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Title: 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
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.
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ISSN: 0022-2623
???metadata.dc.identifier.doi???: 10.1021/jm00006a021
Citation: Journal of Medicinal Chemistry 38 : 1015-1021 (1995)
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