Synthesis of Partially Modified Retro-Inverso Substance P Analogues and Their Biological Activity

Michael Chorev, Elie Rubini, Chaim Gilon, Uri Wormser, Zvi Selinger

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49 Scopus citations

Abstract

Partial retro-inverso modification of a single peptide bond was applied to pGlu-Phe-Phe-Gly-Leu-Met-NH2 (I), a C-terminal hexapeptide analogue of the neuropeptide substance P. Two analogues with reversed peptide bonds, between the pGlu-Phe and Phe-Gly residues, were prepared, purified and characterized. The analogue gpGlu-CRS)-mPhe-Phe-Gly-Leu-Met-NH2 (II) was devoid of either agonistic or antagonistic activity. The second pseu-dopeptide analogue, i.e., pGlu-Phe-gPhe-mGly-Leu-Met-NH2 (III), was found to be a full agonist with 22% of the potency of I in the guinea pig ileum assay.

Original languageEnglish
Pages (from-to)129-135
Number of pages7
JournalJournal of Medicinal Chemistry
Volume26
Issue number2
DOIs
StatePublished - Feb 1983

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