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Hub AI
Disulfide AI simulator
(@Disulfide_simulator)
Hub AI
Disulfide AI simulator
(@Disulfide_simulator)
Disulfide
In chemistry, a disulfide (or disulphide in British English) is a compound containing a R−S−S−R′ functional group or the S2−
2 anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups.
In inorganic chemistry, the anion appears in a few rare minerals, but the functional group has tremendous importance in biochemistry. Disulfide bridges formed between thiol groups in two cysteine residues are an important component of the tertiary and quaternary structure of proteins.
Compounds of the form R−S−S−H are usually called persulfides instead.
Disulfides have a C–S–S–C dihedral angle approaching 90°. The S–S bond length is 2.03 Å in diphenyl disulfide, similar to that in elemental sulfur.
Disulfides are usually symmetric but they can also be unsymmetric. Symmetrical disulfides are compounds of the formula RSSR. Most disulfides encountered in organosulfur chemistry are symmetrical disulfides. Unsymmetrical disulfides (also called heterodisulfides or mixed disulfides) are compounds of the formula RSSR'. Unsymmetrical disulfide are less common in organic chemistry, but many disulfides in nature are unsymmetrical.
An important symmetric disulfide is cystine. In the disorder cystinosis results from crystallization of cystine, the poorly soluble oxidized dimer of the amino acid cysteine. When sufferers of this disease are treat with cysteamine, the excessive cystine is removed. Cysteamine functions by the converting the symmetrical disulfide cystine to a more soluble mixed disulfide and cysteine:
The conversion is an example of thiol-disulfide exchange, which is discussed below.
Disulfides can be components of rings. Lipoic acid, a 1,2-dithiolane is a major example. Rings with more than one disulfide usually tend to polymerize.
Disulfide
In chemistry, a disulfide (or disulphide in British English) is a compound containing a R−S−S−R′ functional group or the S2−
2 anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups.
In inorganic chemistry, the anion appears in a few rare minerals, but the functional group has tremendous importance in biochemistry. Disulfide bridges formed between thiol groups in two cysteine residues are an important component of the tertiary and quaternary structure of proteins.
Compounds of the form R−S−S−H are usually called persulfides instead.
Disulfides have a C–S–S–C dihedral angle approaching 90°. The S–S bond length is 2.03 Å in diphenyl disulfide, similar to that in elemental sulfur.
Disulfides are usually symmetric but they can also be unsymmetric. Symmetrical disulfides are compounds of the formula RSSR. Most disulfides encountered in organosulfur chemistry are symmetrical disulfides. Unsymmetrical disulfides (also called heterodisulfides or mixed disulfides) are compounds of the formula RSSR'. Unsymmetrical disulfide are less common in organic chemistry, but many disulfides in nature are unsymmetrical.
An important symmetric disulfide is cystine. In the disorder cystinosis results from crystallization of cystine, the poorly soluble oxidized dimer of the amino acid cysteine. When sufferers of this disease are treat with cysteamine, the excessive cystine is removed. Cysteamine functions by the converting the symmetrical disulfide cystine to a more soluble mixed disulfide and cysteine:
The conversion is an example of thiol-disulfide exchange, which is discussed below.
Disulfides can be components of rings. Lipoic acid, a 1,2-dithiolane is a major example. Rings with more than one disulfide usually tend to polymerize.