Fmoc-based solid-phase peptide synthesis using Dpr(Phoc) linker. Synthesis of a C-terminal proline peptide

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9195-9198

  Sola, Régine ^a   Méry, Jean ^a   Pascal, Robert ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PROLINE; TRIPEPTIDE;

ARTICLE; CATALYSIS; CONFORMATION; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; PEPTIDE SYNTHESIS;

EID: 0030590976     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02154-5     Document Type: Article

References (19)

1. 1. Sola, R.; Saguer, P.; David, M.-L.; Pascal, R. J. Chem, Soc., Chem. Commun. 1993, 1786-1788.
2. 2. a) Gisin, B. R; Merrifield, R. B. J. Am. Chem. Soc. 1972, 94, 3102-3106.
3. b) Khosla, M. C.; Smeby, R. R.; Bumpus, F. M. J. Am. Chem. Soc. 1972, 94, 4721-4724.
4. c) Pedroso, E.; Grandas, A.; de las Heras, X.; Eritja, R.; Giralt, E. Tetrahedron Lett. 1986, 27, 743-746.
5. 3. Dalcol, I.; Rabanal, F.; Ludevid, M.-D.; Albericio, F.; Giralt, E. J. Org. Chem. 1995, 60, 7575-7581.
6. 4. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiou, G.; Wenquing, Y.; Schäfer, W. Tetrahedron Lett. 1989, 30, 3943-3946; Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiou, G.; Schäfer, W.; Wenquing, Y. Tetrahedron Lett. 1989, 30, 3947-3950
7. 4. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiou, G.; Wenquing, Y.; Schäfer, W. Tetrahedron Lett. 1989, 30, 3943-3946; Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiou, G.; Schäfer, W.; Wenquing, Y. Tetrahedron Lett. 1989, 30, 3947-3950
8. 5. Akaji, K.; Kiso, Y.; Carpino, L. A. J. Chem. Soc., Chem. Conmun. 1990, 584-586.
9. 6. Kochansky, J.; Wagner, R. M. Tetrahedron Lett. 1992, 33, 8007-8010.
10. 7. Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1996, 37, 4195-4198.
11. 8. The starting resin was prepared from Expansin resin using Boc chemistry as previously described [ref 1]. Expansin resin was a generous gift from Expansia, F-30390 Aramon, France.
12. 9. Milligen 9050 peptide synthesizer. Fmoc protecting group removal by piperidine-DMF (1:4), 7 min.
13. 10. Bz-Pro resin 1b was prepared from Fmoc-Pro resin 1a by deprotection with piperidine-DMF (1:4) (7 min) followed by the reaction of benzoyl chloride in the presence of pyridine in DMF,
14. -3 M solution of PhOH in dry DMF.
15. 12. A 70 % loss of dipeptide was observed during 9 min treatment of Pro-Pro-resin 2c with piperidine-DMF (1:4), followed by DMF washes (6 × 0.5 min).
16. 13. Pascal, R; Sola, R. in preparation.
17. 14. A 20% excess only because of the presence of β-aspartyl and C-terminal carboxyl groups.
18. 15. The extent of the side-reaction with morpholine might be reduced by ca. 50% if the first residue is introduced as a Boc-protected amino acid provided that it has no side-chain protection.
19. 16. A 20 min deprotection time has been recommended for glycopeptide synthesis [Meldal, M.; Bielfeldt, T.; Peters, S.; Jensen, K., J.; Paulsen, H.; Bock, K. Int. J. Pept. Protein Res. 1994, 43, 529-536].