Succinic Acid
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Crystallization of Malonic and Succinic Acids on Sams: Toward the General Mechanism of Oriented Nucleation on Organic Monolayers†
pubs.acs.org/Langmuir © 2009 American Chemical Society Crystallization of Malonic and Succinic Acids on SAMs: Toward the General Mechanism of Oriented Nucleation on Organic Monolayers† Boaz Pokroy,‡ Victoria Fay Chernow, and Joanna Aizenberg* School of Engineering and Applied Sciences, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138. ‡ Current address: Department of Materials Engineering, Israel Institute of Technology, Haifa 32000, Israel. Received July 25, 2009. Revised Manuscript Received September 2, 2009 Self-assembled monolayers (SAMs) were shown to induce very specific oriented growth of simple organic and inorganic crystals. Here we present a detailed study of the mechanism by which SAMs control the oriented nucleation by examining a more complex case of crystallization of bifunctional organic molecules. Malonic and succinic acids were grown on the SAMs of HS(CH2)10CO2H and HS(CH2)11CO2H supported on gold films. Each SAM induced a very controlled, specific orientation of the crystals. The preferred nucleating planes always exhibited an alignment of one of the carboxylic acid groups in the molecules of the growing crystal with the carboxylic acid groups on the surface of the SAMs. These results suggest that the translation of the structural information through the interface occurs by stereochemical registry such that the functional groups in the SAM play the role of an oriented surrogate layer for the nucleating crystal. These findings are very important to the understanding of the underlying principles by which various organic surfaces;and most probably also biological templates;control the crystallization process. Introduction templates to control the formation of both organic and inorganic An understanding of crystal nucleation and growth and the materials. -
Tricarboxylic Acid (TCA) Cycle Intermediates: Regulators of Immune Responses
life Review Tricarboxylic Acid (TCA) Cycle Intermediates: Regulators of Immune Responses Inseok Choi , Hyewon Son and Jea-Hyun Baek * School of Life Science, Handong Global University, Pohang, Gyeongbuk 37554, Korea; [email protected] (I.C.); [email protected] (H.S.) * Correspondence: [email protected]; Tel.: +82-54-260-1347 Abstract: The tricarboxylic acid cycle (TCA) is a series of chemical reactions used in aerobic organisms to generate energy via the oxidation of acetylcoenzyme A (CoA) derived from carbohydrates, fatty acids and proteins. In the eukaryotic system, the TCA cycle occurs completely in mitochondria, while the intermediates of the TCA cycle are retained inside mitochondria due to their polarity and hydrophilicity. Under cell stress conditions, mitochondria can become disrupted and release their contents, which act as danger signals in the cytosol. Of note, the TCA cycle intermediates may also leak from dysfunctioning mitochondria and regulate cellular processes. Increasing evidence shows that the metabolites of the TCA cycle are substantially involved in the regulation of immune responses. In this review, we aimed to provide a comprehensive systematic overview of the molecular mechanisms of each TCA cycle intermediate that may play key roles in regulating cellular immunity in cell stress and discuss its implication for immune activation and suppression. Keywords: Krebs cycle; tricarboxylic acid cycle; cellular immunity; immunometabolism 1. Introduction The tricarboxylic acid cycle (TCA, also known as the Krebs cycle or the citric acid Citation: Choi, I.; Son, H.; Baek, J.-H. Tricarboxylic Acid (TCA) Cycle cycle) is a series of chemical reactions used in aerobic organisms (pro- and eukaryotes) to Intermediates: Regulators of Immune generate energy via the oxidation of acetyl-coenzyme A (CoA) derived from carbohydrates, Responses. -
APPENDIX G Acid Dissociation Constants
harxxxxx_App-G.qxd 3/8/10 1:34 PM Page AP11 APPENDIX G Acid Dissociation Constants § ϭ 0.1 M 0 ؍ (Ionic strength ( † ‡ † Name Structure* pKa Ka pKa ϫ Ϫ5 Acetic acid CH3CO2H 4.756 1.75 10 4.56 (ethanoic acid) N ϩ H3 ϫ Ϫ3 Alanine CHCH3 2.344 (CO2H) 4.53 10 2.33 ϫ Ϫ10 9.868 (NH3) 1.36 10 9.71 CO2H ϩ Ϫ5 Aminobenzene NH3 4.601 2.51 ϫ 10 4.64 (aniline) ϪO SNϩ Ϫ4 4-Aminobenzenesulfonic acid 3 H3 3.232 5.86 ϫ 10 3.01 (sulfanilic acid) ϩ NH3 ϫ Ϫ3 2-Aminobenzoic acid 2.08 (CO2H) 8.3 10 2.01 ϫ Ϫ5 (anthranilic acid) 4.96 (NH3) 1.10 10 4.78 CO2H ϩ 2-Aminoethanethiol HSCH2CH2NH3 —— 8.21 (SH) (2-mercaptoethylamine) —— 10.73 (NH3) ϩ ϫ Ϫ10 2-Aminoethanol HOCH2CH2NH3 9.498 3.18 10 9.52 (ethanolamine) O H ϫ Ϫ5 4.70 (NH3) (20°) 2.0 10 4.74 2-Aminophenol Ϫ 9.97 (OH) (20°) 1.05 ϫ 10 10 9.87 ϩ NH3 ϩ ϫ Ϫ10 Ammonia NH4 9.245 5.69 10 9.26 N ϩ H3 N ϩ H2 ϫ Ϫ2 1.823 (CO2H) 1.50 10 2.03 CHCH CH CH NHC ϫ Ϫ9 Arginine 2 2 2 8.991 (NH3) 1.02 10 9.00 NH —— (NH2) —— (12.1) CO2H 2 O Ϫ 2.24 5.8 ϫ 10 3 2.15 Ϫ Arsenic acid HO As OH 6.96 1.10 ϫ 10 7 6.65 Ϫ (hydrogen arsenate) (11.50) 3.2 ϫ 10 12 (11.18) OH ϫ Ϫ10 Arsenious acid As(OH)3 9.29 5.1 10 9.14 (hydrogen arsenite) N ϩ O H3 Asparagine CHCH2CNH2 —— —— 2.16 (CO2H) —— —— 8.73 (NH3) CO2H *Each acid is written in its protonated form. -
Production of Succinic Acid by E.Coli from Mixtures of Glucose
2005:230 CIV MASTER’S THESIS Production of Succinic Acid by E. coli from Mixtures of Glucose and Fructose ANDREAS LENNARTSSON MASTER OF SCIENCE PROGRAMME Chemical Engineering Luleå University of Technology Department of Chemical Engineering and Geosciences Division of Biochemical and Chemical Engineering 2005:230 CIV • ISSN: 1402 - 1617 • ISRN: LTU - EX - - 05/230 - - SE Abstract Succinic acid, derived from fermentation of renewable feedstocks, has the possibility of replacing petrochemicals as a building block chemical. Another interesting advantage with biobased succinic acid is that the production does not contribute to the accumulation of CO2 to the environment. The produced succinic acid can therefore be considered as a “green” chemical. The bacterium used in this project is a strain of Escherichia coli called AFP184 that has been metabolically engineered to produce succinic acid in large quantities from glucose during anaerobic conditions. The objective with this thesis work was to evaluate whether AFP184 can utilise fructose, both alone and in mixtures with glucose, as a carbon source for the production of succinic acid. Hydrolysis of sucrose yields a mixture of fructose and glucose in equal ratio. Sucrose is a common sugar and the hydrolysate is therefore an interesting feedstock for the production of succinic acid. Fermentations with an initial sugar concentration of 100 g/L were conducted. The sugar ratios used were 100 % fructose, 100 % glucose and a mixture with 50 % fructose and glucose, respectively. The fermentation media used was a lean, low- cost media based on corn steep liquor and a minimal addition of inorganic salts. Fermentations were performed with a 12 L bioreactor and the acid and sugar concentrations were analysed with an HPLC system. -
BIO-BASED SUCCINIC ACID by Sudeep Vaswani (December 2010)
PEP Review 2010-14 BIO-BASED SUCCINIC ACID By Sudeep Vaswani (December 2010) ABSTRACT In a U.S. Department of Energy report published in 2004, succinic acid was identified as one of the top twelve building-block chemicals that could be produced from renewable feedstocks. Currently, succinic acid uses a petroleum-derived maleic anhydride route for its production, which is both costly and environmentally unfriendly. As a result, there is a growing interest towards discovering a more economical and environmentally cleaner way for its production. One methodology that has been receiving increased attention is the use of bacterial microorganisms. This technology takes advantage of the fermentative capabilities of various microorganisms and utilizes a renewable substrate as a carbon source for acid formation. Succinic acid production from microbial organisms has tremendous potential as a building block for commodity chemicals with applications in several industries. Some of the succinic acid derivatives include: tetrahydrofuran (THF), 1,4-butanediol (BDO), succindiamide, succinonitrile, dimethylsuccinate, N-methyl-pyrrolidone, 2-pyrrolidone, and 1,4-diaminobutane. This PEP Review discusses and provides a detailed techno-economic analysis for bio-based succinic acid production with a capacity of 82.7 million lb/year (37,500 mt/yr). Additionally, it covers information regarding genetic engineering mechanisms, regulation of specific enzymes, and purification of succinic acid to provide a cost-competitive alternative to fossil fuels. © SRI Consulting PEP Review 2010-14 A private report by the Process Economics Program Review No. 2010-14 BIO-BASED SUCCINIC ACID by Sudeep Vaswani December 2010 Menlo Park, California 94025 SRIC agrees to assign professionally qualified personnel to the preparation of the Process Economics Program’s reports and will perform the work in conformance with generally accepted professional standards. -
Production of Malonic Acid Through the Fermentation of Glucose
University of Pennsylvania ScholarlyCommons Department of Chemical & Biomolecular Senior Design Reports (CBE) Engineering 4-20-2018 Production of Malonic Acid through the Fermentation of Glucose Emily P. Peters University of Pennsylvania, [email protected] Gabrielle J. Schlakman University of Pennsylvania, [email protected] Elise N. Yang University of Pennsylvania, [email protected] Follow this and additional works at: https://repository.upenn.edu/cbe_sdr Part of the Biochemical and Biomolecular Engineering Commons Peters, Emily P.; Schlakman, Gabrielle J.; and Yang, Elise N., "Production of Malonic Acid through the Fermentation of Glucose" (2018). Senior Design Reports (CBE). 107. https://repository.upenn.edu/cbe_sdr/107 This paper is posted at ScholarlyCommons. https://repository.upenn.edu/cbe_sdr/107 For more information, please contact [email protected]. Production of Malonic Acid through the Fermentation of Glucose Abstract The overall process to produce malonic acid has not drastically changed in the past 50 years. The current process is damaging to the environment and costly, requiring high market prices. Lygos, Inc., a lab in Berkeley, California, has published a patent describing a way to produce malonic acid through the biological fermentation of genetically modified easty cells. This proposed technology is appealing as it is both better for the environment and economically friendly. For the process discussed in this report, genetically modified Pichia Kudriavzevii yeast cells will be purchased from the Lygos lab along with the negotiation of exclusive licensing rights to the technology. The cells will be grown in fermentation vessels, while being constantly fed oxygen, glucose and fermentation media. The cells will excrete malonic acid in the 101 hour fermentation process. -
Maleic Anhydride
Product Stewardship Summary Maleic anhydride General Statement Maleic anhydride (MAN) is an organic chemical intermediate for the manufacture of numerous products including unsaturated polyester resins (UPR), MAN-based copolymers, lube oil additives, alkyl succinic anhydrides (ASA), malic acid, fumaric acid and various agricultural chemicals. UPR’s are used in boats, automobiles, buildings, piping, and electrical goods. MAN-based copolymers consist of a wide variety of copolymers with diverse applications including compatibilizers and coupling agents with polyolefins and as thickeners, dispersants and stabilizing agents in consumer products such as cosmetics and toiletries. Lube oil additives synthesized from maleic anhydride are used to prolong oil change intervals and improve engine efficiency. ASA’s are used in a variety of applications including paper sizing, detergents, leather treatment and food products. Malic acid is primarily used as an additive to food and beverages to control pH and enhance flavors. Fumaric acid uses include paper sizing, food acidulant and UPR manufacture. Agricultural chemicals from maleic anhydride include pesticides, herbicides and growth regulators. Maleic anhydride rapidly forms maleic acid when in contact with water. This acid is an irritant and skin sensitizer. Consumer exposure to maleic anhydride is uncommon, and worker exposure is controlled by protective equipment and ventilation. Chemical Identity Name: Maleic Anhydride Brand Names: Sold as such, and incorporated into unsaturated polyester resins and food additive products Chemical name (IUPAC): furan-2,5-dione CAS number(s): 108-31-6 EC number: 203-571-6 Molecular formula: C4H2O3 Structure: Uses and Applications Ashland produces maleic anhydride in the USA. Ashland uses maleic anhydride to produce unsaturated polyester resins and food additive products. -
3.2 N-Butane to Maleic Anhydride
Alma Mater Studiorum – Università di Bologna DOTTORATO DI RICERCA IN Chimica Ciclo XXVII Settore Concorsuale di afferenza: 03/C2 Settore Scientifico disciplinare: CHIM/04 THE SYNTHESIS OF MALEIC ANHYDRIDE: STUDY OF A NEW PROCESS AND IMPROVEMENT OF THE INDUSTRIAL CATALYST Presentata da: Giulia Pavarelli Coordinatore Dottorato Relatore Prof. Aldo Roda prof. Fabrizio Cavani Esame finale anno 2015 Summary Summary 1 Aim of work ..............................................................................5 2 Introduction ...............................................................................7 2.1 Maleic anhydride .............................................................................. 7 2.2 Maleic anhydride production .......................................................... 10 2.3 Commercial Maleic Anhydride Technologies ............................... 13 2.3.1 Fixed bed .................................................................................. 14 2.3.2 Fluidized bed ............................................................................ 15 2.3.3 Transported bed ........................................................................ 16 2.4 Vanadyl pyrophosphate catalyst ..................................................... 17 2.4.1 Synthesis of the precursor VOHPO4·0.5H2O........................... 18 2.4.2 Thermal treatment of the precursor VOHPO4·0.5H2O: mechanism of transformation of VHP to VPP ..................................... 20 2.4.3 Activation of (VO)2P2O7 catalyst ............................................ -
Interpretive Guide
INTERPRETIVE GUIDE Contents INTRODUCTION .........................................................................1 NUTREVAL BIOMARKERS ...........................................................5 Metabolic Analysis Markers ....................................................5 Malabsorption and Dysbiosis Markers .....................................5 Cellular Energy & Mitochondrial Metabolites ..........................6 Neurotransmitter Metabolites ...............................................8 Vitamin Markers ....................................................................9 Toxin & Detoxification Markers ..............................................9 Amino Acids ..........................................................................10 Essential and Metabolic Fatty Acids .........................................13 Cardiovascular Risk ................................................................15 Oxidative Stress Markers ........................................................16 Elemental Markers ................................................................17 Toxic Elements .......................................................................18 INTERPRETATION-AT-A-GLANCE .................................................19 REFERENCES .............................................................................23 INTRODUCTION A shortage of any nutrient can lead to biochemical NutrEval profile evaluates several important biochemical disturbances that affect healthy cellular and tissue pathways to help determine nutrient -
Dissociation Constants of Organic Acids and Bases
DISSOCIATION CONSTANTS OF ORGANIC ACIDS AND BASES This table lists the dissociation (ionization) constants of over pKa + pKb = pKwater = 14.00 (at 25°C) 1070 organic acids, bases, and amphoteric compounds. All data apply to dilute aqueous solutions and are presented as values of Compounds are listed by molecular formula in Hill order. pKa, which is defined as the negative of the logarithm of the equi- librium constant K for the reaction a References HA H+ + A- 1. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous i.e., Solution, Butterworths, London, 1965; Supplement, 1972. 2. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids + - Ka = [H ][A ]/[HA] in Aqueous Solution, Pergamon, Oxford, 1979. 3. Albert, A., “Ionization Constants of Heterocyclic Substances”, in where [H+], etc. represent the concentrations of the respective Katritzky, A. R., Ed., Physical Methods in Heterocyclic Chemistry, - species in mol/L. It follows that pKa = pH + log[HA] – log[A ], so Academic Press, New York, 1963. 4. Sober, H.A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca that a solution with 50% dissociation has pH equal to the pKa of the acid. Raton, FL, 1968. 5. Perrin, D. D., Dempsey, B., and Serjeant, E. P., pK Prediction for Data for bases are presented as pK values for the conjugate acid, a a Organic Acids and Bases, Chapman and Hall, London, 1981. i.e., for the reaction 6. Albert, A., and Serjeant, E. P., The Determination of Ionization + + Constants, Third Edition, Chapman and Hall, London, 1984. BH H + B 7. Budavari, S., Ed., The Merck Index, Twelth Edition, Merck & Co., Whitehouse Station, NJ, 1996. -
Dl-MALIC ACID
dl-MALIC ACID Prepared at the 57th JECFA (1999) and published in FNP 52 Add 9 (2001), superseding specifications prepared at the 53rd JECFA (1999), published in FNP 52 Add 7 (1999). ADI “not specified”, established at the 13th JECFA in 1969. SYNONYMS 2-Hydroxybutanedioic acid; INS No. 296 DEFINITION Chemical names dl-Malic acid, 2-Hydroxybutanedioic acid, Hydroxysuccinic acid C.A.S. number 617-48-1 Chemical formula C4H6O5 Structural formula Formula weight 134.09 Assay Not less than 99.0% DESCRIPTION White or nearly white crystalline powder or granules FUNCTIONAL USES Acidity regulator, flavouring agent (See ‘Flavouring agents’ monograph JECFA no. 619) CHARACTERISTICS IDENTIFICATION Solubility (Vol. 4) Very soluble in water; freely soluble in ethanol Melting range (Vol. 4) 127 - 132° Test for malate (Vol. 4) Passes test Test 5 ml of a 1 in 20 solution of the sample, neutralized with ammonia TS PURITY Sulfated ash (Vol. 4) Not more than 0.1% Test 2 g of the sample (Method I) Fumaric and maleic acid Not more than 1.0% of fumaric acid and not more than 0.05% of maleic acid See description under TESTS Lead (Vol. 4) Not more than 2 mg/kg Determine using an atomic absorption technique appropriate to the specified level. The selection of sample size and method of sample preparation may be based on the principles of the method described in Volume 4, “Instrumental Methods.” TESTS PURITY TESTS Fumaric and maleic acid Buffer solution A In a 1000-ml volumetric flask dissolve 74.5 g of potassium chloride in 500 ml of water, add 100 ml of concentrated hydrochloric acid, and dilute to volume with water. -
The Toxic Effects of Oxygen on Brain Metabolism and on Tissue Enzymes 2
Vol. 40 OXYGEN POISONING OF BRAIN TISSUE 171 Meyer, A. L. (1927). Amer. J. Phy8iol. 82, 370. Reiman, C. K. & Minot, A. S. (1920). J. biol. Chem. 42, 329. Michaelis, M. & Quastel, J. H. (1941). Biochem. J. 85, 518. Schales, 0. (1938). Ber. dtsch. chem. Ge8. 71, 447. Ochoa, S. (1939). Nature, Lond., 144, 834. Sollmann, T. H. (1942). Manual of Pharmacology, 6th -ed. Ochoa, S. (1943). J. biol. Chem. 151, 493. New York: Saunders. Penfield, W. & Erickson, T. C. (1941). Epilep8y and Cerebral Soskin, S. & Taubenhaus, M. (1943). J. Pharmacol. 78, 49. Localization. London: Baillibre, Tindall and Cox. Stadie, W. C. (1943). Personal communication. Peters, R. A. (1940). Personal communication. Stadie, W. C. & Riggs, B. C. (1944). J. biol. Chem. 154, 687. Potter, V. R. & Elvehjem, C. A. (1936). J. biol. Chem. 114, Stadie, W. C., Riggs, B. C. & Haugaard, N. (1944). Amer. J. 495. med. Sci. 207, 84. Quastel, J. H. (1939). Phy8iol. Rev. 19, 135. Still, J. L. (1941). Biochem. J. 35, 380. Quastel, J. H. (1943). Personal communication. Warburg, 0. (1930). The Metabolism of Tumours (trans. Quastel, J. H. & Wheatley, A. H. M. (1932). Biochem. J. F. Dickens). London: Constable and Co. 26, 725. Weil-Malherbe, H. (1938). Biochem. J. 32, 2257. The Toxic Effects of Oxygen on Brain Metabolism and on Tissue Enzymes 2. TISSUE ENZYMES BY F. DICKENS, National In8titute for Medical Research, London, N. W. 3, and Cancer Research Laboratory, Royal Victoria Infirmary, Newcastle-upon-Tyne (Received 23 October 1945) The evidence in Part 1 (Dickens, 1946) enables the present paper, some general evidence is collected following working hypothesis of the mode of action on the mode of inactivation by oxygen ofsome other of oxygen on brain metabolism to be advanced enzymes, particularly those which, like pyruvate with some confidence.