University of Massachusetts Lowell. 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! Lab8_PhenylsuccinicAcid_handout_F20.pdf - OPTICAL Together, these three ions form a salt. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- : 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. The recovered solid is the less-soluble diastereomeric salt of the pair that you made. [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. Nonsuperposable mirror image molecules are called enantiomers. OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID, (From R. Stephani and V. Cesare, Journal of Chemical Education, 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. As the anion binds the H+, it loses its negative charge and becomes poorly soluble in water. Think of a chinal center as an atom to which four different groups are covalently attached. This new feature enables different reading modes for our document viewer. 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. [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. 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. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. [8][29] During ischemia, succinate accumulates. 20, 2372 (2002). So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. Sorry, it seems JavaScript is not enabled in your browser. After refluxing, cool flask for 15 minutes, Chem. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. 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. Molecular Weight: 194.18. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. B. R. Khandavilli, et al., Cryst. [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. Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent Give the % of each enantiomer. [22]:Section 17.4, Succinate is the re-entry point for the gamma-aminobutyric acid (GABA) shunt into the TCA cycle, a closed cycle which synthesizes and recycles GABA. 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. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. The Index number for each substance is in the form of a digit sequence of the type ABC-RST-VW-Y. Melting point-solubility-structure correlations in chiral and racemic Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 with another chiral molecule. At the end of 30 minutes, turn off and remove the heating mantle. [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). Abstract A new co-crystal compound of 4,4'-bipyridine and phenylsuccinic acid was synthesized and characterized by elemental analysis, infrared and ultraviolet-visible spectroscopy, and X-ray single crystal diffraction. The site owner may have set restrictions that prevent you from accessing the site. The proline, its former partner in the salt, remains soluble in the aqueous phase. Home; About us; Membership & professional community . Cloudflare has detected an error with your request. 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! This process In this case, the salt that contains the dextrorotatory acid ("") is the less soluble one, and precipitates. This is a preview of subscription content, access via your institution. The phenylsuccinic acid As a consequence, the mixture cases no net rotation, and appears optically inactive. Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. Experiment 6- Polarimetry and Racemic Mixture - Quizlet Material Safety Data Sheet - Fisher Sci 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. Note that the two diastercomeric salts (S.S) and (R.S) differ in their mions (phenylsuccinate), which are nonsuper-posable mirror images, but have identical cations (L-proline). Thus, via enzymatic inhibition, increased succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation. Curr. [30], Succinate signaling often occurs in response to hypoxic conditions. This application requires Javascript. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. Oversuccination occurs when more than one succinate adds to a substrate. RET at mitochondrial respiratory complex 1, the complex normally preceding SDH in the electron transport chain, leads to ROS production and creates a pro-oxidant microenvironment.[29]. The toxicological properties of this material have In order to recrystallize the solid, boiling water was added to the solid until it fully dissolves to achieve a complete homoge-nous mixture. [30] This leads to stellate cell activation and fibrogenesis. [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. Pure samples of mirror image molecules. After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. This is an ordinary acid-base reaction that produces a salt. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid Water tums [26] As such, succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. Succinic acid (/sksnk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. not been fully investigated. frothy D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Kobra Moradifard, Derikvand, Z. Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! If you study models of chiral molecules, it soon becomes apparent that their mirror images are not superposable on each other. For Research Use Only. 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. This shows the degree to which a sample contains one enantiomer in greater amounts than the other. Orgo exam notes - Exam noted for organic chemistry. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. tory IB Syllabus. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. The phenylsuccinic acid is a proton donor making proline the proton acceptor. 254, 41 (2005). (S)-(&)-Phenylsuccinic acid | CAS 4036-30-0 - SCBT This website collects cookies to deliver a better user experience. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. is conducted between the pheny- [6] It is marketed as food additive E363. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. Succinate thus serves as a direct electron donor to the electron transport chain, and itself is converted into fumarate. PDF Material Safety Data Sheet - Cole-Parmer ACP - Reconsideration of surface tension and phase state effects on For this reason, if the biologically produced. Experiment 4: Resolution of Phenylsuccinic Acid [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. When the solution is cooled down at room temperature, the solubility decreases which allows the pure crystals of phenylsuccinic acid to form. Optically active reagents have long been important, in studies of reaction mechanisms because they may offer glimpses at the molecular details of the process, How does one obtain optically active compounds? M. R. Caira, Mol. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. 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. As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. 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. G. M. Sheldrick, Acta Crystallogr. [8] ROS then trigger the cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc. Write a review Ask a question. The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds. [18], Acylation with succinic acid is called succination. Crystallographic data for the compound was collected at 150(2) K. The synthesized compound is crystallized in the monoclinic system with the space group P21/n and unit cell . 4, 417 (2007). astereomer, enantiomers are iden- [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. In order to recrystallize the. [6] The intermediate is made available for biosynthetic processes through multiple pathways, including the reductive branch of the TCA cycle or the glyoxylate cycle, which are able to drive net production of succinate. The solid was recrystallized and the final solid is filtered out. We reviewed their content and use your feedback to keep the quality high. How does one obtain optically active compounds? 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). Article May cause eye, skin, and respiratory phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- [41], Succinate accumulation under hypoxic conditions has been implicated in the reperfusion injury through increased ROS production. This process produced two diastereomers where the more soluble compound was removed by the HCl. With the product collected, specific rotation was calculated where polarimetry is used to calculate the alpha observed in degrees. stacking interaction leads to the formation of 3D supramolecular structure. [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. 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. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. L8: Optical Resolution: Phenylsuccinic acid Flashcards | Quizlet T. Friscic, L. Fabian, J. C. Burley, et al., Chem. SAFETY DATA SHEET - Fisher Sci 9, 1436 (2009). Specific rotation is defined as [.." - r/le where "-the specific rotation (at 200C using the "D line" of a sodium lamp: units arc (deg x ml. [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. Solved Suppose you want to purify (+)-phenylsuccinic acid - Chegg 7, 4 (2007). This website collects cookies to deliver a better user experience. May cause irritation of the digestive tract. In 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. 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]. Allow to fully dry & poor the filtrate into the aqueous hazardous waste container. Inhibition of KDMs and TET hydroxylases results in epigenetic dysregulation and hypermethylation affecting genes involved in cell differentiation. tract irritation. https://doi.org/10.1134/S1063774519070125, DOI: https://doi.org/10.1134/S1063774519070125. phenylsuccinic salt ()-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. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . Course Hero is not sponsored or endorsed by any college or university. % Molecular Formula: C 10 H 10 O 4. Since our excess is very low, our substance was nowhere near being pure. [40] In spite of a general downregulation of the TCA cycle under these conditions, succinate concentration is increased. (R)-(-)-Phenylsuccinic acid | C10H10O4 | CID 736145 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Scratch inside this test tube several minutes until the contents begin to get cloudy. Molecular Weight: 194.18. Vacuum filter and wash the solid with two 15mL [7] The mechanism by which succinate accumulates in immune cells is not fully understood. 24, 861 (1995). 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). Most often, these pieces can attach to the enzyme only in one particular orientation. Mass of product dissolved in acetone: 0 in short, most biologically. 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. 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. Moreover, the cold water wash and filtration performed was able to recover the crude solid. Colby VPN to 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). (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. 2. add (-) proline, then heat the mixture at reflux for 30 minutes then allow . [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. C. C. Seaton, CrystEngComm 13, 6583 (2011). [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. Enantioseparation of Phenylsuccinic Acid Enantiomers Using Aqueous Two 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--cyclodextrin (HP--CD) in the aqueous phase. Chem. The recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. Lexxus Pen Add 1 of finely ground (s)-proline & a magnetic stir bar then The enantiomeric excess was 35.5% which is the measurement of purity. 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. Brief Profile - ECHA - Europa 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. indication of why you can't access this Colby College website. Phenylsuccinic acid | C10H10O4 | ChemSpider The chiral recognition abilities of . Resulting in observing another groups data: You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. www.colby.edu/directory-profile-update-form you must use the Please enable it to get the best site experience. 4, 310 (2007). Pull air through the solid for a couple of minutes after the last wash to evaporate most of the acetone. 48, 5009 (2006). Shop DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals at Fishersci.com phenylsuccinic acid (H 2A) as the model enantiomers. May cause eye irritation. Multiple studies have demonstrated succinate-induced aggregation, but the effect has high inter-individual variability. PDF Experiment #2 Chemical Resolution of ()-phenylsuccinic Acid With Not Intended for Diagnostic or Therapeutic Use. Expert Answer. Correspondence to Thus, succinate is thought to play a role in liver homeostasis. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function.