Disulfide
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Disulfide
In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In biology, disulfide bridges formed between thiol groups in two cysteine residues are an important component of the secondary and tertiary structure of proteins. '' Persulfide'' usually refers to compounds. In inorganic chemistry disulfide usually refers to the corresponding anion (−S−S−). Organic disulfides Symmetrical disulfides are compounds of the formula . Most disulfides encountered in organo sulfur chemistry are symmetrical disulfides. Unsymmetrical disulfides (also called heterodisulfides) are compounds of the formula . They are less common in organic chemistry, but most disulfides in nature are unsymmetrical. Properties The disulfide bonds are strong, with a typical bond dissociation energy of 60 kcal/mol (251&n ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. ...
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Thiol
In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl () group of an alcohol), and the word is a blend of "''thio-''" with "alcohol". Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans () or mercapto compounds, a term introduced in 1832 by William Christopher Zeise and is derived from the Latin ('capturing mercury')''Oxford American Dictionaries'' ( Mac OS X Leopard). because the thiolate group () bonds very str ...
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Pyrite
The mineral pyrite (), or iron pyrite, also known as fool's gold, is an iron sulfide with the chemical formula Fe S2 (iron (II) disulfide). Pyrite is the most abundant sulfide mineral. Pyrite's metallic luster and pale brass-yellow hue give it a superficial resemblance to gold, hence the well-known nickname of ''fool's gold''. The color has also led to the nicknames ''brass'', ''brazzle'', and ''Brazil'', primarily used to refer to pyrite found in coal. The name ''pyrite'' is derived from the Greek (), 'stone or mineral which strikes fire', in turn from (), 'fire'. In ancient Roman times, this name was applied to several types of stone that would create sparks when struck against steel; Pliny the Elder described one of them as being brassy, almost certainly a reference to what we now call pyrite. By Georgius Agricola's time, , the term had become a generic term for all of the sulfide minerals. Pyrite is usually found associated with other sulfides or oxides in quartz ...
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Dimethyl Disulfide
Dimethyl disulfide (DMDS) is an organic chemical compound with the molecular formula which is the simplest disulfide. It is a flammable liquid with an unpleasant, garlic-like odor. Occurrence Dimethyl disulfide is a widespread natural odoriferous compound emitted from many sources such as bacteria, fungi, plants and animals. It is an oxidation product of methanethiol in air. Along with dimethyl sulfide and dimethyl trisulfide it has been confirmed as volatile compounds given off by the fly-attracting plant known as dead-horse arum (''Helicodiceros muscivorus''). These flies are attracted to the odor resembling that of fetid meat, and thus help pollinate this plant. DMDS can be produced by the oxidation of methanethiol, e.g. with iodine: : Chemical reactions Important reactions include chlorination giving methanesulfenyl chloride (), methanesulfinyl chloride (), and methanesulfonyl chloride () as well as oxidation with hydrogen peroxide or peracetic acid giving the thiosulf ...
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Diphenyl Disulfide
Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound. Preparation and structure Diphenyl disulfide is usually prepared by the oxidation of thiophenol: : 2 PhSH + I2 → Ph2S2 + 2 HI Hydrogen peroxide can also be used as the oxidant. Ph2S2 is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour. Like most organic disulfides, the C–S–S–C core of Ph2S2 is non-planar with a dihedral angle approaching 85°. Reactions Ph2S2 is mainly used in organic synthesis as a source of the PhS substituent. A typical reaction entails the formation of PhS-substituted carbonyl compounds via the enolate: :RC(O)CHLiR' + Ph2S2 → RC(O)CH(SPh)R' + LiSPh Reduction Ph2S2 undergo ...
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Diphenyl Disulfide
Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound. Preparation and structure Diphenyl disulfide is usually prepared by the oxidation of thiophenol: : 2 PhSH + I2 → Ph2S2 + 2 HI Hydrogen peroxide can also be used as the oxidant. Ph2S2 is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour. Like most organic disulfides, the C–S–S–C core of Ph2S2 is non-planar with a dihedral angle approaching 85°. Reactions Ph2S2 is mainly used in organic synthesis as a source of the PhS substituent. A typical reaction entails the formation of PhS-substituted carbonyl compounds via the enolate: :RC(O)CHLiR' + Ph2S2 → RC(O)CH(SPh)R' + LiSPh Reduction Ph2S2 undergo ...
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Cystine
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. Formation and reactions Structure Cystine is the disulfide derived from the amino acid cysteine. The conversion can be viewed as an oxidation: : Cystine contains a disulfide bond, two amine groups, and two carboxylic acid groups. As for other amino acids, the amine and carboxylic acid groups exist is rapid equilibrium with the ammonium-carboxylate tautomer. The great majority of the literature concerns the ''l,l-''cystine, derived from ''l''-cysteine. Other isomers include ''d,d''-cystine and the meso isomer d,l-cystine, neither of which is biologically significant. Occurrence Cystine is common in many foods such as eggs, meat, dairy products, and w ...
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Cysteine
Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometimes the symbol Cyz is used. The deprotonated form can generally be described by the symbol Cym as well. The thiol is susceptible to oxidation to give the disulfide derivative cystine, which serves an important structural role in many proteins. In this case, the symbol Cyx is sometimes used. When used as a food additive, it has the E number E920. Cysteine is encoded by the codons UGU and UGC. The sulfur-containing amino acids cysteine and methionine are more easily oxidized than the other amino acids. Structure Like other amino acids (not as a residue of a protein), cysteine exists as a zwitterion. Cysteine has chirality in the older / notation based on homology to - and -glyceraldehyde. In the newer ''R''/''S'' system of de ...
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Disulfur Dichloride
Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. Some alternative names for this compound are ''sulfur monochloride'' (the name implied by its empirical formula, SCl), ''disulphur dichloride'' (British English Spelling) and ''sulphur monochloride'' (British English Spelling). S2Cl2 has the structure implied by the formula Cl−S−S−Cl, wherein the angle between the Cla−S−S and S−S−Clb planes is 90°. This structure is referred to as ''gauche'', and is akin to that for H2O2. A rare isomer of S2Cl2 is S=SCl2; this isomer forms transiently when S2Cl2 is exposed to UV-radiation (see thiosulfoxides). Synthesis, basic properties, reactions Pure disulfur dichloride is a yellow liquid that "smokes" in moist air due to reaction with water. An idealized (but complicated) equation is: :16 S2Cl2 + 16 H2O → 8 SO2 + 32 HCl + 3 S8 It is produced by partial chlorination of elemental sulfur. The reaction proceeds at usable rates at roo ...
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Biochemistry
Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and metabolism. Over the last decades of the 20th century, biochemistry has become successful at explaining living processes through these three disciplines. Almost all areas of the life sciences are being uncovered and developed through biochemical methodology and research.Voet (2005), p. 3. Biochemistry focuses on understanding the chemical basis which allows biological molecules to give rise to the processes that occur within living cells and between cells, Karp (2009), p. 2. in turn relating greatly to the understanding of tissues and organs, as well as organism structure and function. Miller (2012). p. 62. Biochemistry is closely related to molecular biology, which is the study of the molecular mechanisms of biological phenom ...
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Dihedral Angle
A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the union of a line and two half-planes that have this line as a common edge. In higher dimensions, a dihedral angle represents the angle between two hyperplanes. The planes of a flying machine are said to be at positive dihedral angle when both starboard and port main planes (commonly called wings) are upwardly inclined to the lateral axis. When downwardly inclined they are said to be at a negative dihedral angle. Mathematical background When the two intersecting planes are described in terms of Cartesian coordinates by the two equations : a_1 x + b_1 y + c_1 z + d_1 = 0 :a_2 x + b_2 y + c_2 z + d_2 = 0 the dihedral angle, \varphi between them is given by: :\cos \varphi = \frac and satisfies 0\le \varphi \le \pi/2. Alternatively, if an ...
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Nature Reviews Molecular Cell Biology
Nature, in the broadest sense, is the physical world or universe. "Nature" can refer to the phenomena of the physical world, and also to life in general. The study of nature is a large, if not the only, part of science. Although humans are part of nature, human activity is often understood as a separate category from other natural phenomena. The word ''nature'' is borrowed from the Old French ''nature'' and is derived from the Latin word ''natura'', or "essential qualities, innate disposition", and in ancient times, literally meant "birth". In ancient philosophy, ''natura'' is mostly used as the Latin translation of the Greek word ''physis'' (φύσις), which originally related to the intrinsic characteristics of plants, animals, and other features of the world to develop of their own accord. The concept of nature as a whole, the physical universe, is one of several expansions of the original notion; it began with certain core applications of the word φύσις by pre-Socr ...
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