disulfide
Quick Summary
A disulfide is a chemical compound containing two sulfur atoms. These can be inorganic or organic, with organic disulfides featuring a divalent group of two sulfur atoms (SS) bonded to organic radicals. A unique property of sulfur is its ability to form chains of sulfur atoms with organic groups at either end, denoted as RSnRā², where n represents the number of sulfur atoms, with disulfides having n=2.12
Disulfides play crucial roles in biological systems. For instance, the amino acid cystine, a disulfide, is vital for protein structure and function. The interconversion between cysteine and cystine disulfide groups is important in cell membrane transport, immune responses, and blood clotting. Hair waving processes involve the temporary cleavage and reformation of these disulfide bonds in keratin. Lipoic acid, a cyclic disulfide, acts as a coenzyme involved in various metabolic processes and biological oxidations.2
Disulfides are generally prepared by oxidizing thiols. They can also be reduced back to thiols, a process essential in biochemistry. Disulfides can undergo further oxidation to form sulfoxides, sulfones, and sulfonic acids. Some disulfides are known for their distinct flavors and aromas, contributing to the taste of foods like shiitake mushrooms, beer, and wine, as well as the characteristic smell of garlic.32
Ask Britannica AI about this topic
Britannica doesn't have a full article on this topic, so we've curated a list of our relevant coverage.
organosulfur compoundThe sulfur atombetween peroxides (RāOOāR), disulfides (RāSSāR), and diselenides (RāSeSeāR), and between oxonium (R3O+), sulfonium (R3S+), and selenonium salts (R3Se+), where R represents a general carbon groupāe.g., the methyl group, CH3, or the ethyl group, C2H5.
Read Morebetween peroxides (RāOOāR), disulfides (RāSSāR), and diselenides (RāSeSeāR), and between oxonium (R3O+), sulfonium (R3S+), and selenonium salts (R3Se+), where R represents a general carbon groupāe.g., the methyl group, CH3, or the ethyl group, C2H5.
Read More
organosulfur compoundThiolsā¦of natural thiol pairs and disulfide groups constitutes a key oxidation-reduction reaction (or redox reaction) used in biochemistry; the redox potential, or tendency to attract electrons and thus become reduced, of the thiol-disulfide system is such that most disulfides are reducible by the biological reducing agent nicotinamide adenine dinucleotide (NADH),ā¦
Read Moreā¦of natural thiol pairs and disulfide groups constitutes a key oxidation-reduction reaction (or redox reaction) used in biochemistry; the redox potential, or tendency to attract electrons and thus become reduced, of the thiol-disulfide system is such that most disulfides are reducible by the biological reducing agent nicotinamide adenine dinucleotide (NADH),ā¦
Read More
organosulfur compoundReactionsOxidation of thiols initially affords disulfides, which can also be formed by the combination of thiyl radicals. Sulfenic acids, RāSOāH, can be isolated as the first-formed oxidation product from sterically hindered thiols; these react further with thiols to form disulfides. There are a number of practical applications associated with theā¦
Read MoreOxidation of thiols initially affords disulfides, which can also be formed by the combination of thiyl radicals. Sulfenic acids, RāSOāH, can be isolated as the first-formed oxidation product from sterically hindered thiols; these react further with thiols to form disulfides. There are a number of practical applications associated with theā¦
Read More