Highly Stable Meldrum’s Acid Derivatives for Irreversible Aqueous Covalent Modification of Amines

Highly Stable Meldrum’s Acid Derivatives for Irreversible Aqueous Covalent Modification of Amines

This work describes the development of a highly stable and pH-responsive probe for lysine modification. The scaffold has marked stability in the presence of several biological nucleophiles and across a wide pH range (2–12). Several functional analogs showed robust labeling of a protein at pH > 9....

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (7), p.2626-2629
Hauptverfasser: Davis, Garrett J, Sofka, Holly A, Jewett, John C
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Dioxanes - chemistry
Hydrogen-Ion Concentration
Lysine - chemistry
Molecular Structure
Water - chemistry
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container_title Organic letters
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creator Davis, Garrett J
Sofka, Holly A
Jewett, John C
description This work describes the development of a highly stable and pH-responsive probe for lysine modification. The scaffold has marked stability in the presence of several biological nucleophiles and across a wide pH range (2–12). Several functional analogs showed robust labeling of a protein at pH > 9. Taken together, our system displays versatility and can be easily adapted for variety of applications, while demonstrating stability suitable for a wide range of biologically compatible systems.
doi_str_mv 10.1021/acs.orglett.0c00597
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source MEDLINE; American Chemical Society Journals
subjects Amines - chemistry
Dioxanes - chemistry
Hydrogen-Ion Concentration
Lysine - chemistry
Molecular Structure
Water - chemistry
title Highly Stable Meldrum’s Acid Derivatives for Irreversible Aqueous Covalent Modification of Amines
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