431059-48-2Relevant academic research and scientific papers
2-Oxopiperazine-based gamma-turn conformationally constrained peptides: synthesis of CCK-4 analogues.
Herrero, Susana,Garcia-Lopez, M Teresa,Latorre, Miriam,Cenarruzabeitia, Edurne,Del Rio, Joaquin,Herranz, Rosario
, p. 3866 - 3873 (2007/10/03)
2-Oxopiperazine derivatives 1 have been designed as mimetics of gamma-turn conformationally constrained tripeptides. The synthetic pathway devised for the preparation of both epimers of 1 at C(5) involves a reductive amination of cyanomethyleneamino pseudopeptides with amino acid derivatives, followed by regiospecific lactamization of the resulting C-backbone branched pseudopeptides. The versatility of this methodology is illustrated in the synthesis of analogues of the tetrapeptides Boc-[Nle(31)]-CCK-4 and Boc-[Lys(o-tolylaminocarbonyl)(31)]-CCK-4. The introduction of the new conformational restriction into these Boc-CCK-4 analogues led to a loss of 2 or 3 orders of magnitude in the affinity at CCK receptors. These results suggest the absence of a gamma-turn in the bioactive conformation of the C-terminal tripeptide of CCK-4.
C-Backbone branched peptides via reductive amination of cyanomethyleneamino pseudopeptides
Herrero, Susana,Suárez-Gea, M.Luisa,García-López, M.Teresa,Herranz, Rosario
, p. 1421 - 1424 (2007/10/03)
The synthesis of branched peptides from cyanomethylenamino pseudopeptides, via catalytic hydrogenation in the presence of amino acid derivatives, is described. When the inserted amino acid was a glycine derivative, the resulting branched peptide lactamize
