The phenylsuccinic acid acts as the proton donor, while proline is the proton acceptor OH Ph OH OH Ph protoner) acid-base reaction OH SINH phreyhuccinic acid L-prolier (base) equimolarite of R+5) (5) PLUS The two salts shown above are stereoisomers that are not mirror images, so are a pair of diastereomers. Stir for 5 min to allow complete protonation. 4,4-Bipyridine and 1,2-bis(4-pyridyl)ethane were combined with achiral, racemic mixture or pure enantiomers of selected carboxylic acids with similar constituents (p-toluic acid, rac-2-phenylbutyric acid, racemic or S-phenylsuccinic acid). 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. J. M. Chen, Z. 15, 2493 (2015). The name derives from Latin succinum, meaning amber.In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the . Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. Experts are tested by Chegg as specialists in their subject area. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agencys EPISuite, Compounds with the same molecular formula, Search Google for structures with same skeleton, CAUTION: May irritate eyes, skin, and respiratory tract. 48, 5009 (2006). It now must be recovered from the salt (the second step). Vacuum filter and wash the solid with two 15mL volumes of cold water. Oversuccination occurs when more than one succinate adds to a substrate. 1035, 203 (2013). Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. Anyone you share the following link with will be able to read this content: Sorry, a shareable link is not currently available for this article. In this study, we investigated CCN activity of inorganic salt (sodium chloride and ammonium sulfate) and dicarboxylic acid (including malonic acid (MA), phenylmalonic acid (PhMA), succinic acid (SA), phenylsuccinic acid (PhSA . [38] Hydroxylation of two prolyl residues in HIF1 facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . Solubility: Not available. ORGO WEEK 2 PRAC QUIZ - practice for orgo quiz 1 and 2. [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. Solubility:Not available. The difference, however, is subtle Pure samples of mirror image molecules behave identically toward physical tests like melting and boiling points and solubility in given solvents The only way that these isomers differ physically is the direction in which they rotate plane-polarized light -their optical activity. The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. Google Scholar. This diethyl ester is a substrate in the Stobbe condensation. Please enable it to get the best site experience. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. volumes of cold water. For this reason, if the biologically produced. produced substances are optically active. OHN 6MH hydrolysis) COH HO COM LPHC Soluble in water Mass of product dissolved in acetone: 0 Specific rotation is a property of a chiral substance that is expressed as the angle to which the material causes polarized light to rotate, passing through the tube containing solution. The answer lies in converting the mixture of enantiomers into different compounds - a pair of diastereomers (stereoisomers that are not mitror images of each other). The solid that results is now-resolved phenylsuccinic acid in its protonated form. Succinate requires specific transporters to move through both the mitochondrial and plasma membrane. You convert the (+)-phenylsuccinic acid to a salt with proline, separate the 2 diastereomers based on solubility differences, and recover the neutral phenylsuccinic acid through the following steps: 1. mix racemic phenylsuccinic acid with isopropyl alcohol; dissolve. [32] The ligand specificity of GPR91 was rigorously tested using 800 pharmacologically active compounds and 200 carboxylic acid and succinate-like compounds, all of which demonstrated significantly lower binding affinity. A new solvent sublation (SS) system for chiral separation is introduced by using phenylsuccinic acid (H2A) as the model enantiomers. Not Intended for Diagnostic or Therapeutic Use. [41], Succinate accumulation under hypoxic conditions has been implicated in the reperfusion injury through increased ROS production. [30] In the second step of mitochondrial export, succinate readily crosses the outer mitochondrial membrane through porins, nonspecific protein channels that facilitate the diffusion of molecules less than 1.5 kDa. [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. configuration enantiomer, the other diastereomer must be more soluble during the filtration [30] In general, leakage from the mitochondria requires succinate overproduction or underconsumption and occurs due to reduced, reverse or completely absent activity of SDH or alternative changes in metabolic state. In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. The recovered solid is the less-soluble diastereomeric salt of the pair that you made. [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity [11], Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose. Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. M. R. Caira, Mol. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. Struct. PubMedGoogle Scholar. No information found. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. stream Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Generated succinate is then available for either energy production or biosynthesis. phenylsuccinic salt [30] Stimulation of GPR91 triggers at least two signaling pathways in the heart: a MEK1/2 and ERK1/2 pathway that activates hypertrophic gene expression and a phospholipase C pathway which changes the pattern of Ca2+ uptake and distribution and triggers CaM-dependent hypertrophic gene activation. [ 1], Succinate can alternatively be formed by reverse activity of SDH. The Index number for each substance is in the form of a digit sequence of the type ABC-RST-VW-Y. Space available to draw mechanisms. InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14), CSID:86155, http://www.chemspider.com/Chemical-Structure.86155.html (accessed 08:22, Mar 4, 2023), Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agencys EPISuite, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. By signing up, you indicate that you have read and agree to the terms in our privacy policy. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. A. V. Trask and W. Jones, Top. F. Toda and H. Miyamoto, Chem. It was concluded that the aqueous solubility of the cocrystals is inversely related to their melting points and this trend can be linked to some packing features. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. The experiments were carried out in a traditional SS apparatus but with collaborative chiral selectors: dibenzoyl-L-tartaric acid (L-DBTA) in the organic phase and hydroxypropyl-b-cyclodextrin (HP-b-CD) in the aqueous phase. Article [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. Put the entire crude product into a small beaker or glass vial, and add approx. The solubility of the complexes is poor in the top phase, where H 2 A has better solubility than in the bottom phase. Phenylsuccinic acid | C10H10O4 - PubChem Phenylsuccinic acid | C10H10O4 | CID 95459 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome, and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury.[6][7][8]. Potential Health Effects Commun. 4 0 obj In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. [36][37], Succinate inhibition of prolyl hydroxylases (PHDs) stabilizes the transcription factor hypoxia inducible factor (HIF)1. Pharm. was removed by the HCl. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Succinate is generated from succinyl-CoA by the enzyme succinyl-CoA synthetase in a GTP/ATP-producing step:[22]:Section 17.1, Succinyl-CoA + NDP + Pi Succinate + CoA + NTP, Catalyzed by the enzyme succinate dehydrogenase (SDH), succinate is subsequently oxidized to fumarate:[22]:Section 17.1, SDH also participates in the mitochondrial electron transport chain, where it is known as respiratory complex II. The proline, its former partner in the salt, remains soluble in the aqueous phase. 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. Don't use too much water, as the product is somewhat soluble and will slowly dissolve. 4, 310 (2007). Pull air through the solid for a couple of minutes after the last wash to evaporate most of the acetone. [6][22]:Section 17.1 All metabolic pathways that are interlinked with the TCA cycle, including the metabolism of carbohydrates, amino acids, fatty acids, cholesterol, and heme, rely on the temporary formation of succinate. Vacuum filter and wash the solid with two 15mL S. L. Childs and K. I. Hardcastle, Cryst. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. [30] Transport across the plasma membrane is likely tissue specific. This process produced two diastereomers where the more soluble compound was removed by the HCl. [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. In 9, 1436 (2009). Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agencys EPISuite, Compounds with the same molecular formula, Search Google for structures with same skeleton, CAUTION: May irritate eyes, skin, and respiratory tract. Jump to main content Jump to site nav. [12], In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass. [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. [35] First, 2-oxoglutarate coordinates with an Fe(II) ion bound to a conserved 2-histidinyl1-aspartyl/glutamyl triad of residues present in the enzymatic center. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. Lett. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. Swirl and pour as fast as possible into a clean Buchner funnel. The enantiomeric excess was 35.5% which is the measurement of purity. * Refer to Certificate of Analysis for lot specific data (including water content). Your email subscription to News & Announcements has been received. Proceed to measure the specific rotation of the sample and calculate the enantiomeric excess 4) Recrystallization: The recovered acid contains contaminants- possibly some left-over proline and some HCl or some of the enantiomeric succinic acid. product contains one or more chiral centers, it is optically active. Resolution of (+/-)-phenylsuccinic acid. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. Diastecomers are not chemically identical, and so they differ in common physical properties. Moreover, the cold water wash and filtration performed was able to recover the crude solid. ()-phenylsuccinic acid N CO 2H H H (-)-Proline Week 1: Resolution of ()-phenylsuccinic acid Procedure In a clean, dry, 250 mL round-bottomed flask, dissolve 2.9 g of ()-phenylsuccinic acid in 75 mL of 2-propanol. 2. add (-) proline, then heat the mixture at reflux for 30 minutes then allow . Use a Pasteur pipet to drizzle 1-2 mL of ice-cold water over the entire surface of the solid to wash away as much 6 M HCl as possible. (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. A 71, 3 (2015). For Research Use Only. eral minutes after the second acetone wash. Poor filtrate into the organic hazardous waste con- Think of a chiral center as an atom to which four different, groups are covalently attached. Experiment 4: Resolution of Phenylsuccinic Acid OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74, 1226, 1997) 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they are converted into a mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation of one compound from a mixture of compounds. Caution! Commun. Kobra Moradifard, Derikvand, Z. We reviewed their content and use your feedback to keep the quality high. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Dehydration of succinic acid gives succinic anhydride. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. In living organisms, primarily succinate, not succinic acid, is found. Under anaerobic conditions certain bacteria such as A. succinogenes, A. succiniciproducens and M. succiniciproducens, run the TCA cycle in reverse and convert glucose to succinate through the intermediates of oxaloacetate, malate and fumarate. . This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. Este site coleta cookies para oferecer uma melhor experincia ao usurio. phenylsuccinic acid (H 2A) as the model enantiomers. D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Exact concentration: 0 10 mL=0. After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. [citation needed], Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in tumorigenesis. The first source was natural products , chemicals produced by living organisms. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14)/t8-/m0/s1, CSID:643286, http://www.chemspider.com/Chemical-Structure.643286.html (accessed 08:22, Mar 4, 2023), Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agencys EPISuite, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. Typically, the less soluble diastere-. The phenylsuccinic acid is a proton donor making proline the proton acceptor. 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. 5.03E-005 mm Hg (25 deg C, Mod-Grain method) Water Solubility Estimate from Log Kow (WSKOW v1.41): Water Solubility at 25 deg C (mg/L): 4.234e+004 log Kow . Such mirror images represent different stereoisomers , they are different molecules. The first source was natural products chemicals produced by living organisms. Neutral phenylsuccinic OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74.1226, 1997 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they are converted into a mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation of one compound from a mixture of compounds. 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The possibility of why the specific rotation was so low was because the concentration might have been too low to consider in the first place. Polarimetry: The success of this experiment is evaluated by computing the apparent specific rotation of the product. The toxicological Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. For a compound to be optimally pure, it would have to reach up to 171. Together, these three ions form a salt. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. High concentrations of succinate will mimic the hypoxia state by suppressing PHDs,[37] therefore stabilizing HIF1 and inducing the transcription of HIF1-dependent genes even under normal oxygen conditions. Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, 7, 880 (2005). astereomer, enantiomers are iden- 8, 4533 (2008). Specific Gravity/Density:Not available. It washes away in the acidic water, leaving nearly pure phenylsuccinic acid as the solid.) Expert Answer. For this reason, if the biologically produced product contains one or more chiral centers, it is optically active Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), InChI=1/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8), Except where otherwise noted, data are given for materials in their, Precursor to polymers, resins, and solvents. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. The site owner may have set restrictions that prevent you from accessing the site. For Research Use Only. Soluble in acetone, alcohols, and methanol. CAS Number: 635-51-8. Let aspirator run for sev- Molecular Weight: 194.18. ;DgEvzv {M aK. The chiral recognition abilities of the two selectors are opposite . Scratch inside this test tube several minutes until the contents begin to get cloudy. OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74.1226, 1997 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they. Specific Gravity/Density:Not available. Requested URL: www.colby.edu/chemistry/CH241F/Experiment%202.pdf, User-Agent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/103.0.5060.114 Safari/537.36 Edg/103.0.1264.62. Vis x dm) r=the observed angular rotation of planc-polarized light in degrees 1 - cell path length in decimeters (1 dm - 10 cm; use I dm in equation) c-concentration of compound in g'mL of solution The published specific rotation of (+-phenylsuccinic acid is +173.3" (Shiraiwa, T., Sado, Y, Fujii, S. Nakamura, M., Kurokawo, H., Bull. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. tical while diastereomers are not Water tums [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. Add L-proline (1.15 g 0.01 mole). Chem. duce salt. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in https://doi.org/10.1134/S1063774519070125. L. Fbin, Cryst. Growth Des. Succinate is also produced from butane via maleic anhydride. [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Growth Des. Resolved (S)-acid: 0, Theoretical yield: 1 2 =0 4, 417 (2007). Succinate and fumarate inhibit the TET (ten-eleven translocation) family of 5-methylcytosine DNA modifying enzymes and the JmjC domain-containing histone lysine demethylase (KDM). Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. bvseo-msg: The resource to the URL or file is currently unavailable.. 7, 4 (2007). During this time, all the proline should dissolve. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Soc. acid into separable diastereomers. Orgo exam notes - Exam noted for organic chemistry. Insoluble in water. Calculate the exact concentration which will be needed to calculate specific rotation. not been fully investigated. Enantiomeric excess: of (+)-phenylsuccinic acid, To comprehend the conversion of an enantiomer to a di-astereomer, enantiomers are identical while diastereomers are not so they can be created by reacting a mixture of both enantiomers with another chiral molecule. Molecular Formula: C 10 H 10 O 4. 2023 Springer Nature Switzerland AG. <> [6][23] Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive reverse electron transport (RET). 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However, if the acid is combined with an optically active base, such as (-)-proline, the diastereomers which form have different _____ in isopropyl alcohol. where the more soluble compound produced two diastereomers [5], As a radical group it is called a succinyl (/sksnl/) group. [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. ), 2) Recovery of less soluble salt: Vacuum filter the contents of the flask using a medium Buchner funnel.