Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. This experiment requires balanced chemical equations and theoretical yield calculation. [11], Genetically engineered Escherichia coli and Saccharomyces cerevisiae are proposed for the commercial production via fermentation of glucose. Molecular Weight: 194.18. Next, place crude solid in a 125mL Erlenmeyer flask and boil 100mL of water in a 250mL Erlenmeyer flask. 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. 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. The difference, however, is subtle. For Research Use Only. Mass of product dissolved in acetone: 0 %PDF-1.4 Scratch inside this test tube several minutes until the contents begin to get cloudy. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. 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. [6] It is marketed as food additive E363. If you study models of chiral molecules, it soon becomes apparent that their, mirror images are not superposable on each other. Solved Resolution of (+/-)-phenylsuccinic acidThis | Chegg.com - 173.212.249.81. [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. May cause eye, skin, and respiratory Single crystal structures, thermal analysis, powder X-ray analysis and equilibrium solubility in water and ethanol of the cocrystals were measured. A. V. Trask and W. Jones, Top. Autocrine succinate signaling promotes retinal neovascularization, triggering the activation of angiogenic factors such as endothelial growth factor (VEGF). 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. Caution! ADS These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. Commun. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. The enantiomeric excess (ee) can be calculated with the expression above, where []mixture and []pureenantiomer are the specific rotations of th. Phenylsuccinic acid [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. Swirl and pour as fast as possible into a clean Buchner funnel. not been fully investigated. succinic acid and proline to pro- 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. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. [5] The name derives from Latin succinum, meaning amber. Keep adding hot water until the solid fully dissolves. The recovered diastereomer must be converted back to the original compound from which it was made -- now a single enantiomer. Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! [5], As a radical group it is called a succinyl (/sksnl/) group. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. The phenylsuccinic acid is a proton donor making proline the proton acceptor. Growth Des. Such mirror images represent different stereoisomers , they are different molecules. PDF Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent Add 1.73 g of (-)-proline. For this reason, if the biologically produced product contains one or more chiral centers, it is optically active Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! 5 mL of DI water. These must be removed to get a good optical activity measurement. 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. Curr. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- [7] For dendritic cells, succinate functions as a chemoattractant and increases their antigen-presenting function via receptor stimulated cytokine production. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid DL-Phenylsuccinic acid Revision Date 24-Dec-2021 Notification Requirements Butanedioic acid, phenyl- 635-51-8 Not applicableNot applicableNot applicableNot applicable 16. Dicarboxylic acids are ubiquitous in atmospheric aerosol particles, but their roles as surfactants in cloud condensation nuclei (CCN) activity remain unclear. sion of an enantiomer to a di- F. Toda and H. Miyamoto, Chem. 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. In this study, we investigated CCN activity of inorganic salt (sodium chloride and ammonium sulfate) and dicarboxylic acid (including malonic acid (MA), phenylmalonic acid (PhMA), succinic acid (SA), phenylsuccinic acid (PhSA . Jump to main content Jump to site nav. OHN 6MH hydrolysis) COH HO COM LPHC Soluble in water RST is the consecutive number of the substance in the series ABC. Typi- We reviewed their content and use your feedback to keep the quality high. [42] The other two oncometabolites, fumarate and 2-hydroxyglutarate have similar structures to succinate and function through parallel HIF-inducing oncogenic mechanisms. Rep. 64, 10381042 (2019). Growth Des. Soluble in acetone, alcohols, and methanol. The solubility of the complexes is poor in the top phase, where H 2 A has better solubility than in the bottom phase. Enzymes required for the GABA shunt are expressed in neurons, glial cells, macrophages and pancreatic cells. Add L-proline (1.15 g 0.01 mole). (S)-(&)-Phenylsuccinic acid | CAS 4036-30-0 - SCBT % You'll get a detailed solution from a subject matter expert that helps you learn core concepts. Struct. Write a review Ask a question. Not Intended for Diagnostic or Therapeutic Use. This website collects cookies to deliver a better user experience. 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. The less soluble salt may precipitate. PDF Material Safety Data Sheet - Cole-Parmer The solid that results is now-resolved phenylsuccinic acid in its protonated form. Please enable it to get the best site experience. GABA is then metabolized by GABA transaminase to succinic semialdehyde. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. 100mL round bottom flask. Garcia, Jessica. Struct. Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . 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. Sorry, it seems JavaScript is not enabled in your browser. Succinic acid is a white, odorless solid with a highly acidic taste. 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. 4, 417 (2007). volumes of cold water. 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. 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. 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 . Repeat a second time with 15 ml of acetone. Think of a chiral center as an atom to which four different, groups are covalently attached. 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. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough [8] ROS then trigger the cellular apoptotic machinery or induce oxidative damage to proteins, membranes, organelles etc. During this time, all the proline should dissolve. 4 0 obj Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. CAS Number: 635-51-8. [26] Alternative, succinate can be released into the extracellular milieu and the blood stream where it is recognized by target receptors. Put the entire crude product into a small beaker or glass vial, and add approx. L8: Optical Resolution: Phenylsuccinic acid Flashcards | Quizlet [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- so they can be created by reacting Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Specific Gravity/Density:Not available. connect to this server when you are off campus. 2023 Springer Nature Switzerland AG. Growth Des. Melting point-solubility-structure correlations in chiral and racemic Percent recovery: 00 100 =4% 5.03E-005 mm Hg (25 deg C, Mod-Grain method) Water Solubility Estimate from Log Kow (WSKOW v1.41): Water Solubility at 25 deg C (mg/L): 4.234e+004 log Kow . https://doi.org/10.1134/S1063774519070125. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. [38] Hydroxylation of two prolyl residues in HIF1 facilitates ubiquitin ligation, thus marking it for proteolytic destruction by the ubiquitin/proteasome pathway. with another chiral molecule. The substance identifiers displayed in the InfoCard are the best available substance name, EC number, CAS number and/or the molecular and structural formulas. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. 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. out to be a good recrystallization solvent for this product. 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. Experts are tested by Chegg as specialists in their subject area. Remove the beaker from the ice bath and quickly dry off the outside with a paper towel to prevent water from contaminating the crystals. [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. Show transcribed image text. This is a preview of subscription content, access via your institution. ()-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. This is simple since neutral phenylsuccinic acid is poorly soluble in water. [32] Furthermore, SUCNR1 synergizes with toll-like receptors to increase the production of proinflammatory cytokines such as TNF alpha and interleukin-1beta. this experiment, a reflux reaction Crystallogr. [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 Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- 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 This process is a proton donor making proline [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. This process produced two diastereomers where the more soluble compound was removed by the HCl. They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer Inhalation: S. L. Childs and K. I. Hardcastle, Cryst. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. 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). In this case, the salt that contains the dextrorotatory acid ("") is the less soluble one, and precipitates. M. R. Caira, Mol. Stir for 5 min to allow complete protonation. Purpose: Upon reperfusion, succinate is rapidly oxidized leading to abrupt and extensive production of ROS. Think of a chinal center as an atom to which four different groups are covalently attached. Nonsuperposable mirror image molecules are called enantiomers. 7, 880 (2005). tainer. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. Colby VPN to 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] 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. May cause skin irritation. T. Friscic, L. Fabian, J. C. Burley, et al., Chem. Allow the flask to air-cool about 10 min. [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate.