The toxicological properties of this material have N. Shan, F. Toda, and W. Jones, Chem. M. J. Zaworotko, Cryst. Stir for 5 min to allow complete protonation. Such mirror images represent different stereoisomers , they are different molecules. Abstract. (If there is no precipitate, use a Pasteur pipet to remove about I mL to a small test tube. 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. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). Stir the mixture with a glass rod for 5 minutes. 4, 339 (2007). Phenylsuccinic acid vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. In addition to its metabolic roles, succinate serves as an intracellular and extracellular signaling molecule. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic This process produced two diastereomers where the more soluble compound was removed by the HCl. D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. 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. Expert Answer. RECEIVE -15-CRUZ CREDITS. Resolved (S)-acid: 0, Theoretical yield: 1 2 =0 [10] Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. this experiment, a reflux reaction [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). Diastereomers and Optical Resolution - Chemistry LibreTexts [36] Pathologically elevated levels of succinate lead to hypermethylation, epigenetic silencing and changes in neuroendocrine differentiation, potentially driving cancer formation. Let the clear solution rest at RT for about 20 min in order to allow for the crystallization of the desired compound. The solid that results is now-resolved phenylsuccinic acid in its protonated form. The site owner may have set restrictions that prevent you from accessing the site. PDF Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent acid into separable diastereomers. tical rotation using polarimetry. Calculate the exact concentration which will be needed to calculate specific rotation. Chem. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Give the % of each enantiomer. so they can be created by reacting 5 mL of DI water. Vacuum filter and wash the solid with two 15mL 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. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). (2018). All you are really doing is exchanging one acid for another so it is hardly an acid/base reaction. How does one obtain optically active compounds? The Index number for each substance is in the form of a digit sequence of the type ABC-RST-VW-Y. Phenylsuccinic acid | C10H10O4 | ChemSpider [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Enantioselective separation of R,S-phenylsuccinic acid by biphasic Correspondence to Cloudiness and then crystals should gradually form.) To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- 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. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer [30], Extracellular succinate can act as a signaling molecule with hormone-like function, targeting a variety of tissues such as blood cells, adipose tissue, immune cells, the liver, the heart, the retina and primarily the kidney. S. Mittapalli, M. K. C. Mannava, U. 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. The solid was recrystallized and the final solid is filtered out. To begin, dissolve 1.94g of racemic phenylsuccinic acid into 50mL of isopropanol in a 100mL round bottom flask. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Please enable it to get the best site experience. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. Let aspirator run for several minutes after the second acetone wash. Poor filtrate into the organic hazardous waste container. Exact concentration: 0 10 mL=0. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. 4 0 obj 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. Commun. 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. Cloudflare has detected an error with your request. As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. N. J. Babu, L. S. Reddy, and A. Nangia, Mol. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). https://doi.org/10.1134/S1063774519070125. 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 enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone via the intermediate electron carriers FAD and three 2Fe-2S clusters. [8] ROS then trigger the cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc. Solved Resolution of (+/-)-phenylsuccinic acidThis | Chegg.com The solid that results is now-resolved phenylsuccinic acid in its protonated form. Struct. properties of this substance have not been fully investigated. 9, 1436 (2009). Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. In [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. The toxicological CHEM: Organic Chemistry Labora- Diastecomers are not chemically identical, and so they differ in common physical properties. May cause eye irritation. You have the right to unsubscribe at any time by clicking the 'unsubscribe' link in any News & Announcement emails you receive. 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. The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds. Percent recovery: 00 100 =4% [6] It is marketed as food additive E363. 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. T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. [26], Succinate is also a product of the glyoxylate cycle, which converts two two-carbon acetyl units into the four-carbon succinate. Experiment 4: Resolution of Phenylsuccinic Acid These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. Enantiomers are distinguished from cach other by designations like "R" or "S", "D" or "L", or by the direction of the rotation they cause ("+" or "-") Since the presence of optical activity is an indication of a particular configuration of atoms, any change in optical activity that occurs during a chemical reaction offers a way to study the kind of configurational change that accompanies the reaction. [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. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. [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. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. 4, 310 (2007). Since our excess is very low, our substance was nowhere near being pure. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. At the end of 30 minutes, turn off and remove the heating mantle. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. Material Safety Data Sheet - Fisher Sci Type of reaction between (+)-bis salt of (+)-phenylsuccinic acid and Article 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. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. 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). Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, Conditions to Avoid:Incompatible materials, dust generation, excess heat, strong oxidants. The toxicological properties 7, 1291 (2007). [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. Rep. 64, 10381042 (2019). Swirl and pour as fast as possible into a clean Buchner funnel. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. [7], SUCNR1 is one of the highest expressed G protein-coupled receptors on human platelets, present at levels similar to P2Y12, though the role of succinate signaling in platelet aggregation is debated. [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. [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. Commun. The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. Show transcribed image text. Any rotational effect that one enantiomer has on plane-polarized light will be exactly canceled somewhere else in the mixture by its mirror image. 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). 32% (R) - 67% (S), To comprehend the conver- During this time, all the proline should dissolve. 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. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Part of Springer Nature. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis 15, 2493 (2015). Immediately retum the contents to the boiling flask and swirl. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. 2. add (-) proline, then heat the mixture at reflux for 30 minutes then allow . [26] Alternative, succinate can be released into the extracellular milieu and the blood stream where it is recognized by target receptors. behave identically toward physical tests like melting and boiling points and solubility in given solvents. Solubility: Not available. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough For this reason, if the biologically produced. DL-Phenylsuccinic acid, 98+%, Thermo Scientific Chemicals Add a magnetic stir bar and gently mix the contents of the flask until you achieve a tainer. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. Experts are tested by Chegg as specialists in their subject area. The interactive pathway map can be edited at WikiPathways: Learn how and when to remove this template message, JmjC domain-containing histone lysine demethylase, Institute for Occupational Safety and Health, "Product Information Sheet: Succinic Acid", "Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis", "Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS", Ullmann's Encyclopedia of Industrial Chemistry, "NNFCC Renewable Chemicals Factsheet: Succinic Acid", "Succinate production in Escherichia coli", "Industrial Systems Biology of Saccharomyces cerevisiae Enables Novel Succinic Acid Cell Factory", "Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas", "1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020", "Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism", "Succinic acid in the FDA SCOGS Database", "Overview of pharmaceutical excipients used in tablets and capsules", "Differential effects of complex II on mitochondrial ROS production and their relation to cardioprotective pre- and postconditioning", "Improved Succinate Production by Metabolic Engineering", "Intermediates of Metabolism: From Bystanders to Signalling Molecules", "The succinate receptor as a novel therapeutic target for oxidative and metabolic stress-related conditions", "Succinate metabolism: a new therapeutic target for myocardial reperfusion injury", "GPR91: expanding the frontiers of Krebs cycle intermediates", "Insight into SUCNR1 (GPR91) structure and function", "Inhibition of -KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors", "Oncometabolites: linking altered metabolism with cancer", "Inhibition of hypoxia-inducible factor (HIF) hydroxylases by citric acid cycle intermediates: possible links between cell metabolism and stabilization of HIF", "Succinate is a danger signal that induces IL-1 via HIF-1", "Metabolic reprogramming in macrophages and dendritic cells in innate immunity", "Oncometabolites: Unconventional triggers of oncogenic signalling cascades", "Succinate dehydrogenase and fumarate hydratase: linking mitochondrial dysfunction and cancer", Flame Retardant Finishing of Cotton Fleece Fabric: Part IV-Bifunctional Carboxylic Acids, Calculator: Water and solute activities in aqueous succinic acid, ScienceDirect: Succinic Acid - Production of organic acids and enzymes / biocatalysts from food waste, PubChem: Compound Summary for Succinic Acid, https://en.wikipedia.org/w/index.php?title=Succinic_acid&oldid=1135423431, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Short description is different from Wikidata, Articles with unsourced statements from January 2021, Articles lacking reliable references from March 2017, Creative Commons Attribution-ShareAlike License 3.0, This page was last edited on 24 January 2023, at 15:55. Organic Chemistry I Chem. Polarimetry: The success of this experiment is evaluated by computing the apparent specific rotation of the product. Cool 10mL of 6.0 M HCl in an ice bath and add all of the collected salt to this cold HCl. 1 0 obj 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. Course Hero is not sponsored or endorsed by any college or university. 100mL round bottom flask. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? please help with the following two questions:1. For | Chegg.com Add 1 of finely ground (s)-proline & a magnetic stir bar then Not Intended for Diagnostic or Therapeutic Use. the proton acceptor.