Synthesis of hydrazinopeptides using solid phase N-amination. Application to chemical ligation

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7259-7262

  Klinguer, Christine ^a   Melnyk, Oleg ^a   Loing, Estelle ^a   Gras Masse, Hélène ^a  

^a INSTITUT PASTEUR DE LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PH; REACTION ANALYSIS; TECHNIQUE;

EID: 0030607189     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01661-9     Document Type: Article

References (15)

1. 1 Loing, E.; Delanoye, A.; Sergheraert, C., Tartar, A.; Gras-Masse, H. Pep. Research, submitted.
2. 2 Déprez, B.; Sauzet, J.-P.; Boutillon, C.; Martinon, F.; Tartar, A.; Sergheraert, C.; Guillet, J.-G.; Gomard, E.; Gras-Masse, H. Vaccine 1996, 14, 375-382.
3. 3 King, T.E.; Zhao, S.W.; Lam, T. Biochemistry 1986, 25, 5774-5779. Gaertner, H.F.; Rose, K.; Cotton, R.; Timms, D.; Camble, R.; Offord, R.E. Bioconjugate Chem. 1992, 3, 262-268.
4. 3 King, T.E.; Zhao, S.W.; Lam, T. Biochemistry 1986, 25, 5774-5779. Gaertner, H.F.; Rose, K.; Cotton, R.; Timms, D.; Camble, R.; Offord, R.E. Bioconjugate Chem. 1992, 3, 262-268.
5. 4 a) Vidal, J.; Drouin, J.; Collet, A. J. Chem. Soc. Chem. Commun. 1991, 435-437.
6. b) Vidal, J.; Guy, L.; Stérin, S.; Collet, A. J. Org. Chem. 1993, 58, 4791-4793.
7. c) Aubry, A.; Mangeot, J.-P.; Vidal, J.; Collet, A.; Zerkout, S.; Marraud, M. Int. J. Peptide Protein Res. 1994, 43, 305-311.
8. 2. For the last cycle, 100 μL of DIEA were added after 15 min to neutralize acidic impurities.
9. γ 1.36.
10. 7 a) Schmidt, U.; Riedl, B. Synthesis 1993, 809-814.
11. b) Hosmane, R.S.; Bhadti, V.S.; Lim, B.B. Synthesis 1990, 1095-1100.
12. 3CN : 1 / 2 containing 18 μL of cyclohexanecarboxaldehyde. The pH of the medium was adjusted with aqueous NaOH 1N and the solution stirred at rt.
13. + = 1768 by TOF-PDMS, co-eluting by HPLC with the starting peptide 1).
14. + = 1880 by TOF-PDMS.
15. γ 1.40; CH-C(OH)NH 2.11; methylene protons of the cyclohexyl moiety 1.71-1.63-1.35-1.29-1.20.