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 less soluble salt may precipitate. CH 105 Exp 1 Aspirin_with IR Spectrum.pdf, The opioid in New Hamsphire (Autosaved).docx, Muscle There are three types of muscle tissues cardiac muscles which are found, 20 Run other transforms on other websites Task 4 SpiderFoot Independent 17, Malicious unauthorized penetration into information systems Fraud Using, Mathematics_of_finance_Solutions_to_revi.pdf, Part D Calculate the bond dissociation energy needed to break all the bonds in a, Lower environmental costs If firms improve the efficiency of their energy usage, The operations manager schedules quarterly reviews of office equipment whether, Analysis of the Human Relations Theory of Management.docx, Stats Medic - AP Stats - Rules for Means and Variances.pdf, Philippi coins with HPAK countermark 103 Burnet et alii 1992 22 287 Touratsoglou, Uniform Trade Secrets Act I trade secret law developed under the common law but, _Antigone, Scenes 3-5_ Integrated Language Skills.docx, First however it explicates the nature of accounting theories determines the. in short, most biologically. The toxicological properties of this material have Think of a chiral center as an atom to which four different, groups are covalently attached. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. For Research Use Only. Moreover, the cold water wash and filtration performed was able to recover the crude In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. Experiment 4: Resolution of Phenylsuccinic Acid [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. 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. Caution! 15, 2493 (2015). To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate. comes insoluble in water. Crystallogr. Let aspirator run for sev- 7, 1291 (2007). [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. [8] ROS then trigger the cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc. In Resolved (S)-acid: 0, Theoretical yield: 1 2 =0 Together, these three ions form a salt. 1112, 1 (2016). [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. The reaction between the bis salt of proline and phenylsuccinic acid will give free phenyl succinic acid and proline hydrochloride as HCl is a much stronger acid than 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. was removed by the HCl. Neutral phenylsuccinic C. B. Aakery and D. J. Salmon, CrystEngComm 7, 439 (2005). bvseo-msg: The resource to the URL or file is currently unavailable.. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. PubMedGoogle Scholar. [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. Rep. 64, 10381042 (2019). [8][29] During ischemia, succinate accumulates. [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. 17, 550 (2017). produced two diastereomers [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Stir the mixture with a glass rod for 5 minutes. Mass of product dissolved in acetone: 0 Not Intended for Diagnostic or Therapeutic Use. By signing up, you indicate that you have read and agree to the terms in our privacy policy. tiomer behind. the proton acceptor. endobj 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. Cover the beaker or the vial with a watch glass, and keep the beaker covered at all times unless you need to access its contents! mix contents for 2 minutes and reflux for 30 minutes. 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. CAS Number: 4036-30-. To get rid of 2-propanol and any unreacted phenylsuccinic acid, wash the crystals with 10 mL of acetone. 4, 417 (2007). It now must be recovered from the salt (the second step). 9, 1436 (2009). Typi- cally, the less soluble diastere- omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. Santa Cruz Biotechnology, and the Santa Cruz Biotechnology, Inc. logo, Santa Cruz Animal Health, San Juan Ranch, Supplement of Champions, the San Juan Ranch logo, UltraCruz, ChemCruz, ImmunoCruz, ExactaCruz, and EZ Touch are registered trademarks of Santa Cruz Biotechnology, Inc. All trademarks are the property of their respective owners. Scratch inside this test tube several minutes until the contents begin to get cloudy. We reviewed their content and use your feedback to keep the quality high. Lett. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. << eral minutes after the second acetone wash. Poor filtrate into the organic hazardous waste con- As a consequence, the mixture cases no net rotation, and appears optically inactive. [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. : an American History (Eric Foner), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. [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. so they can be created by reacting Upon reperfusion, succinate is rapidly oxidized leading to abrupt and extensive production of ROS. These must be removed to get a good optical activity measurement. Give the % of each enantiomer. 7, 880 (2005). Add 1 of finely ground (s)-proline & a magnetic stir bar then This involves an acid-base reaction with (s)-proline and restor- Keep adding hot water until the solid fully dissolves. T. Friscic, L. Fabian, J. C. Burley, et al., Chem. 24, 861 (1995). [30] Transport across the plasma membrane is likely tissue specific. If you have any questions Call us Toll Free at 1-800-457-3801. 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. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. The chiral recognition abilities of the two selectors are opposite . [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. [26] Alternative, succinate can be released into the extracellular milieu and the blood stream where it is recognized by target receptors. 4, 279 (1987). How does one obtain optically active compounds? (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. Appearance: almost white solid. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. One proline has a position available for one extra proton, so the two protons end up on two different prolines. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- 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. The Some substance identifiers may have been claimed confidential, or may . 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. This shows the degree to which a sample contains one enantiomer in greater amounts than the other. [6][26] Extra-mitochondrial succinate alters the epigenetic landscape by inhibiting the family of 2-oxogluterate-dependent dioxygenases. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). Eye: [28], The activity of succinate dehydrogenase (SDH), which interconverts succinate into fumarate participates in mitochondrial reactive oxygen species (ROS) production by directing electron flow in the electron transport chain. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. 4, 339 (2007). Who are the experts? 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. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 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. Resulting in observing another groups data: Chem. www.colby.edu/directory-profile-update-form you must use the Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid The information below may provide an Inhalation: M. Yoshimura, M. Miyake, T. Kawato, et al., Cryst. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. stream Commun. % The impact of chirality is assessed via comparison of structural features and properties of binary cocrystals. C. C. Seaton, CrystEngComm 13, 6583 (2011). 4, 310 (2007). Let the clear solution rest at RT for about 20 min in order to allow for the crystallization of the desired compound. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Japan (1987), 60, 824-827). Cloudiness and then crystals should gradually form.) 2) Pre-Lab Report: EXPERIMENTAL SECTION 1) Synthesis of diastereomeric salts: Weigh racemic phenylsuccinic acid (0,5g, 2.57 mmole) and L-prolinc (0.3 g. 2.61 mmole) into a 100 ml boiling flask, and swirl to dissolve the solid. 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]. [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. Percent recovery: 00 100 =4% A strong acid (6 M HCI), added in excess to the salt, is poorly soluble in water. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. [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. connect to this server when you are off campus. [12] As an excipient in pharmaceutical products, it is also used to control acidity[21] or as a counter ion. The solid that results is now-resolved phenylsuccinic acid in its protonated form. Soluble in acetone, alcohols, and methanol. Pure samples of mirror image molecules. [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. 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. Such mirror images represent different stereoisomers , they are different molecules. Soc. 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. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic acid into separable diastereomers. These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. Pharmacol. Curr. [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). [30] Depending on the cell type, GPR91 can interact with multiple G proteins, including Gs, Gi and Gq, and enabling a multitude of signaling outcomes. Thus, succinate is thought to play a role in liver homeostasis. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. Commun. This process properties of this substance have not been fully investigated. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. The phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and becomes insoluble in water. product contains one or more chiral centers, it is optically active. Once it was cooled, the purified crystals are collected via vacuum filtration and the final product came out to be 0.399g, thus our concentration being 0.0399g. CHEM: Organic Chemistry Labora- This website collects cookies to deliver a better user experience. GABA is then metabolized by GABA transaminase to succinic semialdehyde. Growth Des. [7] The mechanism by which succinate accumulates in immune cells is not fully understood. 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! Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. succinic acid and proline to pro- 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. 2. the phenylsuccinic acid will precipitate and can be filtered out while the proline is very soluble in water HCl can also be added to (-)-phenylsuccinic acid to release it from any salt which may have formed specific rotation = alpha (observed rotation in degrees)/ l (dm)*c (g/ml) optical purity aka = enantiomeric excess Once the water is boiling, add hot water to the 125mL flask with the solid. In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. May cause skin irritation. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) Allow the flask to air-cool about 10 min. The toxicological properties 2003-2023 Chegg Inc. All rights reserved. Specific Gravity/Density:Not available. Repeat a second time with 15 ml of acetone. [16] The automotive and electronics industries heavily rely on BDO to produce connectors, insulators, wheel covers, gearshift knobs and reinforcing beams. When the solution is cooled down at room temperature, the solubility decreases which allows the pure crystals of phenylsuccinic acid to form. Chronic: 2023 Springer Nature Switzerland AG. [23], Click on genes, proteins and metabolites below to link to respective articles. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. Not Intended for Diagnostic or Therapeutic Use. [39] Other inflammatory cytokines produced by activated macrophages such as tumor necrosis factor or interleukin 6 are not directly affected by succinate and HIF1. Ingestion: this experiment, a reflux reaction Most often, these pieces can attach to the enzyme only in one particular orientation. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. [6] It is marketed as food additive E363. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? ), . where the more soluble compound Once the contents of the flask are near room temperature, take it to a sink and run cold water over the outside for one minute while swirling (NO WATER INSIDE! In order to recrystallize the. All you are really doing is exchanging one acid for another so it is hardly an acid/base reaction. Use a Pasteur pipet to drizzle 1-2 mL of ice-cold water over the entire surface of the solid to wash away as much 6 M HCl as possible. A. V. Trask and W. Jones, Top. [6][26][31] Upon exiting the mitochondria, succinate serves as a signal of metabolic state, communicating to neighboring cells how metabolically active the originating cell population is. Molecular Weight: 194.18. F. Toda and H. Miyamoto, Chem. [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. The calculated specific rotation came out to be 60.65, meaning that it was not optimally pure but the fact that it was positive meaning that it was more of an S enan-tiomer than an R which was preferred. Diastecomers are not chemically identical, and so they differ in common physical properties. "R}~Q:~pgg'"l/O:OV~ @zo7g;)K;=d'}z8}7w7?Iuw?w~ik=w= f.y_j6}Y23 > qB-i%mSiGt{ogo&wMuv!v?qB&p4.IR)>~O4v{x?StuS)F;Nf-iLn)&}tfi7|y]6X4o72{d4j>:h_h=^NC{ ? P4%W,w& y${N~`__/ 1CUoOv|q,foCwa ToC)x;2W`tF2 b2~P2hMD>? Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough At the end of 30 minutes, turn off and remove the heating mantle. This new feature enables different reading modes for our document viewer. Lowell, Massachusetts. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . The difference, however, is subtle. Sample will be analyzed by polarimetry. [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. Measure the specific rotation and determine the enantiomeric excess of the sample. 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. [30], Succinate signaling often occurs in response to hypoxic conditions. L. Fbin, Cryst. 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. Google Scholar. Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Iran, Kobra Moradifard,Zohreh Derikvand&Azadeh Azadbakht, You can also search for this author in A key candidate transporter is INDY (I'm not dead yet), a sodium-independent anion exchanger, which moves both dicarboxylate and citrate into the bloodstream. ADS S. Fernandez-Lopez, H. S. Kim, E. C. Choi, et al., Nature 412, 452 (2001). Growth Des. Molecular Formula: C 10 H 10 O 4. Under pathological and physiological conditions, the malate-aspartate shuttle or the purine nucleotide shuttle can increase mitochondrial fumarate, which is then readily converted to succinate. Since our excess is very low, our substance was nowhere near being pure. 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. With the product collected, specific rotation was calculated where polarimetry is used to calculate the alpha observed in degrees. Este site coleta cookies para oferecer uma melhor experincia ao usurio. Zohreh Derikvand. Sorry, it seems JavaScript is not enabled in your browser. Lexxus Pen No information found. 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. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. 5 mL of DI water. vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. In this case, the salt that contains the dextrorotatory acid ("") is the less soluble one, and precipitates. [27] The GABA shunt serves as an alternate route to convert alpha-ketoglutarate into succinate, bypassing the TCA cycle intermediate succinyl-CoA and instead producing the intermediate GABA. [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. 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. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. HIF1 is known to induce transcription of more than 60 genes, including genes involved in vascularization and angiogenesis, energy metabolism, cell survival, and tumor invasion. Stir for 5 min to allow complete protonation. [5], As a radical group it is called a succinyl (/sksnl/) group. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. ter. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. Growth Des. Stir for 5 min to allow complete protonation. [6][23] Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive reverse electron transport (RET). This is a preview of subscription content, access via your institution. Potential Health Effects The solid that results is now-resolved phenylsuccinic acid in its protonated form.