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• W2949854966 startingPage "2484" @default.
• W2949854966 abstract "A lactam-based peptidomimetic for the Phe7-Phe8 region of substance P has been synthesized. The synthesis used an anodic amide oxidation to selectively functionalize the C5-position of a 3-phenylproline derivative. The resulting proline derivative was coupled to a Cbz-protected phenylalanine, and an intramolecular reductive amination strategy used to convert the coupled material into a bicyclic piperazinone ring skeleton. The net result was a dipeptide building block that imbedded one of two proposed receptor bound conformations for the Phe7-Phe8 region of substance P into a bicyclic ring skeleton. The building block was then converted into a constrained substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor." @default.
• W2949854966 created "2019-06-27" @default.
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• W2949854966 date "2000-03-23" @default.
• W2949854966 modified "2023-10-18" @default.
• W2949854966 title "Conformationally Constrained Substance P Analogues: The Total Synthesis of a Constrained Peptidomimetic for the Phe⁷-Phe⁸ Region" @default.
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• W2949854966 doi "https://doi.org/10.1021/jo991649t" @default.
• W2949854966 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/10789461" @default.
• W2949854966 hasPublicationYear "2000" @default.
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