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Covalently Linked Protein Regulators

Covalently Linked Protein Regulators

Proteins can undergo many types of post-translational modifications, often in response to changes in their environment. These modifications play an important role in the function and stability of these proteins. Covalently linked molecules include functional groups, such as methyl, acetyl, and phosphate groups, and also small proteins, such as ubiquitin. There are around 200 different types of covalent regulators that have been identified.
These groups modify specific amino acids in a protein....

Protein Modifications in the RER

Protein Modifications in the RER

Modification of secretory and transmembrane proteins entering the rough ER begins in the ER lumen. These modifications aid in protein folding and stabilize the acquired tertiary structure. Protein modifications in the rough ER co-occur at different stages of protein folding.
Broadly, these modifications can be categorized into four main categories — glycosylation, formation of disulfide bonds, assembly of protein subunits, and specific proteolytic cleavages like removal of signal...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Related Experiment Video

Updated: Mar 3, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Selective Covalent Protein Modification by 4-Halopyridines through Catalysis.

Christopher L Schardon¹, Alfred Tuley², Joyce A V Er²

¹Biochemistry Graduate Program, The University of Texas, Austin, TX, 78712, USA.

Chembiochem : a European Journal of Chemical Biology

|May 5, 2017

Summary

This summary is machine-generated.

4-Halopyridines act as tunable covalent protein modifiers. Their reactivity can be switched, enabling selective targeting of specific proteins like DDAH1 for chemical probe development.

Keywords:

covalent inhibitors covalent probes enzyme inactivation halopyridines

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Area of Science:

Chemical Biology
Medicinal Chemistry

Background:

Covalent protein modifiers are crucial for chemical biology tools.
Developing selective and switchable reagents remains a challenge.

Purpose of the Study:

Investigate 4-halopyridines as selective, tunable, and switchable covalent protein modifiers.
Explore their utility in developing chemical probes.

Main Methods:

Assessed nonenzymatic reactivity of 4-chloropyridine with amino acids and thiols.
Studied inactivation of human dimethylarginine dimethylaminohydrolase-1 (DDAH1) using 4-halopyridines.
Synthesized and evaluated 2-fluoromethyl-substituted 4-chloropyridines.
Performed covalent labeling in Escherichia coli lysate.

Main Results:

4-Halopyridines exhibit switchable reactivity, tunable over orders of magnitude.
Demonstrated selective covalent modification of DDAH1 active site cysteine.
Showed modification requires folded proteins and is likely catalysis-dependent.

Conclusions:

4-Halopyridines are effective selective and switchable covalent protein modifiers.
Quiescent affinity labels offer a strategy for switchable electrophilicity in reagent design.