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In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters ( R−C(=O)−O−R’ ) with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix.
In organic chemistry, a sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. [1] A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen.
The biosynthesis and degradation of fatty acids and related long-chain hydrocarbons is conducted on a scaffold that anchors the growing chain through a thioester derived from the thiol Coenzyme A. The biosynthesis of methane, the principal hydrocarbon on Earth, arises from the reaction mediated by coenzyme M, 2-mercaptoethyl sulfonic acid ...
For example, from the word ether, referring to an oxygen-containing compound having the general chemical structure R−O−R′, where R and R′ are organic functional groups and O is an oxygen atom, comes the word thioether, which refers to an analogous compound with the general structure R−S−R′, where S is a sulfur atom covalently ...
Thioesters are prominent active esters, as illustrated by the esters of coenzyme A. [3] In synthetic chemistry, active esters include derivatives of nitrophenols and pentafluorophenol. Active esters are often used in peptide synthesis, e.g., N-hydroxysuccinimide, hydroxybenzotriazole. [1]
To participate in specific metabolic processes, fatty acids must first be activated by being joined in thioester linkage (R-CO-SCoA) to the -SH group of coenzyme A, where R is a fatty carbon chain. The thioester bond is a high energy bond. [1] The activation reaction normally occurs in the endoplasmic reticulum or the outer mitochondrial membrane.
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Alkylation of the corresponding thioate ion gives a thioester. [9] The conjugate base of thioacetic acid, thioacetate, is a reagent used for installing thiol groups via the displacement of alkyl halides by a two-step process. The halide is displaced to give a thioester intermediate, which is then hydrolyzed: R−X + CH 3 COS − → R−SC(O)CH ...