* Refer to Certificate of Analysis for lot specific data (including water content). CHEM: Organic Chemistry Labora- % Article Chem. Potential Health Effects Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 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. tiomer behind. Vacuum filter and wash the solid with two 15mL volumes of cold water. 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. Give the % of each enantiomer. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. 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. Growth Des. Add 1.73 g of (-)-proline. Commun. The phenylsuccinic acid is a proton donor making proline the proton acceptor. 5 mL of DI water. [12], In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass. Thus, via enzymatic inhibition, increased succinate load can lead to changes in transcription factor activity and genome-wide alterations in histone and DNA methylation. Upon reperfusion, succinate is rapidly oxidized leading to abrupt and extensive production of ROS. 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. too much present in sample (soluble) The acid and base are structurally more complex than HCl and NH3, but the concept is the same. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). 4, 339 (2007). 4, 279 (1987). C. B. Aakery and D. J. Salmon, CrystEngComm 7, 439 (2005). 5, 9 (2002). [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. The phenylsuccinic acid gave up two positives, so it is a dianion. The toxicological properties of this material have 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. One proline has a position available for one extra proton, so the two protons end up on two different prolines. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. Phenylsuccinic acid (H 2 A, racemate, purity 99 %) was purchased from DiBo (Shanghai, China) and polyethyleneglycol (PEG) was provided by Guangzhou (Guangdong, . High concentrations of succinate will mimic the hypoxia state by suppressing PHDs,[37] therefore stabilizing HIF1 and inducing the transcription of HIF1-dependent genes even under normal oxygen conditions. [31] SDH mutations have also been identified in gastrointestinal stromal tumors, renal tumors, thyroid tumors, testicular seminomas and neuroblastomas. [5] The name derives from Latin succinum, meaning amber. Cloudflare has detected an error with your request. Mutations in SDH, hypoxia or energetic misbalance are all linked to an alteration of flux through the TCA cycle and succinate accumulation. This diethyl ester is a substrate in the Stobbe condensation. To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a 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. Alternate Names: Phenylsuccinic acid. These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that, are to be fashioned into the product. November 19th, 2018 [27], Succinate is produced and concentrated in the mitochondria and its primary biological function is that of a metabolic intermediate. 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. Home; About us; Membership & professional community . Part of their specificity lies in how they bind, or attract and hold, the molecular pieces that are to be fashioned into the product. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). J. M. Chen, Z. Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. Together, these three ions form a salt. First, we exploit its chemical nature it is an acid) by treating it with an optically active biologically produced base, L-proline. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. May cause irritation of the digestive tract. Skin: 2023 Springer Nature Switzerland AG. [6][23] Under conditions of succinate accumulation, rapid oxidation of succinate by SDH can drive reverse electron transport (RET). duce salt. [29] If mitochondrial respiratory complex III is unable to accommodate excess electrons supplied by succinate oxidation, it forces electrons to flow backwards along the electron transport chain. The proline, its former partner in the salt, remains soluble in the aqueous phase. astereomer, enantiomers are iden- The solid was recrystallized and the final solid is filtered out. N. Shan, F. Toda, and W. Jones, Chem. Most often, these pieces can attach to the enzyme only in one particular orientation. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- Succinate is also produced from butane via maleic anhydride. 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 . How does one obtain optically active compounds? Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste. Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! produced two diastereomers Once the water is boiling, add hot water to the 125mL flask with the solid. Enantiomeric excess: 60.65171=0 100 =35% of (+)-phenylsuccinic acid [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. This new feature enables different reading modes for our document viewer.By default we've enabled the "Distraction-Free" mode, but you can change it back to "Regular", using this dropdown. [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. [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. sion of an enantiomer to a di- >> 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 . Nonsuperposable mirror image molecules are called enantiomers. Course Hero is not sponsored or endorsed by any college or university. L. Fbin, Cryst. The less soluble salt may precipitate. F. Toda, K. Tanaka, A. Sekikawa, J. Chem. Inhalation: A suitable solvent is found by trial and error. Most often, these pieces can attach to the enzyme only in one particular, orientation. [17] Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. Succinate is generated from succinyl-CoA by the enzyme succinyl-CoA synthetase in a GTP/ATP-producing step:[22]:Section 17.1, Succinyl-CoA + NDP + Pi Succinate + CoA + NTP, Catalyzed by the enzyme succinate dehydrogenase (SDH), succinate is subsequently oxidized to fumarate:[22]:Section 17.1, SDH also participates in the mitochondrial electron transport chain, where it is known as respiratory complex II. [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. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. The solid that results is now-resolved phenylsuccinic acid in its protonated form. Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough Pharm. tainer. Moreover, the cold water wash and filtration performed was able to recover the crude /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) Growth Des. Diastecomers are not chemically identical, and so they differ in common physical properties.