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2-Mercaptoethanol

 

 
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2-Mercaptoethanol
 
 
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2-Mercaptoethanol (also ß-mercaptoethanol, or "2BME") is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HOCH2CH2SH. It is a hybrid of ethylene glycol
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
, HOCH2CH2OH, and 1,2-ethanedithiol
1,2-Ethanedithiol

1,2-Ethanedithiol is an odorous, colorless liquid with the formula C2H42. It is a common building block in organic synthesis and an excellent ligand for metal ions....
, HSCH2CH2SH. ME or ßME, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
 by scavenging hydroxyl radicals (amongst others) . It is widely used because the hydroxyl group confers solubility in water and lowers the volatility.






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2-Mercaptoethanol (also ß-mercaptoethanol, or "2BME") is the chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 HOCH2CH2SH. It is a hybrid of ethylene glycol
Ethylene glycol

Ethylene glycol is an alcohol with two -OH groups , a chemical compound widely used as an automobile antifreeze. In its pure form, it is an odorless, colorless, syrupy, sweet tasting, toxic liquid....
, HOCH2CH2OH, and 1,2-ethanedithiol
1,2-Ethanedithiol

1,2-Ethanedithiol is an odorous, colorless liquid with the formula C2H42. It is a common building block in organic synthesis and an excellent ligand for metal ions....
, HSCH2CH2SH. ME or ßME, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant
Antioxidant

An antioxidant is a molecule capable of slowing or preventing the Redox of other molecules. Oxidation is a chemical reaction that transfers electrons from a substance to an oxidizing agent....
 by scavenging hydroxyl radicals (amongst others) . It is widely used because the hydroxyl group confers solubility in water and lowers the volatility. Due to its diminished vapor pressure, its odour, while unpleasant, is less objectionable than related thiol
Thiol

In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur atom and a hydrogen atom . Being the sulfur analogue of an alcohol group , this functional group is referred to either as a thiol group or a sulfhydryl group....
s.

Preparation

ME may be prepared by the action of hydrogen sulfide
Hydrogen sulfide

Hydrogen sulfide is the chemical compound with the chemical formula Hydrogen2Sulfur. This colorless, toxic and flammable gas is partially responsible for the foul odor of egg and flatulence....
 on ethylene oxide
Ethylene oxide

Ethylene oxide is the organic compound with the chemical formula C2H4O. This colorless flammable gas with a faintly sweet odor is the simplest epoxide, a three-membered ring consisting of two carbon and one oxygen atom....
:


Reactions

2-Mercaptoethanol reacts with aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s and ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s to give the corresponding oxathiolanes. This makes 2-mercaptoethanol useful as a protecting group
Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction....
.


Applications


Denaturing proteins

Some proteins can be denatured by 2-mercaptoethanol via its ability to cleave disulfide bonds:
cys
Cystine

Cystine is the amino acid dimer formed when a pair of cysteine molecules are joined by a disulfide bond. It is described by the formula 2....
S-Scys + 2 HOCH2CH2SH ? 2 cysSH
Cysteine

Cysteine is an a-amino acid with the chemical formula HO2CCHCH2SH. It is a non-essential amino acid, which means that humans can synthesize it....
  + HOCH2CH2S-SCH2CH2OH


By breaking the S-S bonds, both the tertiary structure
Tertiary structure

In biochemistry and chemistry, the tertiary structure of a protein or any other macromolecule is its three-dimensional structure, as defined by the atomic coordinates....
 and the quaternary structure
Quaternary structure

In biochemistry, quaternary structure is the arrangement of multiple protein folding protein molecules in a multi-subunit complex....
 of some proteins can be disrupted. Because of its ability to disrupt the structure of proteins, it is used in the analysis of proteins, for instance, to ensure that a protein solution contains monomeric protein molecules, instead of disulfide linked dimers or higher order oligomers.

2-Mercaptoethanol is often used interchangeably with dithiothreitol
Dithiothreitol

Dithiothreitol is the common name for a small-molecule redox reagent known as Cleland's reagent. DTT's formula is C4H10O2S2 and the molecular structure of its reduced form is shown at the right; its oxidized form is a disulfide bond 6-membered ring ....
 (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP
TCEP

TCEP is a reducing agent frequently used in biochemistry and molecular biology applications. It is often prepared and used as a hydrochloride salt....
) in biological applications.

Denaturing Ribonucleases

2-Mercaptoethanol is used in some RNA isolation procedures to eliminate ribonuclease
Ribonuclease

Ribonuclease is a type of nuclease that catalysis the degradation of RNA into smaller components. Ribonucleases can be divided into endoribonucleases and exoribonucleases, and comprise several sub-classes within the EC 2.7 and 3.1 classes of enzymes....
 released during cell lysis. Numerous disulfide bonds make ribonucleases very stable enzymes, so 2-mercaptoethanol is used to reduce these disulfide bonds and irreversibly denature the proteins. This prevent them from digesting the RNA during the procedure.

Safety

2-Mercaptoethanol is considered a "severe" poison, causing irritation to the nasal passageways and respiratory tract upon inhalation, vomiting and stomach pain through ingestion, and potentially fatal absorption if it contacts the skin.