Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol. Resolution of (+/-)-phenylsuccinic acid. not been fully investigated. 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. 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. The resulting solid acid can be recovered by filtration. produced substances are optically active. in short, most biologically. Solubility: Not available. [5] The name derives from Latin succinum, meaning amber. tract irritation. [12][13], Succinic acid can be dehydrogenated to fumaric acid or be converted to diesters, such as diethylsuccinate (CH2CO2CH2CH3)2. The toxicological properties To begin, dissolve 1 of racemic phenylsuccinic acid into 50mL of isopropanol in a Soc. is conducted between the pheny- Proline likewise gains 18+, but this gives ita net + charge, making it very soluble in water. [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. As a consequence, the mixture cases no net rotation, and appears optically inactive. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. [32] Overall, the EC50 for succinate-GPR91 is in the 2050 uM range. : 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. mix contents for 2 minutes and reflux for 30 minutes. tory IB Syllabus. Orgo exam notes - Exam noted for organic chemistry. [citation needed], Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in tumorigenesis. acid into separable diastereomers. OHN 6MH hydrolysis) COH HO COM LPHC Soluble in water produced two diastereomers 32% (R) - 67% (S), To comprehend the conver- CAS Number: 635-51-8. Neutral phenylsuccinic The chiral recognition abilities of the two selectors are opposite . 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. Struct. G. M. Sheldrick, Acta Crystallogr. [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. . Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from wa- Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation, of the plane of polarized light). [26] As such, succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses. However, if the acid is combined with an optically active base, such as (-)-proline, the diastereomers which form have different _____ in isopropyl alcohol. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. A strong acid (6 M HCI), added in excess to the salt, is used to protonate the water-soluble anion. Copyright 2007-2023 Santa Cruz Biotechnology Inc. All Rights Reserved. Generated succinate is then available for either energy production or biosynthesis. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. [citation needed], Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2. [19] Succinic acid is used primarily as an acidity regulator[20] in the food and beverage industry. So, for optical activity to be evident, there must be an excess of one enantiomer over its mirror image. [28], The activity of succinate dehydrogenase (SDH), which interconverts succinate into fumarate participates in mitochondrial reactive oxygen species (ROS) production by directing electron flow in the electron transport chain. [30][32], Extracellular succinate regulates cardiomyocyte viability through GPR91 activation; long-term succinate exposure leads to pathological cardiomyocyte hypertrophy. Please enable it to get the best site experience. Who are the experts? Examples include table sugar, honey, monosodium glutamate (MSG), vitamins, paper (if we could measure it! [33] Therapies targeting succinate to reduce cardiovascular risk and hypertension are currently under investigation.[28]. ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op- For a compound to be optimally pure, it would have to reach up to 171. These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. duce salt. [6] As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. The 'Substance identity' section is calculated from substance identification information from all ECHA databases. Dehydration of succinic acid gives succinic anhydride. 15 mL) and swirl for a minute to mix, then boil gently for 30 min (add boiling chip!). Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. [24][27] In rodents, mitochondrial concentrations are approximately ~0.5 mM[6] while plasma concentration are only 220 M. [ 1], Succinate can alternatively be formed by reverse activity of SDH. In order to recrystallize the. 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. Think of a chiral center as an atom to which four different, groups are covalently attached. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Succinic acid (/ s k s n k /) is a dicarboxylic acid with the chemical formula (CH 2) 2 (CO 2 H) 2. GABA is then metabolized by GABA transaminase to succinic semialdehyde. No information found. Oxidative decarboxylation then generates a ferryl intermediate coordinated to succinate, which serves to oxidize the bound primary substrate. Your email subscription to News & Announcements has been received. Give the % of each enantiomer. This shows the degree to which a sample contains one enantiomer in greater amounts than the other. Pharmacol. 5 mL of DI water. L. Fbin, Cryst. phenylsuccinic salt 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 . Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01. astereomer, enantiomers are iden- Google Scholar. [14] Succinate can be used to derive 1,4-butanediol, maleic anhydride, succinimide, 2-pyrrolidinone and tetrahydrofuran. Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, These chemicals are invariably synthesized by catalysts called, enzymes, which are large chiral molecules specially designed to carry out a particular chemical, transformation. ), . % 2003-2023 Chegg Inc. All rights reserved. Give the % of each enantiomer. 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. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. 254, 41 (2005). where the more soluble compound CAS Number: 4036-30-. The site owner may have set restrictions that prevent you from accessing the site. [12] Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. 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. Home; About us; Membership & professional community . (2018). M. R. Caira, Mol. 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. 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-b-cyclodextrin (HP-b-CD) in the aqueous phase. tical while diastereomers are not [18], Acylation with succinic acid is called succination. 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] Transport across the plasma membrane is likely tissue specific. 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). Eye: In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. 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. Add 2-propanol (approx. [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. This application requires Javascript. ABC corresponds to the atomic number of the most characteristic element or the most characteristic organic group in the molecule. Stir for 5 min to allow complete protonation. 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. The solid that results is now-resolved phenylsuccinic acid in its protonated form. Z. Wang, C. B. Wu, et al., CrystEngComm 14, 6221 (2012). 4, 339 (2007). Typi- Chem. [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. Most often, these pieces can attach to the enzyme only in one particular, orientation. 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. 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. It now must be recovered from the salt (the second step). Don't use too much water, as the product is somewhat soluble and will slowly dissolve. D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. stream The solid that results is now-resolved phenylsuccinic acid in its protonated form. behave identically toward physical tests like melting and boiling points and solubility in given solvents. Percent recovery: 00 100 =4% 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). Succinate and fumarate inhibit the TET (ten-eleven translocation) family of 5-methylcytosine DNA modifying enzymes and the JmjC domain-containing histone lysine demethylase (KDM). [6] It is marketed as food additive E363. Measure the specific rotation and determine the enantiomeric excess of the sample. This process produced two diastereomers where the more soluble compound was removed by the HCl. Lab Section 803 9:00am phenylsuccinic acid (H 2A) as the model enantiomers. 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. Commun. Succinic acid is a white, odorless solid with a highly acidic taste. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. X. P. Dai, G. G. Hou, J. F. Sun, et al., J. Mol. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. This involves an acid-base reaction with (s)-proline and restor- * Refer to Certificate of Analysis for lot specific data (including water content). Molecular Weight: 194.18. 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. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 This diethyl ester is a substrate in the Stobbe condensation. [35] Succinate may interfere with the enzymatic process by attaching to the Fe(II) center first, prohibiting the binding of 2-oxoglutarate. 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. [30], Succinate signaling often occurs in response to hypoxic conditions. o Likely reflux conflict of earlier step in result of failure to eliminate (R)-acid and The information below may provide an The reaction between the bis salt of proline and phenylsuccinic acid will give free phenyl succinic acid and proline hydrochloride as HCl is a much stronger acid than phenylsuccinic acid.
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