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Title

2-Oxopiperazine-based γ-turn conformationally constrained peptides: Synthesis of CCK-4 analogues

AuthorsHerrero, Susana; García-López, M. Teresa CSIC ; Latorre, Julio; Cenarruzabeitia, Edurne CSIC; Río, Joaquín del CSIC; Herranz, Rosario CSIC ORCID
KeywordsConformation
Molecular structure
Peptides and proteins
Reaction products
Receptors
Issue Date30-Apr-2002
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 67(11): 3866-3873 (2002)
Abstract2-Oxopiperazine derivatives 1 have been designed as mimetics of γ-turn conformationally constrained tripeptides. The synthetic pathway devised for the preparation of both epimers of 1 at C5 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-[Nle31]-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 γ-turn in the bioactive conformation of the C-terminal tripeptide of CCK-4.
Publisher version (URL)http://dx.doi.org/10.1021/jo0256336
URIhttp://hdl.handle.net/10261/335838
DOI10.1021/jo0256336
ISSN0022-3263
E-ISSN1520-6904
Appears in Collections:(IQM) Artículos




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