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. (wikipedia.org)
Thioesters hydrolyze to thiols and the carboxylic acid: RC(O)SR' + H2O → RCO2H + RSH The carbonyl center in thioesters is more reactive toward amine nucleophiles to give amides: In a related reaction, but using a soft-metal to capture the thiolate, thioesters are converted into esters. (wikipedia.org)
Thioesters are involved in the synthesis of all esters, including those found in complex lipids. (wikipedia.org)
Thioesters are compounds resulting from the bonding of sulfur with an acyl group with the general formula R-S-CO-R' . They are the product of esterification between a carboxylic acid and a thiol (as opposed to an alcohol in regular esters ). (chemeurope.com)
Thioesters are created when the sulfur atom in alcohols and thiols interacts with acid catalysts to generate esters. (chemviewconsulting.com)
Now, a research team has found a way to produce sulfinate esters through the direct oxidation of thioesters, which are easily accessible and stable. (sciencedaily.com)
In a recent study published in Organic and Biomolecular Chemistry on 11 August 2023, a research team from Japan has come up with a new approach to synthesize sulfinate esters, a subclass of organosulfur compounds, using thioesters. (sciencedaily.com)
Thioesters have essentially the same chemical structure as esters, except that one or two oxygen atoms are replaced by sulfur atoms. (sciencedaily.com)
These advantages motivated the research team to develop an efficient synthesis route for the synthesis of sulfinate esters via direct oxidation of thioesters. (sciencedaily.com)
Methyl and phenyl esters and thioesters of carboxylic acids as surrogate substrates for microassay of proteinase K esterase activity. (cdc.gov)
Highest rates of hydrolysis have been obtained with the O-phenyl esters CH3(CH2)n = 1 - 2-S-(CH2)n = 1 - 2 C(O)-O-phenyl and their thioester analogs in studies where R, X and R have been varied. (cdc.gov)
Thiols2
Acid anhydrides and some lactones also give thioesters upon treatment with thiols in the presence of a base. (wikipedia.org)
[ 8 ] The malodor associated with pitted keratolysis is presumed to be the production of sulfur-compound by-products, such as thiols, sulfides, and thioesters. (medscape.com)
Synthesis of thioesters1
However, traditional methods for the synthesis of thioesters can have drawbacks such as a need for harsh reaction conditions, odorous materials, or stoichiometric oxidants. (chemistryviews.org)
Alkyl thioesters2
Yahui Li, Anhui Agricultural University, Hefei, China, and colleagues have developed a general procedure to synthesize alkyl thioesters via a Cu/Co co-catalyzed carbonylation of alkyl iodides using alkyl thioesters as reagents (pictured below). (chemistryviews.org)
Di-lower alkyl thioesters of diethylene glycol, or DLTDP, are a thioester in which the sulfur atom is connected to two lower alkyl groups. (chemviewconsulting.com)
Compounds2
The palladium-catalyzed coupling of organozinc compounds with thioesters to form ketones. (organic-chemistry.org)
As previously discussed, mesna binds to the urotoxic cyclophosphamide metabolite acrolein, creating stable thioester compounds with no bladder toxicity. (medscape.com)
Organic3
A thioester forms when a sulfhydryl (whose general form is written as an organic group, R, bonded with sulfur and hydrogen, hence R-SH) joins with a carboxylic acid (R'-COOH). (chemeurope.com)
In this review, we have accommodated the recent reports on modern strategies towards thioester synthesis from a plethora of readily available feedstocks, such as alkenes, alkynes, alcohols, phenols or commodity chemicals/synthetic building blocks like organic aldehydes, halides or organoboron reagents under various catalysis domains. (dntb.gov.ua)
A sulfur atom is connected to an oxygen atom by a carbon-sulfur bond in the thioester class of organic molecules. (chemviewconsulting.com)
Acyl3
Brain tissue ATP concentrations, acyl-Coenzyme A thioesters, and mitochondrial content were also measured. (lu.se)
Finally, there was no change in acyl-coenzyme A thioesters between the two groups. (lu.se)
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. (dadamo.com)
Hydrolases1
This superfamilly includes thioester hydrolases (Families 4.C.3 and 9.B.371) and proteases (8.A.51). (tcdb.org)
According to a research survey conducted by ChemView Consulting, in 2022, the Global Thioesters Market was worth US$ 142.1 Mn and is expected to grow at a CAGR of 4.5% over the forecast period. (chemviewconsulting.com)
Thiol3
They are the product of esterification of a carboxylic acid (R−C(=O)−O−H) with a thiol (R'−S−H). In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. (wikipedia.org)
Methods for the synthesis of N-acetylcysteamine thioesters of beta-keto and alpha,beta-unsaturated acids which avoid problems associated with methods requiring the intermediacy of the free acids are described, along with a convenient method for the removal of excess thiol from reaction mixtures using copper sulphate impregnated silica. (dundee.ac.uk)
The hydrogel dissolution relies on a thiol-thioester exchange mechanism. (rsc.org)
Ester2
The chemical reactions and pathways resulting in the formation of a thioester, a compound of general formula RC(=O)SR' in which the linking oxygen in an ester is replaced by a sulfur atom. (planteome.org)
Afterwards, the thioester was directly oxidized in the presence of N -bromosuccinimide, which created an intricate reaction pathway culminating with the formation of a sulfinate ester. (sciencedaily.com)
Reactions2
Thioesters are common intermediates in many biosynthetic reactions, including the formation and degradation of fatty acids and mevalonate, precursor to steroids. (wikipedia.org)
Fluorinated malonic acid half thioesters (F-MAHTs) were used as thioester enolate equivalents in organocatalyzed addition reactions to isatins. (nih.gov)
Molecule1
They first prepared a desired thioester molecule from an aryl iodide composed of an aryl group bound to an iodine atom. (sciencedaily.com)
Surrogates2
Chlorinated malonic acid half thioesters were established as chloroacetate surrogates and used in stereoselective organocatalyzed decarboxylative aldol-type additions. (nih.gov)
Dawson, P. E. Leveraging the Knorr pyrazole synthesis for the facile generation of thioester surrogates for use in native chemical ligation. (scripps.edu)
Reactive1
After activation C3b can bind covalently, via its reactive thioester, to cell surface carbohydrates or immune aggregates. (abcam.com)
Organozinc1
A reaction unique to thioesters is the Fukuyama coupling, in which the thioester is coupled with an organozinc halide by a palladium catalyst to give a ketone. (wikipedia.org)
Sulfur atom1
Oxidation of the sulfur atom in thioesters (thiolactones) is postulated in the bioactivation of the antithrombotic prodrugs ticlopidine, clopidogrel, and prasugrel. (wikipedia.org)
Carbon-sulf1
Using a copper-containing catalyst, the researchers managed to strip the iodine atom from the aryl group and replace it with a carbon-sulfur bond, forming a thioester. (sciencedaily.com)
Biosynthetic2
Link to all annotated objects annotated to thioester biosynthetic process. (planteome.org)
Link to all direct and indirect annotations to thioester biosynthetic process. (planteome.org)
Yields3
In both these instances, the thioester is closer than ATP to the process that uses or yields energy. (wikipedia.org)
The desired thioesters were obtained in moderate to good yields. (chemistryviews.org)
Self-editing of the tag and subsequent trans-thioesterification yields peptide thioesters. (tokushima-u.ac.jp)
Proteins4
In addition, thioesters play an important role in the tagging of proteins with ubiquitin, which tags the protein for degradation. (wikipedia.org)
There is paucity of information on functional relationship and characterization of Biomphalaria glabrata thioester-containing proteins ( Bg TEP) to other well-annotated homologues. (ac.ir)
The predicted role of thioester-containing proteins to be involved in immunological role in B. glabrata may have a strong effect on resistance to infection. (ac.ir)
Functional2
Molecules containing thioester functional groups are important, e.g., in the pharmaceutical and agrochemical fields. (chemistryviews.org)
Two of the functional groups in the thioester DLTDP include sulfur. (chemviewconsulting.com)
Bonds3
Eventually, [these] thioesters could have served to usher in ATP through its ability to support the formation of bonds between phosphate groups. (wikipedia.org)
The thioester bond is what biochemists call a high-energy bond, equivalent to the phosphate bonds in adenosine triphosphate ( ATP ), which is the main supplier of energy in all living organisms. (chemeurope.com)
Thioesters can be conveniently prepared from alcohols by the Mitsunobu reaction, using thioacetic acid. (wikipedia.org)
Acid2
The biosynthesis of lignin, which comprises a large fraction of the Earth's land biomass, proceeds via a thioester derivative of caffeic acid. (wikipedia.org)
Thioester hydrolyses have been monitored continuously with 5,5-dithio-bis (2-nitrobenzoic acid). (cdc.gov)
Explains1
As Christian de Duve explains: It is revealing that thioesters are obligatory intermediates in several key processes in which ATP is either used or regenerated. (wikipedia.org)
Methods1
Transition metal catalysis and radical reaction manifolds have enabled to enrich the repertoire of synthetic methods for thioesters. (dntb.gov.ua)
Addition2
In addition, thioesters are formed as key intermediates in several particularly ancient processes that result in the assembly of ATP. (wikipedia.org)
Oxidative addition of the thioester is followed by transmetalation from the zinc compound. (organic-chemistry.org)
Interestingly, you'll note the thioester as protecting group. (organic-chemistry.org)
Wikipedia1
It uses material from the Wikipedia article "Thioester" . (chemeurope.com)
World3
As posited in a "Thioester World", thioesters are possible precursors to life. (wikipedia.org)
In other words, thioesters could have actually played the role of ATP in a "thioester world" initially devoid of ATP. (wikipedia.org)
One Nobel Prize winning scientist, Belgium's Christian de Duve, posits a "Thioester World," which preceded and developed into an " RNA World ," itself the immediate precursor to the appearance of entities we would call organisms. (chemeurope.com)
Give1
Thioesters are an antioxidant ingredient to give lubricating solutions the qualities above, increasing demand for thioesters across sectors. (chemviewconsulting.com)
Application1
Rubber processing will continue to be a major application area for thioesters globally. (chemviewconsulting.com)