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. 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. Scratch inside this test tube several minutes until the contents begin to get cloudy. May cause eye, skin, and respiratory It now must be recovered from the salt (the second step). ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. L. Fbin, Cryst. 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. 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. 100mL round bottom flask. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. produced substances are optically active. 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. With the product collected, specific rotation was calculated where polarimetry is used to calculate the alpha observed in degrees. Call us Toll Free at 1-800-457-3801. 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. connect to this server when you are off campus. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. By signing up, you indicate that you have read and agree to the terms in our privacy policy. 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. 8, 4533 (2008). Growth Des. Add 1 of finely ground (s)-proline & a magnetic stir bar then 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). is conducted between the pheny- Cloudflare has detected an error with your request. May cause irritation of the digestive tract. ter. After refluxing, cool flask for 15 minutes, vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. 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. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. The solid was recrystallized and the final solid is filtered out. Soc. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. Resolution of (+/-)-phenylsuccinic acid. the proton acceptor. N. Shan, A. D. Bond, and W. Jones, Cryst. [26] As such, succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses. duce salt. [38] Hydroxylation of two prolyl residues in HIF1 facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. 4, 417 (2007). 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. Given that enantiomers have identical physical properties, how can the mirror-image molecules become separated without the aid of some living thing? [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. properties of this substance have not been fully investigated. 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]. PubMedGoogle Scholar. Most often, these pieces can attach to the enzyme only in one particular orientation. Put the entire crude product into a small beaker or glass vial, and add approx. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. N. Shan, F. Toda, and W. Jones, Chem. This experiment requires balanced chemical equations and theoretical yield calculation. [5] In an aqueous solution, succinic acid readily ionizes to form its conjugate base, succinate (/sksnet/). To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- M. R. Caira, Mol. 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. Santa Cruz Biotechnology, Inc. is a world leader in the development of products for the biomedical research market. 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. tract irritation. Google Scholar. [30] This leads to stellate cell activation and fibrogenesis. Structure, properties, spectra, suppliers and links for: (+)-Phenylsuccinic acid, 4036-30-. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- Cool 10mL of 6.0 M HCl in an ice bath and add all of the collected salt to this cold HCl. 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. [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. Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. This property is a direct consequence of the configuration, or orientation of bonded atoms in space, around the chiral center. tiomer behind. [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. Soc. succinic acid and proline to pro- 17, 550 (2017). 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. 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. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). Allow to fully dry & poor the filtrate into the aqueous hazardous waste container. Insoluble in water. Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). produced two diastereomers Not Intended for Diagnostic or Therapeutic Use. C. C. Seaton, CrystEngComm 13, 6583 (2011). [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. [28], Succinate serves as a modulator of blood pressure by stimulating renin release in macula densa and juxtaglomerular apparatus cells via GPR91. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. 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? Give the % of each enantiomer. tainer. The proline, its former partner in the salt, remains soluble in the aqueous phase. This involves an acid-base reaction with (s)-proline and restor- 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 . [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. Space available to draw mechanisms. This work presents more extensive results of separation of phenylsuccinic acid enantiomers by biphasic recognition chiral extraction (BRCE), which is an important intermediate of N-methyl--phensuximide and antitumor agents (in Fig. * Refer to Certificate of Analysis for lot specific data (including water content). Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. Rep. 64, 10381042 (2019). Polarimetry: The success of this experiment is evaluated by computing the apparent specific rotation of the product. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity where the more soluble compound Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). 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. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. [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. The 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. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. & Azadbakht, A. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis, Characterization, Crystal Structure, and Supramolecular Interactions. Ingestion: 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. [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. Pharm. T. R. Shattock, K. K. Arora, P. Vishweshwar, and M.J.Zaworotko, Cryst. Nonsuperposable mirror image molecules are called enantiomers. [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. The toxicological properties This process produced two diastereomers where the more soluble compound was removed by the HCl. Struct. A strong acid (6 M HCI), added in excess to the salt, is poorly soluble in water. Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, Eng. 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. Jump to main content Jump to site nav. Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. 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. Lexxus Pen too much present in sample (soluble) Pure samples of mirror image molecules. Calculate the exact concentration which will be needed to calculate specific rotation. Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. Its optical activity can be measured to verify that one enantiomer was isolated in excess over the other In this experiment, racemic (R+S)-phenylsuccinic acid is separated (resolved) into optically active enantiomets in a sequence of two steps. Swirl and pour as fast as possible into a clean Buchner funnel. Commun. Growth Des. CAS Number: 635-51-8. <> 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! Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. [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. Specific Gravity/Density:Not available. 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. Crystallogr. 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. Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. Chem. November 19th, 2018 % [34] 2-oxoglutarate-dependent dioxygenases require an iron cofactor to catalyze hydroxylations, desaturations and ring closures. << * Refer to Certificate of Analysis for lot specific data (including water content). Thus, succinate is thought to play a role in liver homeostasis. phenylsuccinic acid (H 2A) as the model enantiomers. Correspondence to Struct. 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. Skin: Nonsuperposable mirror image molecules are called enantiomers. On this Wikipedia the language links are at the top of the page across from the article title. [5] The name derives from Latin succinum, meaning amber. 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. Transamination and subsequent decarboxylation of alpha-ketoglutarate leads to the formation of GABA. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. 1035, 203 (2013). please email the information below to [emailprotected]. Think of a chinal center as an atom to which four different groups are covalently attached. 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. 5, 9 (2002). 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. Keep adding hot water until the solid fully dissolves. A. V. Trask and W. Jones, Top. Both anions are colorless and can be isolated as the salts, e.g., Na(CH2)2(CO2H)(CO2) and Na2(CH2)2(CO2)2. Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a mix contents for 2 minutes and reflux for 30 minutes. product contains one or more chiral centers, it is optically active. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer [24] Additionally, succinic acid produced during the fermentation of sugar provides a combination of saltiness, bitterness and acidity to fermented alcohols. out to be a good recrystallization solvent for this product. May cause respiratory tract irritation. When the solution is completely ho-mogenous, remove the flask from the hot plate and allow to cool. Add L-proline (1.15 g 0.01 mole). Colby VPN to Organic Chemistry I We reviewed their content and use your feedback to keep the quality high. Home; About us; Membership & professional community . Dehydration of succinic acid gives succinic anhydride. First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. This process produced two diastereomers where the more soluble compound was removed by the HCl. Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). [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. . The phenylsuccinic acid gave up two positives, so it is a dianion. [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. . 4, 310 (2007). Lowell, Massachusetts. Experimental Procedure: Course Hero is not sponsored or endorsed by any college or university. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. 7, 880 (2005). RECEIVE -15-CRUZ CREDITS. Molecular Formula: C 10 H 10 O 4. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. S. Fernandez-Lopez, H. S. Kim, E. C. Choi, et al., Nature 412, 452 (2001). https://doi.org/10.1134/S1063774519070125, DOI: https://doi.org/10.1134/S1063774519070125. Potential Health Effects G. M. Sheldrick, Acta Crystallogr. [11], Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose. [30], Succinate signaling often occurs in response to hypoxic conditions.
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