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
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Notes
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ChemBioChem. - 25, 22 (2024) , e202400561, ISSN: 1439-7633
- Event
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Veröffentlichung
- (where)
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Freiburg
- (who)
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Universität
- (when)
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2024
- Creator
- DOI
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10.1002/cbic.202400561
- URN
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urn:nbn:de:bsz:25-freidok-2608558
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:21 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Maller, Corina
- Marouda, Eirini
- Köhn, Maja
- Universität
Time of origin
- 2024
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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
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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
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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