Organic disulfides

Cystine is the oxidized derivative of the amino acid cysteine and has the formula (SCH2CH(NH2)CO2H)2. It is a white solid that is poorly soluble in water. As a residue in proteins, cystine serves two functions: a site of redox reactions and a mechanical linkage that allows proteins to retain their three-dimensional structure.

pair of enantiomers

In chemistry, a disulfide (or disulphide in British English) is a compound containing a functional group or the anion. In inorganic chemistry, the anion appears in a few rare minerals. Compounds of the form are usually called persulfides instead.

chemical compound

chemical compound

chemical compound

Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is the functional form of lipoic acid, i.e the carboxyl group is attached to protein via an amine with an amide linkage. Illustrative of the biochemical role of lipoamide is in the conversion of pyruvate to acetyl lipoamide.

chemical compound

Ajoene is an organosulfur compound found in garlic (Allium sativum) extracts. It is a colorless liquid that contains sulfoxide and disulfide functional groups. The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four stereoisomers, which differ in terms of the stereochemistry of the central alkene (E- vs Z-) and the chirality of the sulfoxide sulfur (R- vs S-).

chemical compound

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of th

Lenthionine is an organosulfur compound with the formula . The compound consists of a 1,4- ring (pentathiepane). Lenthionine is a major component of the organosulfur compounds found in shiitake mushrooms (Lentinula edodes). onions, and garlic, and it is partly responsible for their flavor. The mechanism of its formation is unclear, but it likely involves the enzyme C–S lyase.

Pyritinol also called pyridoxine disulfide or pyrithioxine (European drug names Encephabol, Encefabol, Cerbon 6) is a semi-synthetic water-soluble analog of vitamin B6 (Pyridoxine HCl). It was produced in 1961 by Merck Laboratories by bonding 2 vitamin B6 compounds (pyridoxine) together with a disulfide bridge. Since the 1970s, it has been a prescription and OTC drug in several countries for cognitive disorders, rheumatoid arthritis, and learning disorders in children. Since the early 1990s it has been sold as a nootropic dietary supplement in the United States.

chemical compound

Sulbutiamine sold under the brand names Arcalion, Enerion, and Sulbuxin is a synthetic derivative of thiamine (vitamin B1). In France, it is used to treat symptoms of weakness or fatigue. In Uruguay, it is prescribed when there is thiamine deficiency, mainly in patients with asthenia, overwork, apathy, depressive states, memory disorders, and iatrogenic disorders of wakefulness. It is also sold as a dietary supplement. Sulbutiamine was discovered in Japan as part of an effort to develop useful thiamine derivatives.

Cystamine ('''2,2'-dithiobisethanamine''') is an organic disulfide. It is formed when cystine is heated, the result of decarboxylation. Cystamine is an unstable liquid and is generally handled as the dihydrochloride salt, C4H12N2S2·2HCl, which is stable to 203-214 °C at which point it decomposes. Cystamine is toxic if swallowed or inhaled and potentially harmful by contact.

Pantethine (bis-pantethine or co-enzyme pantethine) is a dimeric form of pantetheine, which is produced from pantothenic acid (vitamin B5) by the addition of cysteamine. Pantethine was discovered by Gene Brown, a PhD student at the time. Pantethine is two molecules of pantetheine linked by a disulfide bridge. Pantetheine is an intermediate in the production of coenzyme A by the body. Most vitamin B5 supplements are in the form of calcium pantothenate, a salt of pantothenic acid, with doses in the range of 5 to 10 mg/day. In contrast, pantethine is sold as a dietary supplement for lowering

Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a dithiolene complex. 3,4-Bis(trifluoromethyl)-1,2-dithiete is a particularly stable example.

Fursultiamine (INN; chemical name thiamine tetrahydrofurfuryl disulfide or TTFD; brand names Adventan, Alinamin-F, Benlipoid, Bevitol Lipophil, Judolor, Lipothiamine) is a medication and vitamin used to treat thiamine deficiency. Chemically, it is a disulfide derivative of thiamine and is similar in structure to allithiamine.

2,2′-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating carboxylic acid for coupling reactions, as in the following reaction: 600px

chemical compound

Prosultiamine (INN; also known as thiamine propyl disulfide or TPD; brand name Jubedel,) is a disulfide thiamine derivative discovered in garlic in Japan in the 1950s, and is similar to allithiamine. It was developed as a treatment for vitamin B1 deficiency. It has improved lipid solubility relative to thiamine and is not rate-limited by dependency on intestinal transporters for absorption, hence the reasoning for its development.

Allithiamine (thiamine allyl disulfide or TAD) is a lipid-soluble form of vitamin B1 which was discovered in garlic (Allium sativum) in the 1950s along with its homolog prosultiamine. They were both investigated for their ability to treat Wernicke–Korsakoff syndrome and beriberi better than thiamine.

Homocystine is the organosulfur compound with the formula . It is disulfide derived from oxidation of homocysteine. Its relationship with homocysteine is analogous to the relationship between cystine and cysteine.