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Closed Access item Ketomethylene and (Cyanomethy1ene)amino Pseudopeptide Analogues of the C-Terminal Hexapeptide of Neurotensin

Authors:González-Muñiz, Rosario
García-López, M. Teresa
Gomez-Monterrey, Isabel
Herranz, Rosario
Jimeno, M. Luisa
Suarez-Gea, M . Luisa
Johansen, Nils L.
Madsen, Kjeld
Thøgersen, Henning
Issue Date:1995
Publisher:American Chemical Society
Citation:Journal of Medicinal Chemistry 38 : 1015-1021 (1995)
Abstract:A series of pseudopeptide analogues of the C-terminal hexapeptide of neurotensin (NT8-13), namely [Tyr11Y[COCH21Phe121-,[ Ile12Y[COCH21Phe131-a, nd [Tyr11Y[CH(CN)NHlIle121NT8-13 with different stereochemistries, has been synthesized and evaluated for its potency in displacing labeled NT from rat cortex membranes. Ketomethylene pseudohexapeptides were prepared from the corresponding Boc-protected ketomethylene dipeptide derivatives, previously formed, using different solid phase synthesis (SPS) conditions, while (cyanomethy1ene)amino analogues were directly prepared by SPS using Fmoc strategy. H-Arg-Arg-Pro-TyrY[COCH21- Phe-Leu-OH was nearly as potent as NT8-13 and [Phel2lNT8-l3 in binding to the receptor. Comparison of the affinities for the pseudohexapeptides, here reported, with those of the Y- [CHzNH] analogues indicates the importance of the CO group in the amide or surrogate linkage at 11-12 and 12-13 positions in the receptor binding process.
Description:Supplementary Material Available: lH NMR data for compounds 1-10 and 13C NMR data for compound 15 (2 pages). Ordering information is given on any current masthead page.
Publisher version (URL):http://pubs.acs.org/toc/jmcmar/38/6
E-ISSNmetadata.dc.identifier.doi = DOI:1520-4804
Appears in Collections:(CENQUIOR) Artículos

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