Sulfinic acid
... well-studied sulfinic acid is phenylsulfinic acid. A commercially important sulfinic acid is thiourea dioxide, which is ... NH2)2CS + 2H2O2 → (NH)(NH2)CSO2H + 2H2O Another commercially important sulfinic acid is hydroxymethyl sulfinic acid, which is ... One product of this catabolic reaction is the sulfinic acid hypotaurine. Sulfinite also describes esters of sulfinic acid. ... Unsubstituted sulfinic acid, when R is the hydrogen atom, is a higher energy isomer of sulfoxylic acid, both of which are ...
Cysteine sulfinic acid
Peptides containing the cysteine sulfinic acid residue are substrates for cysteine sulfinic acid reductase. Cysteine sulfinic ... It is not a coded amino acid, but is produced post-translationally. It is distinct from cysteine sulfinic acid, H(O)SCH2CH(NH2) ... or enters the cysteine sulfinic acid pathway where it is oxidized by cysteine dioxygenase to form cysteine sulfinic acid. ... It is a rare example of an amino acid bearing a sulfinic acid functional group. It is a white solid that is soluble in water. ...
Phenylsulfinic acid
The preparation of sulfinic acids by the oxidation of thiols is difficult due to overoxidation. In sulfinic acids, sulfur has ... They are prone to oxidation to sulphonic acids as well as reduction via sulphenic acids (+2) to thiols. Sulphinic acid ... This makes phenylsulfinic acid a stronger acid than its corresponding carboxylic acid, benzoic acid (pKa = 4.2), but weaker ... doi:10.1016/S0040-4020(01)83080-5. S. Patai (1990). The Chemistry of Sulphinic Acids, Esters and Their Derivatives. New York: J ...
Sultine
"Cyclic Sulphinic Acid Derivatives (Sultines and Sulphinamides)". In Saul Patai (ed.). Sulphinic Acids, Esters and Derivatives. ... In chemistry, a sultine is a cyclic ester of a sulfinic acid. This class of organosulfur compounds has few applications. These ... compounds are typically prepared by the dehydration of hydroxy-sulfinic acids or their equivalent. Illustrative of an ...
Sulfinamide
... s are amides of sulfinic acid (RS(O)OH). Sulfinamides do not undergo inversion. They can therefore be synthesised ... Sulphinic Acids, Esters and Derivatives. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470772270. ...
Organoselenium chemistry
Seleninic acids (RSe(O)OH) are analogues of sulfinic acids. Selenonic acids (RSe(O)2OH) are analogues of sulfonic acids. ... Selenenic acid (RSe−OH) are intermediates in the oxidation of selenols. They occur in some selenoenzymes, such as glutathione ... This amino acid is encoded in a special manner by DNA. Selenosulfides are also proposed as biochemical intermediates. ... Peroxyseleninic acids (RSe(O)OOH) catalyse epoxidation reactions and Baeyer-Villiger oxidations. Selenuranes are hypervalent ...
Hypochlorous acid
The first reaction yields sulfenic acid (R-SOH) then sulfinic acid (R-SO2H) and finally R-SO3H. Sulfenic acids form disulfides ... Sulfinic acid and R-SO3H derivatives are produced only at high molar excesses of HClO, and disulfides are formed primarily at ... Disulfide bonds can also be oxidized by HClO to sulfinic acid. Because the oxidation of sulfhydryls and disulfides evolves ... Hypochlorous acid (HClO, HOCl, or ClHO) is a weak acid that forms when chlorine dissolves in water, and itself partially ...
Hydroxylamine-O-sulfonic acid
S.L. Graham; T.H. Scholz (1986). "The reaction of sulfinic acid salts with hydroxylamine-O-sulfonic acid. A useful synthesis of ... The reaction of hydroxylamine-O-sulfonic acid with metal salts of sulfinic acids in sodium acetate solution produces primary ... Analogous to sulfamic acid (H3N+SO3−) and as is the case generally for amino acids, HOSA exists in the solid state as a ... The oxime-O-sulfonic acids of aldehydes react above room temperature upon elimination of sulfuric acid in high yields to ...
Angeli-Rimini reaction
After intramolecular proton exchange to 5 a sulfinic acid anion is split off and hydroxamic acid 8 results through nitrone 6 ... The other reaction product is a sulfinic acid. The reaction was discovered by the two Italian chemists Angelo Angeli and Enrico ... A New Approach to Hydroxamic Acids Andrea Porcheddu and Giampaolo Giacomelli J. Org. Chem.; 2006; 71(18) pp 7057 - 7059; (Note ... reaction between an aldehyde and the sulfonamide N-hydroxybenzenesulfonamide in presence of base forming a hydroxamic acid. ...
Ferric chloride test
... hydroxamic acids, oximes, and sulfinic acids give positive results as well. The bromine test is useful to confirm the result, ...
Sulfiredoxin
Woo HA, Jeong W, Chang TS, Park KJ, Park SJ, Yang JS, Rhee SG (2005). "Reduction of cysteine sulfinic acid by sulfiredoxin is ... This view changed with the discovery of sulfiredoxin, an enzyme that can reduce sulfinic acid back to thiol, in an ATP- ... Biteau B, Labarre J, Toledano MB (2003). "ATP-dependent reduction of cysteine-sulphinic acid by S. cerevisiae sulphiredoxin". ... such as sulfinic acid (Cys-SOOH), were once considered irreversible, biologically speaking. ...
Thiourea dioxide
... a sulfinic acid, (H2N)HN=CS(O)(OH), named formamidine sulfinic acid. Thiourea dioxide was first prepared in 1910 by the English ... D. Schubart "Sulfinic Acids and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi: ... US patent 2783272, James H. Young, "PRODUCTION OF FORMAMIDINE SULFINIC ACID", issued 1957-2-26 Rábai, G.; Wang, R. T.; Kustin, ... Sulfinic acids, Thioureas, Amidines, Reducing agents, Substances discovered in the 1910s). ...
Sulfinyl halide
If the nucleophile is water the product is a sulfinic acid, if it is an alcohol the product is a sulfinic ester, if it is a ... Sulfinic acid chlorides, or sulfinyl chlorides, are sulfinyl halides with the general formula R−S(O)−Cl. Methanesulfinyl ... a trifluoroperacetic acid oxidation affords the desired product, as in the case of 2,2,2-trifluoro-1,1-diphenylethanethiol: ...
Desulfonylation reactions
Protonation of the organotin intermediates thus formed (by sulfinic acid generated in situ) leads to reduced products. Addition ... Carboxylic acid derivatives, acetals, thioacetals, amines, alcohols, and isolated double bonds are all inert to Al/Hg. ... Total synthesis of (±)-subergorgic acid". Tetrahedron Letters. 31 (38): 5429. doi:10.1016/S0040-4039(00)97864-X. Vedejs, E.; ... Shindo, Mitsuru; Sugioka, Tomoyuki; Umaba, Yuko; Shishido, Kozo (2004). "Total synthesis of (+)-bongkrekic acid". Tetrahedron ...
Hypotaurine
In the cysteine sulfinic acid pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine ... Kalir, Asher; Kalir, Henry H. "Biological activity of sulfinic acid derivatives" in Chemistry of Sulphinic Acids, Esters Their ... Hypotaurine is a sulfinic acid that is an intermediate in the biosynthesis of taurine. Like taurine, it also acts as an ... Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine. Hypotaurine is ...
SRXN1
2005). "Reduction of cysteine sulfinic acid by sulfiredoxin is specific to 2-cys peroxiredoxins". J. Biol. Chem. 280 (5): 3125- ... 2006). "Molecular mechanism of the reduction of cysteine sulfinic acid of peroxiredoxin to cysteine by mammalian sulfiredoxin ... 2006). "The LIFEdb database in 2006". Nucleic Acids Res. 34 (Database issue): D415-8. doi:10.1093/nar/gkj139. PMC 1347501. PMID ... of mammalian sulfiredoxin and its reactivation of hyperoxidized peroxiredoxin through reduction of cysteine sulfinic acid in ...
GADL1
... has 61% homology with another PLP-dependent enzyme cysteine sulfinic acid decarboxylase (CSAD). CSAD plays a role in ... to β-alanine and cysteine sulfinic acid (CSA) to hypotaurine. GADL1 is a Pyridoxal 5'-phosphate (PLP)-dependent enzyme. By ... "Structure and substrate specificity determinants of the taurine biosynthetic enzyme cysteine sulphinic acid decarboxylase". ... Raasakka A, Mahootchi E, Winge I, Luan W, Kursula P, Haavik J (January 2018). "Structure of the mouse acidic amino acid ...
Sulfonamide
The related sulfinamides (R(S=O)NHR) are amides of sulfinic acids (R(S=O)OH) (see sulfinyl). Chiral sulfinamides such as tert- ... Any sulfonamide can be considered as derived from a sulfonic acid by replacing a hydroxyl group (−OH) with an amine group. In ... Sulfonamide (medicine) Sulfamic acid Sulfamide Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. "Chemotherapeutics". ... Treskow, M.; Neudörfl, J.; Giernoth, R. (2009). "BINBAM - A New Motif for Strong and Chiral Brønsted Acids". Eur. J. Org. Chem ...
Thionyl chloride
... will transform sulfinic acids into sulfinyl chlorides Sulfonic acids react with thionyl chloride to produce ... sulfuric acid, phosphoric acid, chromic acid, etc.]. Comptes rendus (in French). 28: 86-88. Persoz; Bloch (1849). "Addition à ... It adds to alkenes in the presence of AlCl3 to form an aluminium complex which can be hydrolysed to form a sulfinic acid. Both ... sulfuric acid, and sulfurous acid]. Comptes rendus (in French). 28: 389. Kremers, P. (1849). "Ueber schwefligsaures ...
Cysteine dioxygenase
Cysteine sulfinic acid is then metabolized further via two divergent pathways: decarboxylated to hypotaurine by sulfinoalanine ... Cysteine dioxygenase (CDO) is a non-heme iron enzyme that catalyzes the conversion of L-cysteine to cysteine sulfinic acid ( ... It oxidizes cysteine to the corresponding sulfinic acid by activation of dioxygen, although the exact mechanism of the reaction ... CDO oxidizes to cysteine sulfinic acid (which exists predominantly in the anionic sulfinate form in vivo). Overall, CDO ...
Water chlorination
... and sodium hydroxymethane sulfinic acid. Alternative methods for water disinfection Drinking water Safe Drinking Water Act ... Chlorine and the hydrolysis product hypochlorous acid are not charged and therefore easily penetrate the negatively charged ... When dissolved in water, chlorine converts to an equilibrium mixture of chlorine, hypochlorous acid (HOCl), and hydrochloric ... and haloacetic acids (HAAs). Trihalomethanes are the main disinfectant by-products created from chlorination with two different ...
Aurothioglucose
Under physiological conditions, an oxidation-reduction reaction leads to the formation of metallic gold and sulfinic acid ... sulfinic acid derivative of thioglucose) Gold thioglucose can be prepared by treating gold bromide with thioglucose solution ... Naruta E, Buko V (2001). "Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by ...
Thiosulfinate
Takata, T; Endo, T (1990). "Thiosulphinic acids and esters". The Chemistry of Sulphinic Acids, Esters and Their Derivatives, S ... Methyl methanethiosulfinate decomposes thermally giving methanesulfenic acid (CH3SOH), the simplest sulfenic acid, as well as ... Asparagusic acid S-oxide and brugierol are other natural 1,2-dithiolane-1-oxides occurring in Asparagus officinalis and ... tert-Butanethiosulfoxylic Acid". J. Am. Chem. Soc. 94 (2): 644-645. doi:10.1021/ja00757a060. Moore, TL; O'Connor, DE (1966). " ...
Peroxiredoxin 1
Peroxiredoxin
These ensymes are inactivated by over-oxidation (also known as hyperoxidation) of the active thiol to the sulfinic acid (RSO2H ... which undergoes oxidization to a sulfenic acid by the peroxide substrate. The recycling of the sulfenic acid back to a thiol is ... whereas the 1-Cys enzymes may be reduced by ascorbic acid or glutathione in the presence of GST-π. Using high resolution ... Nucleic Acids Research. 39 (Database issue): D332-337. doi:10.1093/nar/gkq1060. ISSN 1362-4962. PMC 3013668. PMID 21036863. ...
Sulfenic acid
In contrast to sulfinic and sulfonic acids, simple sulfenic acids, such as methanesulfenic acid, CH3SOH, are highly reactive ... It is the first member of the family of organosulfur oxoacids, which also include sulfinic acids (R−S(=O)2H) and sulfonic acids ... The sulfenic acid then converts to a disulfide by reaction with another residue of cysteine. Sulfenic acids are produced by the ... In the gas phase the lifetime of methanesulfenic acid is about one minute. The gas phase structure of methanesulfenic acid was ...
Respiratory burst
Sulfhydryl groups can be oxidised up to three times by three HClO molecules, forming sulfenic acids, sulfinic acids and R-SO3H ... The reaction of aqueous hypochlorous acid with alpha-amino acids and dipeptides". Biochimica et Biophysica Acta. 313 (1): 170- ... Hypochlorous acid reacts with a range of biomolecules, including DNA, lipids and proteins. HClO may oxidise cysteines and ... Integral to hypochlorous acid formation is myeloperoxidase. Myeloperoxidase is most abundant in neutrophils, wherein ...
Taurine
... cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase. Cysteine sulfinic acid, in turn ... Mammalian taurine synthesis occurs in the pancreas via the cysteine sulfinic acid pathway. In this pathway, ... Synthetic taurine is obtained by the ammonolysis of isethionic acid (2-hydroxyethanesulfonic acid), which in turn is obtained ... and cysteine sulfinic acid decarboxylase. Hypotaurine is then oxidized to taurine as described above. Taurine occurs naturally ...
Electrophilic amination
... instead of fragmenting into an azide and sulfinic acid, the intermediate triazene salt may break down to a diazo compound and ... although they also may be converted to azides upon acidic workup with overall elimination of sulfinic acid. The most ... trifluoroacetic acid promotes diazo transfer while acetic acid encourages azidation (the reasons for this are unclear). Solvent ... A general approach to the asymmetric synthesis of α-amino acids". J. Am. Chem. Soc. 109 (22): 6881-3. doi:10.1021/ja00256a069. ...
Human serum albumin
... however at high concentrations of reactive species leads to the irreversible oxidation to sulfinic (HSA-SO2H) or sulfonic acid ... ones that are fat-soluble Transports fatty acids ("free" fatty acids) to the liver and to myocytes for utilization of energy ... Komatsu T, Nakagawa A, Curry S, Tsuchida E, Murata K, Nakamura N, Ohno H (September 2009). "The role of an amino acid triad at ... Turell L, Carballal S, Botti H, Radi R, Alvarez B (April 2009). "Oxidation of the albumin thiol to sulfenic acid and its ...
Rongalite
"Sulfinic Acids and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/ ...
Nitrile hydratase
NHases are composed of two types of subunits, α and β, which are not related in amino acid sequence. NHases exist as αβ dimers ... The two Cys residues coordinated to the metal are post-translationally modified to Cys-sulfinic (Cys-SO2H) and -sulfenic (Cys- ... The presence of the amino acid sequence VCTLC indicates a Co-centred NHase and the presence of VCSLC indicates Fe-centred NHase ... Salette, M; Wu R, Sanishvili R, Liu D, Holz RC (2014). "The Active Site Sulfenic Acid Ligand in Nitrile Hydratases can Function ...
Flavin-containing monooxygenase 3
... bacterial FMO is the same as the mammalian FMO activation of thiobenzamide to produce hepatotoxic sulfinic and sulfinic acid ... and could be induced by dietary bile acids through a mechanism that involves FXR (54). Bennett BJ, de Aguiar Vallim TQ, Wang Z ... and the 6-methylhydroxylation of the anti-cancer agent dimethylxanthenone acetic acid (DMXAA). FMO3 is the primary enzyme in ... 6-dimethylxanthenone-4-acetic acid (DMXAA) by flavin-containing monooxygenase 3". Eur J Drug Metab Pharmacokinet. 27 (3): 179- ...
Organic azide
... a diazonium salt reacts with a sulfonamide first to a diazoaminosulfinate and then on hydrolysis the azide and a sulfinic acid ... "A facile cleavage of oxirane with hydrazoic acid in dmf A new route to chiral β-hydroxy-α-amino acids". Tetrahedron Letters. 26 ... Aliphatic alcohols give azides via a variant of the Mitsunobu reaction, with the use of hydrazoic acid. Hydrazines may also ... In the 1890s, Theodor Curtius, who had discovered hydrazoic acid (HN3), described the rearrangement of acyl azides to ...
Smiles rearrangement
This reaction is exemplified by the conversion of an aryl sulfone into a sulfinic acid by action of n-butyllithium: This ...
List of MeSH codes (D02)
... sulfenic acids MeSH D02.886.645.585 - sulfinic acids MeSH D02.886.645.600 - sulfonic acids MeSH D02.886.645.600.055 - ... quinic acid MeSH D02.241.511.852 - shikimic acid MeSH D02.241.511.902 - sugar acids MeSH D02.241.511.902.107 - ascorbic acid ... edetic acid MeSH D02.241.081.038.455 - egtazic acid MeSH D02.241.081.038.581 - iodoacetic acid MeSH D02.241.081.038.581.400 - ... hexuronic acids MeSH D02.241.081.844.915.400.500 - iduronic acid MeSH D02.241.081.901.177 - aconitic acid MeSH D02.241.081.901. ...
Sulfinoalanine decarboxylase
... also known as Cysteine sulfinic acid), and two products, hypotaurine and CO2. This enzyme belongs to the family of lyases, ... L-cysteinesulfinic acid decarboxylase, cysteine-sulfinate decarboxylase, CADCase/CSADCase, CSAD, cysteic decarboxylase, ... cysteinesulfinic acid decarboxylase, cysteinesulfinate decarboxylase, sulfoalanine decarboxylase, and 3-sulfino-L-alanine ...
Perfluorosulfonic acids
2022), "3. Perfluoroalkane sulfonic (a) and sulfinic (b) acids", Fact Cards of Major Groups of Per- and Polyfluoroalkyl ... The simplest example of a perfluorosulfonic acid is the trifluoromethanesulfonic acid. Perfluorosulfonic acids with six or more ... Perfluorooctanesulfonic acid, for example, has been used in hard chromium plating. Perfluorooctanesulfonic acid was included in ... Perfluorosulfonic acids are organofluoroanalogues of conventional alkanesulfonic acids, but they are several pKA units stronger ...
Insect-based pet food
This requirement is based on the low enzymatic action of cysteine dioxygenase and cysteine sulphinic acid decarboxylase within ... taurine not an essential amino acid in the dog); NA, not adequate sample for analysis Amino acids measured on a mg/g DM basis ... This study titled Amino acid content of selected plant, algae and insect species: a search for alternative protein sources for ... created a study to identify amino acid composition of different insects, specifically addressing the presence of taurine in ...