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Thiols and mercaptans

15 articles

2-Mercaptoethanol

2-Mercaptoethanol (β-mercaptoethanol, BME, or thioglycol; HSCH2CH2OH) is a clear, foul-smelling organosulfur liquid used chiefly to reduce disulfide bonds in proteins, notably in SDS-PAGE buffers, and to support lymphocyte growth in cell culture.

Dimercaprol

Dimercaprol, also known as British anti-Lewisite (BAL), is a dithiol chelating agent, 2,3-dimercapto-1-propanol, used to treat poisoning by arsenic, gold, inorganic mercury, and, with edetate calcium disodium, acute lead poisoning.

Dithiothreitol

Dithiothreitol (DTT), also called Cleland's reagent, is a dithiol reducing agent introduced by W. W. Cleland in 1964 to reduce disulfide bonds and keep thiol groups reduced.

Ethanethiol

Ethanethiol, commonly called ethyl mercaptan, is the sulfur analog of ethanol, a flammable liquid boiling near 35 °C with a skunk-like odor detectable at about 1 ppbv.

Gold-containing drugs

Gold-containing drugs, also known as gold salts, are medicines in which gold is the active component; chrysotherapy for rheumatoid arthritis used injectable gold thiolates and oral auranofin.

Methanethiol

Methanethiol (CH3SH), also called methyl mercaptan, is the simplest thiol, a colorless, highly flammable gas smelling of rotten cabbage, detectable at about one part per billion.

Sulfenic acid

Sulfenic acids, organosulfur oxyacids of formula R–SOH, are highly reactive intermediates in thiol oxidation, formed on cysteine in proteins and during the cutting of onions and garlic.

Thiol

Thiols, formerly known as mercaptans, are organosulfur compounds of structure RSH, the sulfur analogs of alcohols, with strong skunky odors and a role in natural gas odorization.

Thiol properties and synthesis

Thiols, also called mercaptans, are organosulfur compounds of the form R–S–H, the sulfur analogs of alcohols; they are more acidic than alcohols and oxidize first to disulfides.

Thiol-ene reaction

The thiol-ene reaction is the radical-mediated addition of a thiol across a carbon-carbon double bond, typically giving an anti-Markovnikov thioether; it is classed as a click reaction and used in coatings, adhesives, and 3D printing.

Thiol-mediated hydrogen atom transfer cocatalysis

Thiol-mediated hydrogen atom transfer cocatalysis is a radical catalysis mode in which a thiol cocatalyst, acting through its thiyl radical, shuttles hydrogen atoms while a photoredox or metal catalyst generates radical intermediates.

Thiol–disulfide exchange

Thiol–disulfide exchange, also called thiol–disulfide interchange, is the reaction in which a thiolate anion attacks a disulfide's sulfur atom, breaking one S–S bond and forming a new one, transferring the linkage.

Thiolate-protected gold cluster

A thiolate-protected gold cluster is an atomically precise particle of gold, formula Aun(SR)m, whose gold core below about 2 nm is stabilized by thiolate ligands and behaves molecularly.

Thiophenol

Thiophenol, also known as benzenethiol or phenyl mercaptan, is the simplest aromatic thiol, a foul-smelling, highly toxic liquid used mainly as an intermediate for pesticides, pharmaceuticals, and amber dyes.

Transition metal thiolate complex

A transition metal thiolate complex, also called a metal thiolate complex, is a coordination compound with strongly covalent metal-sulfur bonds, found in iron-sulfur enzymes, metallothioneins, and pincer-ligated catalysts.