Synthesis and biological activity of novel backbone‐bicyclic Substance‐P analogs containing lactam and disulfide bridges
- 1 May 1997
- journal article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 49 (5) , 421-426
- https://doi.org/10.1111/j.1399-3011.1997.tb00894.x
Abstract
A biased library of 60 novel backbone‐bicyclic Substance P analogs was prepared by the simultaneous multiple peptide synthesis method. The peptides, containing both a lactam and a disulfide ring, were synthesized by combined Boc and Fmoc chemistries, and were cyclized on the resin. Cleavage of the S‐benzyl group and oxidation of the sulfhydryl groups was enabled by adaptation of the diphenylsulfoxide‐trichloromethylsilane method to solid‐phase synthesis. The peptides were screened for NK‐1 and NK‐3 activity, and were found to be weak agonists. © Munksgaard 1997.Keywords
This publication has 17 references indexed in Scilit:
- Backbone Cyclization of the C‐terminal Part of Substance P. Part 1: The Important Role of the Sulphur in Position 11Journal of Peptide Science, 1996
- Synthesis and Biological Activity of NK-1 Selective, N-Backbone Cyclic Analogs of the C-Terminal Hexapeptide of Substance PJournal of Medicinal Chemistry, 1996
- Synthesis of peptide amides using Fmoc‐based solid‐phase procedures on 4‐methylbenzhydrylamine resinsInternational Journal of Peptide and Protein Research, 1995
- Nmr and molecular modeling investigations of the neuropeptide substance P in the presence of 15 mM sodium dodecyl sulfate micellesBiopolymers, 1994
- Comparison of the Conformation of Active and Nonactive Backbone Cyclic Analogs of Substance P as a Tool To Elucidate Features of the Bioactive Conformation: NMR and Molecular Dynamics in DMSO and WaterJournal of Medicinal Chemistry, 1994
- Total synthesis of human insulin by regioselective disulfide formation using the silyl chloride-sulfoxide methodJournal of the American Chemical Society, 1993
- Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide unitsThe Journal of Organic Chemistry, 1992
- Conformation of cyclic analogs of substance P: NMR and molecular dynamics in dimethyl sulfoxideJournal of the American Chemical Society, 1992
- Backbone cyclization: A new method for conferring conformational constraint on peptidesBiopolymers, 1991
- Preferential conformation of substance P in solutionEuropean Journal of Biochemistry, 1986