Everything about 2-mercaptoethanol totally explained
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2-Mercaptoethanol (also
β-mercaptoethanol) is the
chemical compound with the
formula HOCH
2CH
2SH. It is a hybrid of
ethylene glycol, HOCH
2CH
2OH, and
1,2-ethanedithiol, HSCH
2CH
2SH. ME or βME, as it's 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 odour, while unpleasant, is less objectionable than related
thiols.
ME is prepared by the action of
hydrogen sulfide on
ethylene oxide:
»
Biochemical properties
Proteins are denatured by 2-mercaptoethanol via its ability to cleave
disulfide bonds:
» cysS-Scys + 2 HOCH
2CH
2SH → 2
cysSH + HOCH
2CH
2S-SCH
2CH
2OH
»
By breaking the S-S bonds, both the
tertiary structure and the
quaternary structure of the protein can be disrupted. Because of its ability to disrupt the structure of proteins, it's used in the analysis of proteins.
2-Mercaptoethanol is often used interchangeably with
dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (
TCEP) in biological applications.
Biomedical consequences
2-Mercaptoethanol is one of the few chemicals that extends the maximum as well as the median life span of mice. In microgram quantities, 2-mercaptoethanol has been observed to have a number of possibly beneficial effects on laboratory mice.
Organic chemistry
ME reacts with
aldehydes and
ketones to give the corresponding oxathiolanes:
» Further Information
Get more info on '2-mercaptoethanol'.
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