DOCSLIB.ORG

Oxidation of Long-Chain N-Alkanes by Mutants of a Thermophilic Alkane-Degrading Bacterium: Thermus Sp. ATN1

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Oxidation of Long-Chain N-Alkanes by Mutants of a Thermophilic Alkane-Degrading Bacterium: Thermus Sp. ATN1 Oxidation of long-chain n-alkanes by mutants of a thermophilic alkane-degrading bacterium: Thermus sp. ATN1 Dem Promotionsausschuss der Technischen Universität Hamburg-Harburg zur Erlangung des akademischen Grades Doktor der Naturwissenschaften (Dr. rer. nat.) genehmigte Dissertation von José Luis García Ojeda aus Parral, Chihuahua, Mexiko 2013 Gutachter: 1. Prof. Dr. rer. nat. Rudolf Müller 2. Prof. Dr.-Ing. Wolfgang Calmano Tag der mündlichen Prüfung: 5. April 2013 TUBdok der Universitätsbibliothek der TU Hamburg-Harburg urn:nbn:de:gbv:830-tubdok-12557 Abstract In this work, mutants of the thermophilic bacterium, Thermus sp. ATN1, capable to de- grade long-chain n-alkanes at 70°C, have been constructed by classical mutagenesis. Long-chain n-alkanes were converted constitutively by these mutants to long-chain alde- hyde intermediates, mono- and dicarboxylic acids. Additionally, the gene encoding an alcohol dehydrogenase, suspected to be involved in the metabolism of long-chain n-alkanes in this strain, was disrupted by homologous re- combination in an attempt to create mutants producing terminally di-hydroxylated com- pounds. Only fatty acids were obtained. Over-oxidation of the alcohol products by the alkane monooxygenase complex in this strain or the presence of another alcohol dehy- drogenase are proposed as explanation for these results. Nevertheless, the constructed mutants were capable to produce long-chain α,ω- dicarboxylic acids with up to 28 carbon atoms by bioconversion of the corresponding n- alkanes and it is expected that saturated substrates with up to 32 carbon atoms can be converted by these mutants. This is the first known report on bioconversion of aliphatic hydrocarbons of chain lengths larger than 18 carbon atoms to mono and dicarboxylic ac- ids with a thermophilic bacterium. The broad range of long-chain diacid products obtained with these mutants could be produced for new types of polymers, adhesives, lubricant additives, pharmaceuticals and other novel applications. In addition, Thermus sp. ATN1 offers several advantages over other microorganisms for the production of long-chain α,ω-dicarboxylic acids. The strain is non-pathogenic and its thermophilic nature provides unique characteristics for process control to avoid culture contamination. Finally, the production of a biosurfactant by this thermophilic strain and its characteriza- tion are described. This biosurfactant showed advantages over commercial surfactants in the characterization tests, especially at high temperatures. The use of this biosurfactant as hydrocarbon bioavailability enhancer is demonstrated in the utilization of n- hexadecane by a mesophilic strain. Zusammenfassung In dieser Arbeit wurden Mutanten des thermophilen, Alkan-abbauenden Bakteriums Thermus sp. ATN1 durch klassische Mutagenese hergestellt. Langkettige n-Alkane wurden durch diese Mutanten zu langkettigen Aldehydezwischenprodukten, Mono- und Dicarbonsäuren konstitutiv bei 70 °C umgesetzt. Zusätzlich wurde das Gen, das für eine Alkoholdehydrogenase kodiert, durch homolge Rekombination ausgeschaltet. Dieses En- zym ist vermutlich am Abbau von langkettigen n-Alkanen in diesem Bakterienstamm be- teiligt. Diese Mutanten sollten eigentlich α,ω-di-hydroxylierte Verbindungen produzie- ren, es wurden jedoch nur Fettsäuren erhalten. Überoxidation der Alkoholprodukte durch den Alkanmonooxygenasekomplex in diesem Stamm oder das Vorhandensein einer wei- teren Alkoholdehydrogenase werden als Erklärungen für diese Ergebnisse vorgeschlagen. Dennoch waren die konstruierten Mutanten in der Lage, langkettige α,ω-Dicarbonsäuren mit bis 28 Kohlenstoffatomen durch Biokonversion der entsprechenden n-Alkane zu pro- duzieren. Es wird erwartet, dass gesättigte Substrate mit bis 32 Kohlenstoffatomen durch diese Mutanten umgesetzt werden können. Dieses ist der erste bekannte Bericht über eine Biokonversion von aliphatischen Kohlenwasserstoffen mit mehr als 18 Kohlenstoff- atomen zu den entsprechenden Mono- und Dicarbonsäuren mit einem thermophilen Bakterium. Das breite Spektrum von langkettigen α,ω-Dicarbonsäuren welche durch diese Mutanten hergestellt werden können, könnte für neue Typen von Polymeren, von Klebstoffen, von Schmierstoffadditiven, von Pharmazeutika und für andere neue Anwendungen genutzt werden. Außerdem bietet Thermus sp. ATN1 einige Vorteile über anderen Mikroorga- nismen für die Produktion von langkettigen α,ω-Dicarbonsäuren. Der Stamm ist nicht pathogen und seine thermophile Natur bietet einzigartige Vorteile für die Prozesskontrol- le, da bei hohen Temperaturen die Kontaminationswahrscheinlichkeit sehr viel geringer ist. Schließlich wurde die Produktion eines Biotensids durch diesen thermophile Stamm und dessen Charakterisierung beschrieben. Dieses Biotensid zeigte Vorteile gegenüber kom- merziellen Tensiden, besonders bei hohen Temperaturen. Die positive Wirkung dieses Biotensids zur Erhöhung der Bioverfügbarkeit und Abbaubarkeit von Kohlenwasserstof- fen, wurde am Beispiel des Abbaus von n-Hexadekan durch einen mesophilen Stamm bewiesen. Acknowledgments Many have been those that crossed my path and contributed in different but significant ways to the completion of this project. My gratitude goes to all of them. I would like to express my sincerest gratitude and appreciation to my supervisor Prof. Dr. Rudolf Müller for his invaluable support and guidance over these years, especially for trusting me the opportunity to work in his research group despite the particular circum- stances under which this research was completed. I would also like to thank Prof. Dr. Wolfgang Calmano and Prof. Dr. An-Ping Zeng for evaluating this thesis. Special thanks are also extended to Prof. Dr. Andreas Liese for supporting this work at the Institute of Technical Biocatalysis. I am also very grateful to all the colleagues I met at the Institute and in particular to those that directly contributed to this project: Maren Breuer, Pamela Vazquez and Ranganathan B. Venkatesan. Finally I would like to thank my family for their always unconditional support and in spe- cial to Dona, for her patience and encouragement during my pursuit of this Ph.D. Oxidation of long-chain n-alkanes by mutants of a thermophilic alkane-degrading bacterium: Thermus sp. ATN1 Contents 1. Introduction ........................................................................................ 13 1.1 Chemicals through biotransformation ................................................... 15 1.2 Two important industrial chemicals - Long-chain alcohols and long-chain dicarboxylic acids ........................................................................................... 17 1.2.1 Long-chain alcohols .................................................................................. 17 1.2.1.1 Applications for long-chain alcohols ................................................................ 17 1.2.1.2 Industrial production processes ...................................................................... 18 1.2.1.3 Long-chain alcohols through biocatalysis ........................................................ 20 1.2.1.3.1 Long-chain alcohols by enzymatic reduction of fatty acids ............................ 20 1.2.2 Long-chain dicarboxylic acids ................................................................... 20 1.2.2.1 Applications for long-chain dicarboxylic acids (LCDAs) .................................... 20 1.2.2.1.1 Application opportunities for LCDAs .............................................................. 21 1.2.2.2 LCDAs at industrial production scale ............................................................... 22 1.2.2.3 Industrial production processes of LCDAs ........................................................ 23 1.2.2.3.1 Cracking of vegetable oils ............................................................................... 24 1.2.2.3.2 Organic Synthesis ............................................................................................ 24 1.2.2.3.3 Biotransformation of paraffins and fatty acids .............................................. 25 1.2.2.4 Competing production processes .................................................................... 26 1.2.2.5 LCDAs through biotransformation - Process development .............................. 27 1.2.2.5.1 Biocatalyst improvement ................................................................................ 28 1.2.2.5.2 Bioprocess economics and optimization for successful development ........... 29 1.3 Bacterial long-chain alkane metabolism - Biocatalytic application for the production of chemicals ................................................................................. 33 1.3.1 Alkanes .................................................................................................... 33 1.3.2 Degradation of long-chain n-alkanes ........................................................ 33 1.3.2.1 Microbial uptake of long-chain n-alkanes as a carbon and energy source ........ 34 1.3.2.2 Bacterial aerobic n-alkane degradation pathways ........................................... 35 1 1.3.2.3 Regulation of bacterial n-alkane catabolic pathways ....................................... 37 1.3.2.3.1 Differential regulation of multiple alkane hydroxylases ................................ 38 1.3.2.3.2 Product repression ......................................................................................... 39 1.3.2.3.3 Catabolite repression ...................................................................................... 39
Load more

Recommended publications
  • Alkyldihydropyrones, New Polyketides Synthesized by a Type III Polyketide Synthase from Streptomyces Reveromyceticus
    The Journal of Antibiotics (2014) 67, 819–823 & 2014 Japan Antibiotics Research Association All rights reserved 0021-8820/14 www.nature.com/ja ORIGINAL ARTICLE Alkyldihydropyrones, new polyketides synthesized by a type III polyketide synthase from Streptomyces reveromyceticus Teruki Aizawa1, Seung-Young Kim1, Shunji Takahashi2,3, Masahiko Koshita1, Mioka Tani1, Yushi Futamura3, Hiroyuki Osada2,3 and Nobutaka Funa1 Genome sequencing allows a rapid and efficient identification of novel catalysts that produce novel secondary metabolites. Here we describe the catalytic properties of dihydropyrone synthase A (DpyA), a novel type III polyketide synthase encoded in a linear plasmid of Streptomyces reveromyceticus. Heterologous expression of dpyA led to the accumulation of alkyldihydropyrones A (1), B (2), C (3) and D (4), which are novel dihydropyran compounds that exhibit weak cytotoxicity against the leukemia cell line HL-60. DpyA catalyzes the condensation of b-hydroxyl acid thioester and methylmalonyl-CoA to yield a triketide intermediate that then undergoes lactonization of a secondary alcohol and a thioester to give alkyldihydropyrone. The Journal of Antibiotics (2014) 67, 819–823; doi:10.1038/ja.2014.80; published online 2 July 2014 INTRODUCTION Very recently, Tang et al.11 discovered that presulficidin, which is Type III polyketide synthase (PKS), which is widely distributed synthesized by Cpz6, a type III PKS from the caprazamycin among higher plants, fungi and bacteria, catalyzes the assembly of biosynthetic cluster, relays sulfonate from 30-phosphoadenine-50- primary metabolites such as acyl-CoA compounds to synthesize phosphosulfate to caprazamycin. structurally complex polyketides.1 The reaction catalyzed by type III Genome sequence analyses of Streptomyces species have shown that PKS starts with the formation of a thioester bond between the the number of biosynthetic gene clusters encoded on the chromosome catalytic center cysteine and an acyl group derived from a starter is much higher than the number of secondary metabolites isolated substrate.
    [Show full text]
  • The Reaction of Aminonitriles with Aminothiols: a Way to Thiol-Containing Peptides and Nitrogen Heterocycles in the Primitive Earth Ocean
    life Article The Reaction of Aminonitriles with Aminothiols: A Way to Thiol-Containing Peptides and Nitrogen Heterocycles in the Primitive Earth Ocean Ibrahim Shalayel , Seydou Coulibaly, Kieu Dung Ly, Anne Milet and Yannick Vallée * Univ. Grenoble Alpes, CNRS, Département de Chimie Moléculaire, Campus, F-38058 Grenoble, France; [email protected] (I.S.); [email protected] (S.C.); [email protected] (K.D.L.); [email protected] (A.M.) * Correspondence: [email protected] Received: 28 September 2018; Accepted: 18 October 2018; Published: 19 October 2018 Abstract: The Strecker reaction of aldehydes with ammonia and hydrogen cyanide first leads to α-aminonitriles, which are then hydrolyzed to α-amino acids. However, before reacting with water, these aminonitriles can be trapped by aminothiols, such as cysteine or homocysteine, to give 5- or 6-membered ring heterocycles, which in turn are hydrolyzed to dipeptides. We propose that this two-step process enabled the formation of thiol-containing dipeptides in the primitive ocean. These small peptides are able to promote the formation of other peptide bonds and of heterocyclic molecules. Theoretical calculations support our experimental results. They predict that α-aminonitriles should be more reactive than other nitriles, and that imidazoles should be formed from transiently formed amidinonitriles. Overall, this set of reactions delineates a possible early stage of the development of organic chemistry, hence of life, on Earth dominated by nitriles and thiol-rich peptides (TRP). Keywords: origin of life; prebiotic chemistry; thiol-rich peptides; cysteine; aminonitriles; imidazoles 1. Introduction In ribosomes, peptide bonds are formed by the reaction of the amine group of an amino acid with an ester function.
    [Show full text]
  • The Relative Rates of Thiol–Thioester Exchange and Hydrolysis for Alkyl and Aryl Thioalkanoates in Water
    Orig Life Evol Biosph (2011) 41:399–412 DOI 10.1007/s11084-011-9243-4 PREBIOTIC CHEMISTRY The Relative Rates of Thiol–Thioester Exchange and Hydrolysis for Alkyl and Aryl Thioalkanoates in Water Paul J. Bracher & Phillip W. Snyder & Brooks R. Bohall & George M. Whitesides Received: 14 April 2011 /Accepted: 16 June 2011 / Published online: 5 July 2011 # Springer Science+Business Media B.V. 2011 Abstract This article reports rate constants for thiol–thioester exchange (kex), and for acid- mediated (ka), base-mediated (kb), and pH-independent (kw) hydrolysis of S-methyl thioacetate and S-phenyl 5-dimethylamino-5-oxo-thiopentanoate—model alkyl and aryl thioalkanoates, respectively—in water. Reactions such as thiol–thioester exchange or aminolysis could have generated molecular complexity on early Earth, but for thioesters to have played important roles in the origin of life, constructive reactions would have needed to compete effectively with hydrolysis under prebiotic conditions. Knowledge of the kinetics of competition between exchange and hydrolysis is also useful in the optimization of systems where exchange is used in applications such as self-assembly or reversible binding. For the alkyl thioester S-methyl thioacetate, which has been synthesized in −5 −1 −1 −1 −1 −1 simulated prebiotic hydrothermal vents, ka = 1.5×10 M s , kb = 1.6×10 M s , and −8 −1 kw = 3.6×10 s . At pH 7 and 23°C, the half-life for hydrolysis is 155 days. The second- order rate constant for thiol–thioester exchange between S-methyl thioacetate and 2- −1 −1 sulfonatoethanethiolate is kex = 1.7 M s .
    [Show full text]
  • Dibasic Acids for Nylon Manufacture
    - e Report No. 75 DIBASIC ACIDS FOR NYLON MANUFACTURE by YEN-CHEN YEN October 1971 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA CONTENTS INTRODUCTION, ....................... 1 SUMMARY .......................... 3 General Aspects ...................... 3 Technical Aspects ..................... 7 INDUSTRY STATUS ...................... 15 Applications and Consumption of Sebacic Acid ........ 15 Applications and Consumption of Azelaic Acid ........ 16 Applications of Dodecanedioic and Suberic Acids ...... 16 Applications of Cyclododecatriene and Cyclooctadiene .... 17 Producers ......................... 17 Prices ........................... 18 DIBASIC ACIDS FOR MANUFACTURE OF POLYAMIDES ........ 21 CYCLOOLIGOMERIZATIONOF BUTADIENE ............. 29 Chemistry ......................... 29 Ziegler Catalyst ..................... 30 Nickel Catalyst ..................... 33 Other Catalysts ..................... 34 Co-Cyclooligomerization ................. 34 Mechanism ........................ 35 By-products and Impurities ................ 37 Review of Processes .................... 38 A Process for Manufacture of Cyclododecatriene ....... 54 Process Description ................... 54 Process Discussion .................... 60 Cost Estimates ...................... 60 A Process for Manufacture of Cyclooctadiene ........ 65 Process Description ................... 65 Process Discussion .................... 70 Cost Estimates ...................... 70 A Process for Manufacture of Cyclodecadiene
    [Show full text]
  • Transparent Amorphous Polyamides Based on Diamines and on Tetradecanedioic Acid
    Europäisches Patentamt *EP001595907A1* (19) European Patent Office Office européen des brevets (11) EP 1 595 907 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.7: C08G 69/02, C08G 69/26, 16.11.2005 Bulletin 2005/46 C08L 77/00, C08L 77/06 (21) Application number: 05290988.4 (22) Date of filing: 09.05.2005 (84) Designated Contracting States: • Bussi, Philippe AT BE BG CH CY CZ DE DK EE ES FI FR GB GR 78000 Versailles (FR) HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR • Blondel, Philippe Designated Extension States: 27300 Bernay (FR) AL BA HR LV MK YU (74) Representative: Neel, Henry (30) Priority: 14.05.2004 FR 0405259 ARKEMA Département Propriété Industrielle (71) Applicant: Arkema 4-8, cours Michelet, 92800 Puteaux (FR) La Défense 10 92091 Paris La Défense Cedex (FR) (72) Inventors: • Linemann, Annett 27550 Nassandres (FR) (54) Transparent amorphous polyamides based on diamines and on tetradecanedioic acid (57) The present invention relates to a transparent prising, by weight, 1 to 100% of the preceding polyamide amorphous polyamide which results from the conden- and 99 to 0% of a semicrystalline polyamide. sation: The invention also relates to the objects composed of the composition of the invention, such as panels, • of at least one diamine chosen from aromatic, ary- films, sheets, pipes, profiles or objects obtained by in- laliphatic and cycloaliphatic diamines, jection moulding. • of tetradecanedioic acid or of a mixture comprising The invention also relates to objects covered with a at least 50 mol% of tetradecanedioic acid and at transparent protective layer composed of the composi- least one diacid chosen from aliphatic, aromatic and tion of the invention.
    [Show full text]
  • Identification of a Thioesterase Bottleneck in the Pikromycin Pathway Through Full-Module Processing of Unnatural Pentaketides
    Article pubs.acs.org/JACS Identification of a Thioesterase Bottleneck in the Pikromycin Pathway through Full-Module Processing of Unnatural Pentaketides † ‡ † § † ‡ ⊥ ∥ Douglas A. Hansen, , Aaron A. Koch, , and David H. Sherman*, , , , † ‡ § ⊥ Life Sciences Institute, Department of Medicinal Chemistry, Cancer Biology Graduate Program, Department of Chemistry, and ∥ Department of Microbiology & Immunology, University of Michigan, Ann Arbor, Michigan 48109, United States *S Supporting Information ABSTRACT: Polyketide biosynthetic pathways have been engineered to generate natural product analogs for over two decades. However, manipulation of modular type I polyketide synthases (PKSs) to make unnatural metabolites commonly results in attenuated yields or entirely inactive pathways, and the mechanistic basis for compromised production is rarely elucidated since rate-limiting or inactive domain(s) remain unidentified. Accordingly, we synthesized and assayed a series of modified pikromycin (Pik) pentaketides that mimic early pathway engineering to probe the substrate tolerance of the PikAIII-TE module in vitro. Truncated pentaketides were processed with varying efficiencies to corresponding macrolactones, while pentaketides with epimerized chiral centers were poorly processed by PikAIII-TE and failed to generate 12-membered ring products. Isolation and identification of extended but prematurely offloaded shunt products suggested that the Pik thioesterase (TE) domain has limited substrate flexibility and functions as a gatekeeper in the processing of
    [Show full text]
  • Using Dynamic Combinatorial Chemistry to Construct Novel Thioester and Disulfide Lipids
    Using dynamic combinatorial chemistry to construct novel thioester and disulfide lipids A dissertation submitted to the University of Manchester for the degree of MSc by Research Chemistry In the Faculty of Science and Engineering 2017 Jack A. Yung School of Chemistry Table of Contents List of figures, tables and equations 5 Symbols and abbreviations 10 Abstract 12 Declaration 13 Copyright statement 13 Acknowledgements 14 The author 14 Chapter 1. Introduction 15 1.1 The cell membrane 16 1.1.1 Function and composition 16 1.2 Membrane lipids 16 1.2.1 Lipid classification 16 1.2.2 Amphiphiles 17 1.2.3 Glycolipids 17 1.2.4 Sterols 18 1.2.5 Phospholipids 19 1.3 Lipid vesicles 20 1.3.1 Supramolecular self-assembly 20 1.3.2 Interaction free energies 21 1.3.3 Framework for the theory of self-assembly 22 1.3.4 Micelles 23 1.3.5 Lipid bilayers 24 1.3.6 Vesicles 25 1.3.7 Phase-transition temperature 27 1.4 Amphiphilic building blocks 27 1.5 Thioesters 29 1.5.1 Thioester reactivity 29 1.5.2 Trans-thioesterification 30 1.5.3 Thioester exchange reactions in DCC 31 1.6 Disulfides 32 2 1.6.1 Disulfide reactivity 32 1.6.2 Thiol-disulfide interchange reactions 32 1.6.3 Disulfide exchange reactions in DCC 33 1.7 Pre-biotic lipids 34 1.7.1 Sources of pre-biotic organic compounds 34 1.7.2 The first pre-biotic membrane structure 36 1.7.3 The role of sulfur in pre-biotic chemistry 36 1.8 Artificially designed vesicles 37 1.8.1 Applications of artificially designed vesicles 37 1.8.2 Zeta-potential 37 1.8.3 Vesicle design 38 1.9 Targets 39 1.9.1 Aims 39 Chapter 2.
    [Show full text]
  • Variations in the Structure and Reactivity of Thioester Functionalized Self-Assembled Monolayers and Their Use for Controlled Surface Modification
    Variations in the structure and reactivity of thioester functionalized self-assembled monolayers and their use for controlled surface modification Inbal Aped, Yacov Mazuz and Chaim N. Sukenik* Full Research Paper Open Access Address: Beilstein J. Nanotechnol. 2012, 3, 213–220. Department of Chemistry and Institute for Nanotechnology and doi:10.3762/bjnano.3.24 Advanced Materials, Bar-Ilan University, Ramat-Gan, Israel 52900 Received: 01 December 2011 Email: Accepted: 10 February 2012 Chaim N. Sukenik* - [email protected] Published: 09 March 2012 * Corresponding author This article is part of the Thematic Series "Self-assembly at solid surfaces". Keywords: siloxane-anchored self-assembled monolayers; sulfonated interfaces; Guest Editors: S. R. Cohen and J. Sagiv surface chemistry © 2012 Aped et al; licensee Beilstein-Institut. License and terms: see end of document. Abstract Thioester-functionalized, siloxane-anchored, self-assembled monolayers provide a powerful tool for controlling the chemical and physical properties of surfaces. The thioester moiety is relatively stable to long-term storage and its structure can be systematically varied so as to provide a well-defined range of reactivity and wetting properties. The oxidation of thioesters with different-chain- length acyl groups allows for very hydrophobic surfaces to be transformed into very hydrophilic, sulfonic acid-bearing, surfaces. Systematic variation in the length of the polymethylene chain has also allowed us to examine how imbedding reaction sites at various depths in a densely packed monolayer changes their reactivity. π-Systems (benzene and thiophene) conjugated to the thioester carbonyl enable the facile creation of photoreactive surfaces that are able to use light of different wavelengths.
    [Show full text]
  • 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.
    [Show full text]
  • 215-216 HH W12-Notes-Ch 15
    Chem 215 F12 Notes Notes – Dr. Masato Koreeda - Page 1 of 17. Date: October 5, 2012 Chapter 15: Carboxylic Acids and Their Derivatives and 21.3 B, C/21.5 A “Acyl-Transfer Reactions” I. Introduction Examples: note: R could be "H" R Z R O H R O R' ester O carboxylic acid O O an acyl group bonded to R X R S acid halide* R' an electronegative atom (Z) thioester O X = halogen O R' R, R', R": alkyl, alkenyl, alkynyl, R O R' R N or aryl group R" amide O O O acid anhydride one of or both of R' and R" * acid halides could be "H" R F R Cl R Br R I O O O O acid fluoride acid chloride acid bromide acid iodide R Z sp2 hybridized; trigonal planar making it relatively "uncrowded" O The electronegative O atom polarizes the C=O group, making the C=O carbon "electrophilic." Resonance contribution by Z δ * R Z R Z R Z R Z C C C C O O O δ O hybrid structure The basicity and size of Z determine how much this resonance structure contributes to the hybrid. * The more basic Z is, the more it donates its electron pair, and the more resonance structure * contributes to the hybrid. similar basicity O R' Cl OH OR' NR'R" Trends in basicity: O weakest increasing basiciy strongest base base Check the pKa values of the conjugate acids of these bases. Chem 215 F12 Notes Notes –Dr. Masato Koreeda - Page 2 of 17.
    [Show full text]
  • Federal Register / Vol. 60, No. 123 / Tuesday, June 27, 1995 / Notices 33203
    Federal Register / Vol. 60, No. 123 / Tuesday, June 27, 1995 / Notices 33203 Chemical Substances Removed from the TSCA Inventory CASRN CAS Index Name 67989±80±4 1,3-Benzenedicarboxylic acid, polymer with 2-(dimethylamino)ethanol, 2,2-dimethyl-1,3- propanediol, 2,2-dimethylpropanoic acid and nonanedioic acid 68002±78±8 Fatty acids, C16-18 and C18-unsatd., triesters with trimethylolpropane 68479±21±0 Poly(oxy-1,2-ethanediyl), α-hydro-ω-hydroxy-, ether with N-[2-[bis(2- hydroxyethyl)methylammonio]ethyl]-N,N'-bis(2-hydroxyethyl)-N'-[2-hydroxy-3-(9- octadecenyloxy)propyl]-N,N'-dimethyl-1,2-ethanediaminium tris(methyl sulfate) (4:1), (Z)- 68551±46±2 Carboxylic acids, C6-18 and C9-15-di-, polymers with adipic acid, ethylene glycol, glutaric acid and succinic acid, 2-ethylhexyl esters 68607±79±4 Silica gel, reaction products with chlorodimethyloctylsilane 68610±78±6 Acetic acid, anhydride, reaction products with boron trifluoride and 1,5,9-trimethyl-1,5,9- cyclododecatriene 68814±84±6 Fatty acids, tall-oil, polymers with isophthalic acid and 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazine- 2,4,6(1H,3H,5H)-trione 68958±73±6 Hexanedioic acid, polymer with 1,6-diisocyanato-2,2,4-trimethylhexane, oxybis[propanol] and α,α',α''-1,2,3-propanetriyltris[ω-hydroxypoly[oxy(methyl-1,2-ethanediyl)]] 70528±75±5 Cashew, nutshell liq., polymer with formaldehyde, linseed oil and phenol 71243±48±6 Amines, C14-18 and C16-18-unsatd. alkyl, ethoxylated, compds. with polyethylene glycol mono(nonylphenyl) ether phosphate 71735±58±5 Chromate(2-), [1-[(5-chloro-2-hydroxyphenyl)azo]-2-naphthalenolato(2-)][3-hydroxy-4-[(2- hydroxy-3,5-dinitrophenyl)azo]-7-[(4-methoxyphenyl)amino]-2-naphthalenesulfonato(3-)]-, disodium 71735±65±4 Cuprate(4-), [8-hydroxy-7-[[2-hydroxy-7-sulfo-6-[[4-[(2,5,6-trichloro-4- pyrimidinyl)amino]phenyl]azo]-1-naphthalenyl]azo]-1,3,6-naphthalenetrisulfonato(6-)]-, tetrasodium 72245±32±0 Propanoic acid, 2-hydroxy-, compds.
    [Show full text]
  • Linear Alpha-Olefins (681.5030)
    IHS Chemical Chemical Economics Handbook Linear alpha-Olefins (681.5030) by Elvira O. Camara Greiner with Yoshio Inoguchi Sample Report from 2010 November 2010 ihs.com/chemical November 2010 LINEAR ALPHA-OLEFINS Olefins 681.5030 B Page 2 The information provided in this publication has been obtained from a variety of sources which SRI Consulting believes to be reliable. SRI Consulting makes no warranties as to the accuracy completeness or correctness of the information in this publication. Consequently SRI Consulting will not be liable for any technical inaccuracies typographical errors or omissions contained in this publication. This publication is provided without warranties of any kind either express or implied including but not limited to implied warranties of merchantability fitness for a particular purpose or non-infringement. IN NO EVENT WILL SRI CONSULTING BE LIABLE FOR ANY INCIDENTAL CONSEQUENTIAL OR INDIRECT DAMAGES (INCLUDING BUT NOT LIMITED TO DAMAGES FOR LOSS OF PROFITS BUSINESS INTERRUPTION OR THE LIKE) ARISING OUT OF THE USE OF THIS PUBLICATION EVEN IF IT WAS NOTIFIED ABOUT THE POSSIBILITY OF SUCH DAMAGES. BECAUSE SOME STATES DO NOT ALLOW THE EXCLUSION OR LIMITATION OF LIABILITY FOR CONSEQUENTIAL OR INCIDENTAL DAMAGES THE ABOVE LIMITATION MAY NOT APPLY TO YOU. IN SUCH STATES SRI CONSULTING’S LIABILITY IS LIMITED TO THE MAXIMUM EXTENT PERMITTED BY SUCH LAW. Certain statements in this publication are projections or other forward-looking statements. Any such statements contained herein are based upon SRI Consulting’s current knowledge and assumptions about future events including without limitation anticipated levels of global demand and supply expected costs trade patterns and general economic political and marketing conditions.
    [Show full text]