Synthesis of peptides using palladium promoted selective removal of allyloxycarbonyl protecting groups in aqueous medium

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 2955-2958

  Lemaire Audoire, Sandrine ^a   Savignac, Monique ^a   Blart, Errol ^a   Bernard, Jean Marie ^b   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PROTEIN PURIFICATION; REACTION ANALYSIS;

EID: 0030938480     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00535-2     Document Type: Article

References (14)

1. Abbreviations used in this paper. DCC : 1,3-dicyclohexylcarbodiimide; dimethylallyl : 3-methylbut-2-enyl; HOBT : 1-hydroxybenzotriazole; PPA : tripropylphosphoric anhydride; TBTU : 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate; TPPTS : triphenylphosphinotrisulfonate sodium salt.
2. Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149-2154..
3. a) Carpino, L.A.; Cohen, B.E.; Stephens, K.Y.; Sadat-Aalaee, S.Y.; Tien, J-T.; Langridge, D.C. J. Org. Chem. 1986, 51, 3732-3734.
4. b) Hoeg-Jensen, T.; Hasteen Jakobsen, M.; Holm, A. Tetrahedron Lett. 1991, 32, 6387-6390.
5. SAPPHO : in french : Synthèse Automatisée de Peptides en Phase HOmogène Bernard, J.M.; Bouzid, K.; Casati, J.P.; Galvez, M.; Gervais, C.; Meilland, P.; Pevere, V.; Vandewalle, M.F.; Badey, J.P.; Enderlin, J.M. The Roots of Organic Developments Desmurs, J.R.; Ratton, S. Eds., Elsevier, 1996, p 405.
6. a) Lemaire-Audoire, S.; Blart, E.; Savignac, M.; Pourcelot, G.; Genêt, J.P. Tetrahedron Lett. 1994, 35, 8783-8786;
7. b) Lemaire-Audoire, S.; Blart, E.; Savignac, M.; Pourcelot, G.; Genêt, J.P. J. Mol. Catal. 1997, 116, 247.
8. a) König, W.; Geiger, R. Ber. Dtsch. Ges. 1970, 103, 2024;
9. b) Bodansky, M. Peptide Chemistry, A Practical Textbook, Springer-Verlag: Berlin, 1988, p 67.
10. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927-1930.
11. Wissmann, H.; Kleiner, H.J. Ang. Chem. Int. Ed. Engl. 1980, 19, 123-124.
12. a) The Peptides Gross, E.; Meienhofer, J., Eds., Academic Press. New-York, 1979; Vol 1;
13. b) Bodansky, M. Principles of Peptide Synthesis, Springer-Verlag: Berlin, 1984.
14. 20 = - 4 (c = 0.81, DMF). F = 193°C.