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Succinic acid (/sksnk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. Think of a chiral center as an atom to which four different, groups are covalently attached. 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]. [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . Filtration permits discard of the more soluble salt, which cames away one enantiomer () of the phenylsuccinic acid Once the less soluble diastereomeric salt has been isolated, only a single enantiomer of phenylsuccinic acid remains. Experts are tested by Chegg as specialists in their subject area. This is an ordinary acid-basc reaction that produces a salt. CHEM: Organic Chemistry Labora- too much present in sample (soluble) Rep. 64, 10381042 (2019). Google Scholar. Add 2-propanol (approx. At the end of 30 minutes, turn off and remove the heating mantle. Some substance identifiers may have been claimed confidential, or may . Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Growth Des. [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. Proline likewise gains 18+, but this gives ita net + charge, making it very soluble in water. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? A new solvent sublation (SS) system for chiral separation is introduced by using phenylsuccinic acid (H2A) as the model enantiomers. This process University of Massachusetts Lowell. . 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 . The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Iran, Kobra Moradifard,Zohreh Derikvand&Azadeh Azadbakht, You can also search for this author in Solubility:Not available. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. [30] Transport across the plasma membrane is likely tissue specific. Experiment 4: Resolution of Phenylsuccinic Acid [5] The name derives from Latin succinum, meaning amber. Jump to main content Jump to site nav. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. 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. May cause eye, skin, and respiratory Remove the beaker from the ice bath and quickly dry off the outside with a paper towel to prevent water from contaminating the crystals. tract irritation. [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. >> D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Show transcribed image text. [6][26][31] Upon exiting the mitochondria, succinate serves as a signal of metabolic state, communicating to neighboring cells how metabolically active the originating cell population is. 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. As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. The toxicological properties Scratch inside this test tube several minutes until the contents begin to get cloudy. The recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. << Crystallogr. Ingestion: To place an order using RMB or to ship to mainland China, please visit www.scbio.cn, Click on image or enlarge button to enlarge. Commun. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. For Research Use Only. [ 1], Succinate can alternatively be formed by reverse activity of SDH. tainer. Commun. Insoluble in water. with another chiral molecule. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. ;DgEvzv {M aK. The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. not been fully investigated. 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. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. 2023 Springer Nature Switzerland AG. The first source was natural products chemicals produced by living organisms. [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate. so they can be created by reacting 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. [29] If mitochondrial respiratory complex III is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. In this experiment, 2-propanol is the suitable solvent that will selectively precipitate most of one diastercomer and leave most of the other diastercomer in the solution. In This process produced two diastereomers where the more soluble compound was removed by the HCl. phenylsuccinic salt A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. The enantiomeric excess was 35.5% which is the measurement of purity. Most often, these pieces can attach to the enzyme only in one particular orientation. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. Experiment 4: Resolution of Phenylsuccini, The purpose of this experiment is to be able to convert enantiomers of phenylsuccini, ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op-, The Methodology of the Social Sciences (Max Weber), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Psychology (David G. Myers; C. Nathan DeWall), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Give Me Liberty! comes insoluble in water. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. product contains one or more chiral centers, it is optically active. L. Fbin, Cryst. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. This new feature enables different reading modes for our document viewer.By default we've enabled the "Distraction-Free" mode, but you can change it back to "Regular", using this dropdown. <> [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- Nonsuperposable mirror image molecules are called enantiomers. Cross), Civilization and its Discontents (Sigmund Freud), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever). 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. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). Caution! Accumulation of either fumarate or succinate reduces the activity of 2-oxoglutarate-dependent dioxygenases, including histone and DNA demethylases, prolyl hydroxylases and collagen prolyl-4-hydroxylases, through competitive inhibition. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. MONOCLONAL MOUSE ANTI-RABBIT/GOAT SECONDARY ANTIBODIES, POLYCLONAL GOAT/RABBIT ANTI-MOUSE SECONDARY ANTIBODIES, ISOTYPE SPECIFIC MOUSE IgG BINDING PROTEINS, PROTEIN A, G-PLUS & L AGAROSE IP REAGENTS, NUCLEOTIDES, PEPTIDES, PROTEINS & AMINO ACIDS, AUTORADIOGRAPHY FILM, TAPE AND PLASTIC WRAP. Sample will be analyzed by polarimetry. Soc. The solubility of the complexes is poor in the top phase, where H 2 A has better solubility than in the bottom phase. Skin: Garcia, Jessica. 9, 1436 (2009). [19] Succinic acid is used primarily as an acidity regulator[20] in the food and beverage industry. Since our excess is very low, our substance was nowhere near being pure. 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. This is simple since neutral phenylsuccinic acid is poorly soluble in water. The toxicological /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) Add 1 of finely ground (s)-proline & a magnetic stir bar then Typi- cally, the less soluble diastere- omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. 4, 417 (2007). stream Diastecomers are not chemically identical, and so they differ in common physical properties. May cause irritation of the digestive tract. [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. Colby VPN to tiomer behind. 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. Chronic: In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. [38] Hydroxylation of two prolyl residues in HIF1 facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. [8][29] During ischemia, succinate accumulates. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Also calculate the samples enantiomeric excess. Lexxus Pen Measure the specific rotation and determine the enantiomeric excess of the sample. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. properties of this substance have not been fully investigated. a mixture of both enantiomers Shop DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals at Fishersci.com 1035, 203 (2013). [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. The chiral recognition abilities of the two selectors are opposite . Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). This specificity of attachment means that the atoms of the product always end up being connected to each other in only one of several possible ways. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. 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. [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. Who are the experts? 32% (R) - 67% (S), To comprehend the conver- Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid One proline has a position available for one extra proton, so the two protons end up on two different prolines. C. C. Seaton, CrystEngComm 13, 6583 (2011). M. J. Zaworotko, Cryst. connect to this server when you are off campus. Commun. 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 electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state. 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). Percent recovery: 00 100 =4% & Azadbakht, A. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis, Characterization, Crystal Structure, and Supramolecular Interactions. [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. Expert Answer. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 - 173.212.249.81. M. Yoshimura, M. Miyake, T. Kawato, et al., Cryst. The solid was recrystallized and the final solid is filtered out. [6][26][38] PHDs hydroxylate proline in parallel to oxidatively decarboxylating 2-oxyglutarate to succinate and CO2. The phenylsuccinic acid is a proton donor making proline the proton acceptor. Determine the mass of purified crystals and prepare a solution to analyze by polarimetry, first measure about 0.4g of your (S)-phenylsuccinic acid and then dissolve in exactly 10mL of HPLC-grade acetone. ), . Typi- If you have any questions After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. 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. Phenylsuccinic acid Molecular Formula CHO Average mass 194.184 Da Monoisotopic mass 194.057907 Da ChemSpider ID 86155 More details: Names Properties Searches Spectra Vendors Articles More Names and Synonyms Database ID (s) Validated by Experts, Validated by Users, Non-Validated, Removed by Users ()-Phenylsuccinic acid 10424-29- [RN] [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. phenylsuccinic acid (H 2A) as the model enantiomers. Typically, the less soluble diastere-. 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). DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. 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To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- 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. 5, 9 (2002). During this time, all the proline should dissolve. indication of why you can't access this Colby College website. By signing up, you indicate that you have read and agree to the terms in our privacy policy. Sorry, it seems JavaScript is not enabled in your browser. 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. CAS Number: 4036-30-. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Correspondence to Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. 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. 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. Cool 10mL of 6 M HCl in an ice bath and add all of the collected salt to this cold HCl. Growth Des. [36] Additionally, succinate-promoted activation of HIF-1 generates a pseudo-hypoxic state that can promote tumorneogensis by transcriptional activation of genes involved in proliferation, metabolism and angiogenesis. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. Call us Toll Free at 1-800-457-3801. N. Shan, F. Toda, and W. Jones, Chem. Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! Thus, via enzymatic inhibition, increased succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation. Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. On this Wikipedia the language links are at the top of the page across from the article title. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. 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. 1112, 1 (2016). Specific Gravity/Density:Not available.