N-Ethylmaleimide: Difference between revisions

Latest revision as of 03:44, 13 February 2025

Overview[edit]

N-Ethylmaleimide (NEM) is an organic compound that is widely used in biochemical research. It is a derivative of maleimide and is known for its ability to modify thiol groups in proteins and other molecules. This property makes it a valuable tool in the study of protein structure and function.

Chemical Properties[edit]

N-Ethylmaleimide is a small molecule with the chemical formula C₆H₇NO₂. It is a white crystalline solid that is soluble in organic solvents. The compound is characterized by the presence of a reactive maleimide group, which can form covalent bonds with thiol groups in proteins.

Mechanism of Action[edit]

N-Ethylmaleimide acts by alkylating thiol groups in proteins. The maleimide group in NEM reacts with the sulfhydryl group (-SH) of cysteine residues, forming a stable thioether bond. This reaction is often used to block or modify the function of proteins by preventing the formation of disulfide bonds or by altering the protein's conformation.

Applications in Research[edit]

N-Ethylmaleimide is used in a variety of biochemical and molecular biology applications. It is commonly employed to:

Inhibit enzyme activity by modifying active site cysteine residues.
Study protein folding and stability by preventing disulfide bond formation.
Investigate signal transduction pathways by modifying key cysteine residues in signaling proteins.

Safety and Handling[edit]

N-Ethylmaleimide is a hazardous chemical and should be handled with care. It is an irritant and can cause skin and eye irritation. Proper protective equipment, such as gloves and goggles, should be used when handling NEM.

Related Pages[edit]

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-'''N-Ethylmaleimide''' ('''NEM''') is a [[organic compound]] that is derived from [[maleic anhydride]]. It is a reagent used in [[biochemistry]] and [[molecular biology]] applications. It is a clear, colorless liquid that is soluble in water, ethanol, and acetone.
+{{DISPLAYTITLE:N-Ethylmaleimide}}
-== Structure and Properties ==
+== Overview ==
-N-Ethylmaleimide has the molecular formula C6H7NO2. It is a derivative of maleic anhydride, with an ethyl group replacing one of the hydrogen atoms in the imide group. This gives NEM its unique properties, including its reactivity with [[thiol]] groups.
+[[File:NEMmech.jpg|thumb|right|Mechanism of action of N-Ethylmaleimide]]
+'''N-Ethylmaleimide''' (NEM) is an organic compound that is widely used in biochemical research. It is a derivative of maleimide and is known for its ability to modify thiol groups in proteins and other molecules. This property makes it a valuable tool in the study of protein structure and function.
-== Uses ==
+== Chemical Properties ==
-N-Ethylmaleimide is primarily used as a reagent in biochemistry and molecular biology. It is particularly useful for its ability to irreversibly inhibit [[enzyme]]s that have a critical cysteine residue. This is due to its reactivity with thiol groups, which allows it to form a stable covalent bond with the cysteine residue, effectively blocking its activity.
+N-Ethylmaleimide is a small molecule with the chemical formula C<sub>6</sub>H<sub>7</sub>NO<sub>2</sub>. It is a white crystalline solid that is soluble in organic solvents. The compound is characterized by the presence of a reactive maleimide group, which can form covalent bonds with thiol groups in proteins.
-In addition to its use in enzyme inhibition, NEM is also used in the study of [[protein]] structure and function. It can be used to label and identify cysteine residues in proteins, providing valuable information about the protein's structure and how it interacts with other molecules.
+== Mechanism of Action ==
+N-Ethylmaleimide acts by alkylating thiol groups in proteins. The maleimide group in NEM reacts with the sulfhydryl group (-SH) of cysteine residues, forming a stable thioether bond. This reaction is often used to block or modify the function of proteins by preventing the formation of disulfide bonds or by altering the protein's conformation.
-== Safety ==
+== Applications in Research ==
-N-Ethylmaleimide is considered a hazardous substance. It can cause skin and eye irritation, and may be harmful if swallowed or inhaled. Proper safety precautions should be taken when handling this substance, including the use of personal protective equipment and adequate ventilation.
+N-Ethylmaleimide is used in a variety of biochemical and molecular biology applications. It is commonly employed to:
-== See Also ==
+* Inhibit [[enzyme]] activity by modifying active site cysteine residues.
-* [[Maleic anhydride]]
+* Study [[protein folding]] and stability by preventing disulfide bond formation.
-* [[Biochemistry]]
+* Investigate [[signal transduction]] pathways by modifying key cysteine residues in signaling proteins.
-* [[Molecular biology]]
+== Safety and Handling ==
+N-Ethylmaleimide is a hazardous chemical and should be handled with care. It is an irritant and can cause skin and eye irritation. Proper protective equipment, such as gloves and goggles, should be used when handling NEM.
+== Related Pages ==
+* [[Maleimide]]
+* [[Thiol]]
+* [[Protein structure]]
 * [[Enzyme inhibition]]
 [[Category:Organic compounds]]
-[[Category:Biochemistry reagents]]
+[[Category:Biochemistry]]
-[[Category:Molecular biology]]
-{{chemistry-stub}}
-{{medicine-stub}}