Solid-phase synthesis of N,N'-unsymmetrically substituted ureas: Application to the synthesis of carbaza peptides

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2749-2752

  Limal, David ^a,b   Semetey, Vincent ^a   Dalbon, Pascal ^b   Jolivet, Michel ^b   Briand, Jean Paul ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b BIOMÉRIEUX   (France)

Author keywords

Isocyanates; Peptide analogues mimetics; Solid phase synthesis; Ureas

Indexed keywords

ALPHA AMINO ACID; AMINE; CARBAMIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PHOSGENE; POLYMER; PSEUDOPEPTIDE; UREA DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; IMMUNOLOGICAL PROCEDURES; MOLECULAR MIMICRY; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN ASSEMBLY; REACTION ANALYSIS; RNA TRANSLATION;

EID: 0033515726     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00288-9     Document Type: Article

References (15)

1. Mendre, C.; Rodriguez, M.; Lignon M.F.; Galas, M.C.; Worms, P.; Martinez, J. European J. Pharmacol. 1990, 186, 213-222.
2. Gante, J. Synthesis. 1989, 405-413 and references therein.
3. Spatola, A.F. Peptide backbone modifications: A structure-activity analysis of peptides containing amide bond surrogates, conformational constraints, and related backbone replacements. In Chemistry and Biochemistry of Amino Acids, Peptide and Proteins; Weinstein, B. Ed.; Marcel Dekker, Inc.: New York and Basel, 1983, Vol. 7, 267-357.
4. Burgess, K.; Ibarzo, J.; Linthicum, S.; Russel, D.H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A.J. J. Am. Chem. Soc. 1997, 119, 1556-1564.
5. Hutchins, S.M.; Chapman, K.T. Tetrahedron Lett. 1995, 36, 2583-2586.
6. Quibell, M.; Turnell, W.G.; Johnson, T. J. Chem. Soc. Perkin Trans. I 1993, 2843-2849.
7. Zhang, X.; Rodrigues, J.; Evans, L.; Hinkle, B.; Ballantyne, L.; Peña, M. J. Org. Chem. 1997, 62, 6420-6423.
8. Majer, P.; Randad, R.S. J. Org. Chem. 1994, 59, 1937-1938.
9. Limal, D.; Quesnel, A.; Briand, J.P. Tetrahedron Lett. 1998, 39, 4239-4242.
10. Nahm, S.; Weinreb, S.M. Tetrahedron Lett. 1981, 22, 3815-3818.
11. Fehrentz, J.A.; Castro, B. Synthesis. 1982, 676-678.
12. Abdel-Magid, AF.; Carson, K.G.; Harris, B.D.; Maryanoff, C.A.; Shah, B.D. J. Org. Chem. 1996, 61, 3849-3862.
13. Lemaire-Audoire, S.; Savignac, M.; Genêt, J-.P. Tetrahedron Lett. 1995, 36, 6109-6113.
14. +).
15. Limal, D.; Briand, J.P.; Dalbon, P.; Jolivet, M. J. Peptide Res. 1998, 52, 121-129.