| 2-Oxopiperazine-based gamma-turn conformationally constrained peptides: synthesis of CCK-4 analogues. | |
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MedLine Citation:
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PMID: 12027705 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Susana Herrero; M Teresa García-López; Miriam Latorre; Edurne Cenarruzabeitia; Joaquín Del Río; Rosario Herranz |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 67 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2002 May |
Date Detail:
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Created Date: 2002-05-24 Completed Date: 2002-11-19 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 3866-73 Citation Subset: IM |
Affiliation:
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Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Cerebral Cortex / metabolism Models, Molecular Molecular Mimicry Nuclear Magnetic Resonance, Biomolecular Pancreas / metabolism Peptides / chemical synthesis*, chemistry, metabolism Piperazines / chemical synthesis, chemistry*, metabolism Protein Conformation Rats Receptor, Cholecystokinin B Receptors, Cholecystokinin / metabolism Tetragastrin / analogs & derivatives*, metabolism |
| Chemical | |
Reg. No./Substance:
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0/Peptides; 0/Piperazines; 0/Receptor, Cholecystokinin B; 0/Receptors, Cholecystokinin; 1947-37-1/Tetragastrin |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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