Pseudopeptides with a centrally positioned alkene-based disulphide bridge mimetic stimulate kallikrein-related peptidase 3 activityElectronic supplementary information (ESI) available. See DOI: 10.1039/c3md20292e

Pseudopeptides based on the kallikrein-related peptidase 3 (KLK3) activating bicyclic peptide "C-4" comprising hydrocarbon-based disulphide bridge mimetics have been synthesized. After investigating different synthetic approaches, the pseudopeptides were successfully cyclized from two l -a...

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Hauptverfasser: Meinander, Kristian, Weisell, Janne, Pakkala, Miikka, Tadd, Andrew C, Hekim, Can, Kallionpää, Roope, Widell, Kim, Stenman, Ulf-Håkan, Koistinen, Hannu, Närvänen, Ale, Vepsäläinen, Jouko, Luthman, Kristina, Wallén, Erik A. A
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creator Meinander, Kristian
Weisell, Janne
Pakkala, Miikka
Tadd, Andrew C
Hekim, Can
Kallionpää, Roope
Widell, Kim
Stenman, Ulf-Håkan
Koistinen, Hannu
Närvänen, Ale
Vepsäläinen, Jouko
Luthman, Kristina
Wallén, Erik A. A
description Pseudopeptides based on the kallikrein-related peptidase 3 (KLK3) activating bicyclic peptide "C-4" comprising hydrocarbon-based disulphide bridge mimetics have been synthesized. After investigating different synthetic approaches, the pseudopeptides were successfully cyclized from two l -allylglycine side chains via an alkene ring-closing metathesis reaction during the peptide synthesis. The alkene-linker was formed in a 1 : 1 E / Z isomer ratio. The resulting pseudopeptides were almost as potent as the parent peptide, increasing the activity of KLK3 over four-fold at 200 μg ml −1 (130-140 μM) concentrations. First successful pseudopeptides of the KLK3-activating bicyclic peptide "C-4" are reported.
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title Pseudopeptides with a centrally positioned alkene-based disulphide bridge mimetic stimulate kallikrein-related peptidase 3 activityElectronic supplementary information (ESI) available. See DOI: 10.1039/c3md20292e
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