2-Mercaptoethanol (also β-mercaptoethanol, BME, 2BME, 2-ME or β-met) is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...

with the formula HOCH₂CH₂SH. ME or βME, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant 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 odor, while unpleasant, is less objectionable than related thiols.

Production

2-Mercaptoethanol is manufactured industrially by the reaction of ethylene oxide with

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The und ...

. Thiodiglycol and various zeolites catalyze the reaction. : Industrial synthesis of mercaptoethanol

Reactions

2-Mercaptoethanol reacts with

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...

s and

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...

s to give the corresponding oxathiolanes. This makes 2-mercaptoethanol useful as a protecting group, giving a derivative whose stability is between that of a dioxolane and a

dithiolane A dithiolane is a sulfur heterocycle derived from cyclopentane by replacing two methylene bridges (-- units) with thioether groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane. 1,2-Dithiolanes are cyclic disulfides. Some dithi ...

. :

Oxathiolane-formation-with-2-mercaptoethanol-2D-skeletal

Applications

Reducing proteins

Some proteins can be denatured by 2-mercaptoethanol, which cleaves the disulfide bonds that may form between thiol groups of

cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, s ...

residues. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right: : RS–SR + 2 HOCH₂CH₂SH 2 RSH + HOCH₂CH₂S–SCH₂CH₂OH : 2-Mercaptoethanol Breaks Disulfide Bonds

2-Mercaptoethanol Breaks Disulfide Bonds

By breaking the S-S bonds, both the

tertiary structure Protein tertiary structure is the three dimensional shape of a protein. The tertiary structure will have a single polypeptide chain "backbone" with one or more protein secondary structures, the protein domains. Amino acid side chains may int ...

and the quaternary structure of some proteins can be disrupted. Because of its ability to disrupt the structure of proteins, it was 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. However, since 2-mercaptoethanol forms adducts with free cysteines and is somewhat more toxic, dithiothreitol (DTT) is generally more used especially in SDS-PAGE. DTT is also a more powerful reducing agent with a redox potential (at pH 7) of −0.33 V, compared to −0.26 V for 2-mercaptoethanol. 2-Mercaptoethanol is often used interchangeably with dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP) in biological applications. Although 2-mercaptoethanol has a higher volatility than DTT, it is more stable: 2-mercaptoethanol's

half-life Half-life (symbol ) is the time required for a quantity (of substance) to reduce to half of its initial value. The term is commonly used in nuclear physics to describe how quickly unstable atoms undergo radioactive decay or how long stable at ...

is more than 100 hours at pH 6.5 and 4 hours at pH 8.5; DTT's half-life is 40 hours at pH 6.5 and 1.5 hours at pH 8.5.

Preventing protein oxidation

2-Mercaptoethanol and related reducing agents (e.g., DTT) are often included in enzymatic reactions to inhibit the oxidation of free sulfhydryl residues, and hence maintain protein activity. It is often used in enzyme assays as a standard buffer component.

Denaturing ribonucleases

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

ribonuclease Ribonuclease (commonly abbreviated RNase) is a type of nuclease that catalyzes the degradation of RNA into smaller components. Ribonucleases can be divided into endoribonucleases and exoribonucleases, and comprise several sub-classes within t ...

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 prevents them from digesting the RNA during its extraction procedure.

Deprotecting carbamates

Some carbamate protecting groups such as carboxybenzyl (Cbz) or allyloxycarbonyl (alloc) can be deprotected using 2-mercaptoethanol in the presence of potassium phosphate in dimethylacetamide.

Safety

2-Mercaptoethanol is considered toxic, causing irritation to the nasal passageways and respiratory tract upon inhalation, irritation to the skin, vomiting and stomach pain through ingestion, and potentially death if severe exposure occurs.

References

{{DEFAULTSORT:Mercaptoethanol, 2- Thiols Primary alcohols Reducing agents Foul-smelling chemicals