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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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. |
doi_str_mv | 10.1039/c3md20292e |
format | Article |
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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.</description><identifier>ISSN: 2040-2503</identifier><identifier>EISSN: 2040-2511</identifier><identifier>DOI: 10.1039/c3md20292e</identifier><language>eng</language><creationdate>2013-02</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Meinander, Kristian</creatorcontrib><creatorcontrib>Weisell, Janne</creatorcontrib><creatorcontrib>Pakkala, Miikka</creatorcontrib><creatorcontrib>Tadd, Andrew C</creatorcontrib><creatorcontrib>Hekim, Can</creatorcontrib><creatorcontrib>Kallionpää, Roope</creatorcontrib><creatorcontrib>Widell, Kim</creatorcontrib><creatorcontrib>Stenman, Ulf-Håkan</creatorcontrib><creatorcontrib>Koistinen, Hannu</creatorcontrib><creatorcontrib>Närvänen, Ale</creatorcontrib><creatorcontrib>Vepsäläinen, Jouko</creatorcontrib><creatorcontrib>Luthman, Kristina</creatorcontrib><creatorcontrib>Wallén, Erik A. A</creatorcontrib><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</title><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.
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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.</abstract><doi>10.1039/c3md20292e</doi><tpages>5</tpages></addata></record> |
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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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