Photo‐claisen rearrangement in a coumarin‐caged peptide leads to a surprising enzyme hyperactivation
Abstract: Protein phosphatase-1 (PP1) is a ubiquitous enzyme that counteracts hundreds of kinases in cells. PP1 interacts with regulatory proteins via an RVxF peptide motif that binds to a hydrophobic groove on the enzyme. PP1-disrupting peptides (PDPs) compete with these regulatory proteins, leading to the release of the active PP1 subunit and promoting substrate dephosphorylation. Building on previous strategies employing the ortho-nitrobenzyl (o-Nb) group as a photocage to control PDP activity, we introduced coumarin derivatives into a PDP via an ether bond to explore their effects on PP1 activity. Surprisingly, our study revealed that the coumarin-caged peptides (PDP-DEACM and PDP-CM) underwent a photo-Claisen rearrangement, resulting in an unexpected hyperactivation of PP1. Our findings underscore the importance of linker design in controlling uncaging efficiency of photocages and highlight the need for comprehensive in vitro analysis before cellular experiments
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Anmerkungen
-
ChemBioChem. - 25, 22 (2024) , e202400561, ISSN: 1439-7633
- Ereignis
-
Veröffentlichung
- (wo)
-
Freiburg
- (wer)
-
Universität
- (wann)
-
2024
- Urheber
- DOI
-
10.1002/cbic.202400561
- URN
-
urn:nbn:de:bsz:25-freidok-2608558
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:21 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Maller, Corina
- Marouda, Eirini
- Köhn, Maja
- Universität
Entstanden
- 2024
Ähnliche Objekte (12)
Photo‐Claisen Rearrangement in a Coumarin‐Caged Peptide Leads to a Surprising Enzyme Hyperactivation
Immobilisierungsstrategien zur Herstellung von Peptid- und Wirkstoff-Arrays und deren Anwendung
Interpreting the Activity of Metastasis-Promoting PRL-3 Through the Total Synthesis of Phosphatidylinositol Analogues
Exploring uncharted territory : : toward metabolite network maps
Miklós Bodanszky Award Lecture: Advances in the selective targeting of protein phosphatase-1 and phosphatase-2A with peptides
Regulatory mechanisms of phosphatase of regenerating liver (PRL)-3
Prediction and verification of novel peptide targets of protein tyrosine phosphatase 1B
Chromatic Selectivity of Coumarin‐Caged Oligonucleotides
Chromatic selectivity of coumarin-caged oligonucleotides
A modular approach for the synthesis of diverse heterobifunctional cyanine dyes
Microcystins: Synthesis and structure–activity relationship studies toward PP1 and PP2A
The human DEPhOsphorylation Database DEPOD: 2019 update
Photo‐Claisen Rearrangement in a Coumarin‐Caged Peptide Leads to a Surprising Enzyme Hyperactivation
Immobilisierungsstrategien zur Herstellung von Peptid- und Wirkstoff-Arrays und deren Anwendung
Interpreting the Activity of Metastasis-Promoting PRL-3 Through the Total Synthesis of Phosphatidylinositol Analogues
Exploring uncharted territory : : toward metabolite network maps
Miklós Bodanszky Award Lecture: Advances in the selective targeting of protein phosphatase-1 and phosphatase-2A with peptides
Regulatory mechanisms of phosphatase of regenerating liver (PRL)-3
Prediction and verification of novel peptide targets of protein tyrosine phosphatase 1B
Chromatic Selectivity of Coumarin‐Caged Oligonucleotides
Chromatic selectivity of coumarin-caged oligonucleotides
A modular approach for the synthesis of diverse heterobifunctional cyanine dyes
Microcystins: Synthesis and structure–activity relationship studies toward PP1 and PP2A
The human DEPhOsphorylation Database DEPOD: 2019 update
Photo‐Claisen Rearrangement in a Coumarin‐Caged Peptide Leads to a Surprising Enzyme Hyperactivation
Immobilisierungsstrategien zur Herstellung von Peptid- und Wirkstoff-Arrays und deren Anwendung
Interpreting the Activity of Metastasis-Promoting PRL-3 Through the Total Synthesis of Phosphatidylinositol Analogues
Exploring uncharted territory : : toward metabolite network maps
Miklós Bodanszky Award Lecture: Advances in the selective targeting of protein phosphatase-1 and phosphatase-2A with peptides
Regulatory mechanisms of phosphatase of regenerating liver (PRL)-3
Prediction and verification of novel peptide targets of protein tyrosine phosphatase 1B
Chromatic Selectivity of Coumarin‐Caged Oligonucleotides
Chromatic selectivity of coumarin-caged oligonucleotides
A modular approach for the synthesis of diverse heterobifunctional cyanine dyes
Microcystins: Synthesis and structure–activity relationship studies toward PP1 and PP2A