron Letters, 1995, 36, 1255-1258; Ernest, I.; Kalvoda, J.; Sigel, C.; Rihs, G.; Fritz, H.; Blommers, M.; Raschdorf, F.; Francotte, E.; Mutter, M. Helv. Chim. Acta, 1993, 76, 1539; Sila, U.; Mutter, M. J. Mol. Recognition, 1995, 8, 29-34; M. Mutter; P. Dumy; P. Garrouste; C. Lehmann; M. Mathieu; C. Peggion; S. Peluso; A. Razaname; G. Tuchscherer Angew. Chem. Int. Ed. Engl. 1996, 35, 1482-1485.
9. 5. Dumy, P.; Eggleston I., Servigni, S.; Sila, U; Sun, X.; Mutter, M. Tetrahedron Letters, 1995, 36, 1255-1258; Ernest, I.; Kalvoda, J.; Sigel, C.; Rihs, G.; Fritz, H.; Blommers, M.; Raschdorf, F.; Francotte, E.; Mutter, M. Helv. Chim. Acta, 1993, 76, 1539; Sila, U.; Mutter, M. J. Mol. Recognition, 1995, 8, 29-34; M. Mutter; P. Dumy; P. Garrouste; C. Lehmann; M. Mathieu; C. Peggion; S. Peluso; A. Razaname; G. Tuchscherer Angew. Chem. Int. Ed. Engl. 1996, 35, 1482-1485.
10. 6. Guibé, F.; Dangles, O.; Balavoine, G.; Loffet, A. Tetrahedron Letters, 1989, 30, 2641-2244; Kunz, H. Angew. Chem. Int. Ed. Engl. 1987, 26, 294-308.
11. 6. Guibé, F.; Dangles, O.; Balavoine, G.; Loffet, A. Tetrahedron Letters, 1989, 30, 2641-2244; Kunz, H. Angew. Chem. Int. Ed. Engl. 1987, 26, 294-308.
12. 7. Bloomberg, G.B.; Askin, D.; Gargaro, A.R.; Tanner, M.J.A. Tetrahedron Letters, 1993, 34, 4709.
13. 8. ESI-MS analysis have been performed on a HPLC-ESI-MS coupled apparatus.
14. 3CN/TFA 9/90/1) 40% B to 100% B in 30 min) t=37.2 min.
15. 3J = 4.3Hz; 1.71, 2H m; 4.02ppm, 2H t, 6.6 Hz) are consistent with attribution of 3.
16. 11. Cusack, N.; J.; Reese, C. B.; Risius, A. C.; Roozpeikar, B. Tetrahedron, 1976, 32, 2157-2162.
17. 12. The side reaction have been observed with larger molecules as well as with peptides containing several Dde and / or Aloc protected lysine side-chain. For each of them a different reaction rates is observed.
18. 13. The product was stable during 24h as inferred by HPLC.