DOCSLIB.ORG

United States Patent (19) (11 Patent Number: 4859,592 Hagedorn Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) (11 Patent Number: 4859,592 Hagedorn Et Al United States Patent (19) (11 Patent Number: 4859,592 Hagedorn et al. 45 Date of Patent: Aug. 22, 1989 54 PRODUCTION OF PICOL.INIC ACID AND OTHER PUBLICATIONS PYRIDINE PRODUCTS VIA PSEUDOMONAS Dagley, et al., "New Pathways in the Oxidative Metab olism of Aromatic Compounds by Micro-Organisms'; (76 Inventors: Scott R. Hagedorn, Old Coach Rd., Summit, N.J. 07087; Anthony J. East, Nature, V. 188, pp. 560-566 (1960). 63 Niles Ave., Madison, N.J. O7940; Moser et al., “Decarboxylation of 5-Sub Sol J. Barer, 271 White Oak Ridge stituted-2-Pyridinecarboxylic Acids', J. Org. Chem., Rd., Bridgewater, N.J. 08807 V. 37, No. 24, pp. 3938-3940 (1972). Primary Examiner-Elizabeth C. Weimar 21) Appl. No.: 759,038 Attorney, Agent, or Firm-Mathews, Woodbridge, 22 Filed: Jul. 26, 1985 Goebel, Pugh & Collins (51) Int. Cl." ........................ C12P 17/12; C12N 1/20; (57) ABSTRACT C12R 1/40 (52) U.S. Cl. ................................. 435/122; 435/253.3; This invention provides a process for the bioconversion 435/877 of a non-growth aromatic feed to an accumulated quan tity of a picolinic acid product with reduced accumula (58) Field of Search ............. 435/122, 253, 877, 253.3 tion of 2-hydroxymuconic semialdehyde, and con 56 References Cited ducted in the presence of ammonium or a primary U.S. PATENT DOCUMENTS amine, which acid subsequently can be converted by 4,654,303 3/1987 Hagedorn ......................... 435/1723 chemical means to a pyridine product. 4,666,841 5/1987 Hagedorn ... ... 435/122 4,673,646 6/1987 Hagedorn ............ was sex as a was u + 435/146 6 Claims, 2 Drawing Sheets U.S. Patent Aug. 22, 1989 Sheet 1 of 2 4859592 6THTº OINITOOldNOIIVT?hW000VOIOVENEQTOLWOMJ-E 4. 4,859,592 1. 2 ultraviolet absorption spectrum indicates a 2-hydrox PRODUCTION OF PICOLINIC ACID AND ymuconic semialdehyde type product, which on stand PYRIDINE PRODUCTS WIA PSEUDOMONAS ing with ammonium hydroxide forms alpha-picolinic acid. BACKGROUND OF THE INVENTION 5 The Canadian Journal Of Microbiology, 14, Heterocyclic compounds such as pyridine currently 1005(1968) article by R. S. Davis et al describes the are recovered as constituents of coal tar, or are synthe metabolism of p-xylene and m-xylene by species of sized for example by the reaction of acetaldehyde with Pseudomonas. A metabolite is produced by a solution of ammonia and formaldehyde to provide a pyridine, al enzyme which has an ultraviolet spectrum consistent pha-picoline and beta-picoline product mixture. Spe O with 2-hydroxymuconic semialdehyde structure. A cialty heterocyclic aromatic chemicals are utilized in solution of this metabolite treated with ammonium hy the production of adhesives, pesticides, vitamins, and droxide yields a picolinic acid type product. the like. Another prospective route to heterocyclic The Biochemical Journal, 106,859(1968) publication aromatic compounds is by the reaction of ammonia or a by R. B. Cain et all also describes the formation of 5 primary amine with a 2-hydroxymuconic semialdehyde 15 methylpicolinic acid from 4-methylcatechol via 2 to form a picolinic acid: hydroxy-5-methylmuconic semialdehyde, utilizing a cell extract prepared from a microorganism grown on OH OH toluene sulfonate. The Journal Of Bacteriology, 120(1), 31(1974) publi a COH a COH NH3 cation by G. J. Wigmore et al describes Pseudomonas C - Ge. putida mutants which metabolize phenol and cresols by RSCHO NCHO the meta pathway via catechol and 2-hydroxymuconic semialdehyde intermediates. One mutant strain is de R 25 scribed as being defective in both 2-hydroxymuconic CO2H CO2H semialdehyde hydrolase and dehydrogenase. The potential of microbiological oxidation of an aro 21 N a matic substrate such as toluene as a convenient source O of 2-hydroxymuconic semialdehyde requires the con R N S struction of mutant strains of microorganisms which (1) 30 metabolize an aromatic substrate via catechol or substi R tuted catechol by means of the meta (catechol 2,3- OH OH oxygenase) pathway, and (2) allow the accumulation of a 2-hydroxymuconic semialdehyde type metabolite 21COH a coh RNH2 without its further assimilation to other metabolites. A Or - 2-Ge. 35 solution of accumulated 2-hydroxymuconic semialde RNCHO NCHO hyde metabolite is susceptible to chemical conversion to picolinic acid and pyridine products as illustrated R above. CO2H CO2H 40 Accordingly, it is an object of this invention to pro vide a procedure for the bioconversion of an aromatic 21 -R 21 N-R hydrocarbon by the meta pathway to 2-hydroxymu O conic semialdehyde or substituted 2-hydroxymuconic R S N semialdehyde, and for the in situ formation of a pico 45 linic acid product. R It is another object of this invention to provide a Subsequent decarboxylation of the picolinic acid could microbial culture which is capable of metabolizing tolu provide the corresponding pyridines and substituted ene, substituted toluene, catechol, or substituted cate pyridines, as illustrated in the Journal of Organic Chem chol to 2-hydroxymuconic semialdehyde or substituted istry, 37(24), 3938(1972) article by R. J. Moser et al. 50 2-hydroxymuconic semialdehyde metabolite quantita A potentially convenient source of 2-hydroxymu tively. conic semialdehyde is by the microbiological oxidation It is another object of this invention to provide a of various hydrocarbon substrates. Microbiological process for the synthesis of a picolinic acid product oxidation of aromatic substrates is reviewed by S. Dag from an aromatic hydrocarbon via a biosynthesized ley in Advances in Microbial Physiology, 6, 1-47(1971); 55 2-hydroxymuconic semialdehyde intermediate. by P. Chapman in "Degradation of Synthetic Organic It is a further object of this invention to provide a Molecules In The Biosphere', pages 17-55, National process for the synthesis of a pyridine product from an Academy Of Sciences, 1972; and by P. Williams in aromatic hydrocarbon via 2-hydroxymuconic semialde "Microbial Degradation Of Xenobiotics And Recalci hyde and picolinic acid intermediates. trant Compounds' pages 97-107, Academic Press, 1981. The present invention subject matter is related to that Strains of microorganisms are known which metabolize described in U.S. Pat. No. 4,666,841. aromatic hydrocarbon substrates by the meta pathway Other objects and advantages of the present invention via catechol and 2-hydroxymuconic semialdehyde to shall become apparent from the accompanying descrip biomass and carbon dioxide. tion and examples. The Nature, 188,560(1960) article by S. Dagley et al 65 describes the cleavage of catechol by a solution of an DESCRIPTION OF THE INVENTION enzyme, catechol 2,3-oxygenase, to produce a product One or more objects of the present invention are with a yellow color in the bioconversion medium. The accomplished by the provision of a process for the pro 4,859,592 3 4. duction of a picolinic acid product which comprises supplying (1) toluene or substituted toluene, (2) molecu CO2H CO2H lar oxygen, and (3) ammonia or a primary amine to a H 21 N H 2N N-R bioconversion medium containing a microbial culture o which possesses active catechol 2,3-oxygenase and R-N R R-st R which exhibits no enzymatic activity that metabolizes 2-hydroxymuconic semialdehyde or substituted 2 R R hydroxymuconic semialdehyde, to produce and accu 10 where R is as previously defined, and R1 is a substituent mulate a picolinic acid product. selected from aliphatic, alicyclic and aromatic groups. As further described herein, an alternative preferred In another embodiment, this invention provides a type of non-growth carbon source is catechol or substi process for the production of a picolinic acid product tuted catechol. The catechol chemical structure corre which comprises supplying (1) a dihydric phenol corre sponds to one of the intermediate metabolites formed 15 sponding to the formula: when toluene or substituted toluene is bioconverted by a present invention microorganism to 2-hydroxymu OH conic semialdehyde via the meta metabolic pathway. Toluene is oxidized to 2-hydroxymuconic semialdehyde 20 OH via a series of benzyl alcohol, benzaldehyde, benzoic acid, hydrodihydroxybenzoic acid and catechol inter mediates. The active enzymes include toluene monoox R ygenase, benzyl alcohol dehydrogenase, benzaldehyde dehydrogenase, benzoic acid dioxygenase, hydrodihy 25 where R is hydrogen or an alkyl group containing be droxybenzoic acid dehydrogenase and catechol 2,3- tween about 1-4 carbon atoms, (2) molecular oxygen, OXygenase. and (3) ammonia or a Rl-NH2 primary amine to a In another embodiment, this invention provides a bioconversion medium containing a microbial culture of process for the production of a picolinic acid product 30 a strain which has been constructed to possess catechol 2,3-oxygenase with activity that is not inhibited in the which comprises supplying (1) catechol or substituted presence of less than about 0.1 gram of 2-hydroxymu catechol, (2) molecular oxygen, and (3) ammonia or a conic semialdehyde per liter of bioconversion medium, primary amine to a bioconversion medium containing a and which lacks active catechol 1,2-oxygenase, 2 microbial culture which possesses active catechol 2,3- 35 hydroxymuconic semialdehyde hydrolase and 2 oxygenase and which exhibits no enzymatic activity hydroxymuconic semialdehyde dehydrogenase, to pro that metabolizes 2-hydroxymuconic semialdehyde or duce and accumulate a picolinic acid product corre substituted 2-hydroxymuconic semialdehyde, to pro sponding to the formula: duce and accumulate a picolinic acid product. In another embodiment, this invention
Load more

Recommended publications
  • CHAPTER 29 ORGANIC CHEMICALS VI 29-1 Notes 1
    )&f1y3X CHAPTER 29 ORGANIC CHEMICALS VI 29-1 Notes 1. Except where the context otherwise requires, the headings of this chapter apply only to: (a) Separate chemically defined organic compounds, whether or not containing impurities; (b) Mixtures of two or more isomers of the same organic compound (whether or not containing impurities), except mixtures of acyclic hydrocarbon isomers (other than stereoisomers), whether or not saturated (chapter 27); (c) The products of headings 2936 to 2939 or the sugar ethers and sugar esters, and their salts, of heading 2940, or the products of heading 2941, whether or not chemically defined; (d) Products mentioned in (a), (b) or (c) above dissolved in water; (e) Products mentioned in (a), (b) or (c) above dissolved in other solvents provided that the solution constitutes a normal and necessary method of putting up these products adopted solely for reasons of safety or for transport and that the solvent does not render the product particularly suitable for specific use rather than for general use; (f) The products mentioned in (a), (b), (c), (d) or (e) above with an added stabilizer (including an anticaking agent) necessary for their preservation or transport; (g) The products mentioned in (a), (b), (c), (d), (e) or (f) above with an added antidusting agent or a coloring or odoriferous substance added to facilitate their identification or for safety reasons, provided that the additions do not render the product particularly suitable for specific use rather than for general use; (h) The following products, diluted to standard strengths, for the production of azo dyes: diazonium salts, couplers used for these salts and diazotizable amines and their salts.
    [Show full text]
  • Inventory Size (Ml Or G) 103220 Dimethyl Sulfate 77-78-1 500 Ml
    Inventory Bottle Size Number Name CAS# (mL or g) Room # Location 103220 Dimethyl sulfate 77-78-1 500 ml 3222 A-1 Benzonitrile 100-47-0 100ml 3222 A-1 Tin(IV)chloride 1.0 M in DCM 7676-78-8 100ml 3222 A-1 103713 Acetic Anhydride 108-24-7 500ml 3222 A2 103714 Sulfuric acid, fuming 9014-95-7 500g 3222 A2 103723 Phosphorus tribromide 7789-60-8 100g 3222 A2 103724 Trifluoroacetic acid 76-05-1 100g 3222 A2 101342 Succinyl chloride 543-20-4 3222 A2 100069 Chloroacetyl chloride 79-04-9 100ml 3222 A2 10002 Chloroacetyl chloride 79-04-9 100ml 3222 A2 101134 Acetyl chloride 75-36-5 500g 3222 A2 103721 Ethyl chlorooxoacetate 4755-77-5 100g 3222 A2 100423 Titanium(IV) chloride solution 7550-45-0 100ml 3222 A2 103877 Acetic Anhydride 108-24-7 1L 3222 A3 103874 Polyphosphoric acid 8017-16-1 1kg 3222 A3 103695 Chlorosulfonic acid 7790-94-5 100g 3222 A3 103694 Chlorosulfonic acid 7790-94-5 100g 3222 A3 103880 Methanesulfonic acid 75-75-2 500ml 3222 A3 103883 Oxalyl chloride 79-37-8 100ml 3222 A3 103889 Thiodiglycolic acid 123-93-3 500g 3222 A3 103888 Tetrafluoroboric acid 50% 16872-11-0 1L 3222 A3 103886 Tetrafluoroboric acid 50% 16872-11-0 1L 3222 A3 102969 sulfuric acid 7664-93-9 500 mL 2428 A7 102970 hydrochloric acid (37%) 7647-01-0 500 mL 2428 A7 102971 hydrochloric acid (37%) 7647-01-0 500 mL 2428 A7 102973 formic acid (88%) 64-18-6 500 mL 2428 A7 102974 hydrofloric acid (49%) 7664-39-3 500 mL 2428 A7 103320 Ammonium Hydroxide conc.
    [Show full text]
  • Control of Growth by Picolinic Acid
    Proc. Nati. Acad. Sci. USA Vol. 74, No. 7, pp. 2889-2893, July 1977 Cell Biology Control of growth by picolinic acid: Differential response of normal and transformed cells (cell synchrony/chelating agents/NAD+/pyridine derivatives/viral transformation) J. A. FERNANDEZ-POL*t, VINCENT H. BONO, JR.J, AND GEORGE S. JOHNSON* * Laboratory of Molecular Biology and * Laboratory of Medicinal Chemistry and Biology, National Cancer Institute, Bethesda, Maryland 20014 Communicated by Nathan 0. Kaplan, April 14, 1977 ABSTRACT Picolinic acid reversibly inhibits the growth under 95% air/5% CO2, humidified atmosphere, at 37°. The of cultured cells. Fourteen other pyridine derivatives were in- cell lines used are listed in Table 1. Unless otherwise indicated, effective or toxic. Untransformed normal rat kidney (NRK) cells cells were planted at 1.5 X 105 cells per dish. Twenty-four hours are reversibly arrested in the G1 stage of the growth cycle as later, media were replaced by new media with or shown by cell counts, mitotic index, [3H]thymidine incorpora- (treated) tion, and flow microfluorometry. Flow microfluorometry was without (control) picolinic acid. All cells lines were treated with used to monitor the effects of picolinic acid on numerous other picolinic acid at 1.5,2,2.5,3, and 4 mM and analyzed for 4 days cell lines. Normal cells are blocked in GI, whereas transformed with media change every other day. cells show responses that are dependent upon the transforming Cells were analyzed for DNA content by flow microfluo- virus and independent of species or origin of the cell line. Kir- rometry (FMF) after trypsinization and suspension in pro- sten sarcoma virus-transformed cells are blocked in GI.
    [Show full text]
  • Chemical Products
    CUSTOM MANUFACTURING AND FINE CHEMICAL SOURCING 768 N. Bethlehem Pike ⚫ Lower Gwynedd, PA 19002 USA Tel: (215) 628-2946 ⚫ Fax: (215) 628-4262 ⚫ Web: www.richmanchemical.com Chemical Products This is a representative list of products which Richman Chemical Inc. supplied, sourced for our customers, or custom manufactured. This partial list shows only what we have done in the past, and it may not include what we are capable of doing for you. Therefore, if you are looking for a specific material not on our list, please call with your inquiry. Satisfying your unique or special needs is our full time business.
    [Show full text]
  • Novel 3,6-Dihydroxypicolinic Acid Decarboxylase Mediated Picolinic Acid
    bioRxiv preprint doi: https://doi.org/10.1101/457895; this version posted October 31, 2018. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 1 Novel 3,6-Dihydroxypicolinic Acid Decarboxylase Mediated Picolinic Acid 2 Catabolism in Alcaligenes faecalis JQ135 3 4 Jiguo Qiu1, Yanting Zhang1, Shigang Yao1, Hao Ren2, Meng Qian3, Qing Hong1, 5 Zhenmei Lu2*, and Jian He1,3 * 6 7 1 Key Laboratory of Agricultural Environmental Microbiology, Ministry of Agriculture, College of 8 Life Sciences, Nanjing Agricultural University, Nanjing, 210095, China 9 2 College of Life Sciences, Zhejiang University, Hangzhou, 310058, China 10 3 Laboratory Centre of Life Science, College of Life Sciences, Nanjing Agricultural University, 11 Nanjing, 210095, China 12 13 Running Title: Novel 3,6-Dihydroxypicolinic Acid Decarboxylase 14 15 Keywords: Alcaligenes faecalis, picolinic acid, 3,6-dihydroxypicolinic acid, 16 degradation, decarboxylase, amidohydrolase_2 17 18 * Address correspondence to Jian He, [email protected], or Zhenmei Lu, 19 [email protected] 20 21 1 / 25 bioRxiv preprint doi: https://doi.org/10.1101/457895; this version posted October 31, 2018. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 22 ABSTRACT 23 Alcaligenes faecalis strain JQ135 utilizes picolinic acid (PA) as sole carbon and 24 nitrogen source for growth. In this study, we screened a 6-hydroxypicolinic acid 25 (6HPA) degradation-deficient mutant through random transposon mutagenesis. The 26 mutant hydroxylated 6HPA into an intermediate, identified as 3,6-dihydroxypicolinic 27 acid (3,6DHPA) with no further degradation.
    [Show full text]
  • The Solvent Effect on Composition and Dimensionality of Mercury(II) Complexes with Picolinic Acid
    molecules Article The Solvent Effect on Composition and Dimensionality of Mercury(II) Complexes with Picolinic Acid Željka Soldin 1,* , Boris-Marko Kukovec 2,* , Dubravka Matkovi´c-Calogovi´cˇ 1 and Zora Popovi´c 1 1 Division of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia; [email protected] (D.M.-C.);ˇ [email protected] (Z.P.) 2 Department of Physical Chemistry, Faculty of Chemistry and Technology, University of Split, Rudera¯ Boškovi´ca35, HR-21000 Split, Croatia * Correspondence: [email protected] (Ž.S.); [email protected] (B.-M.K.) Abstract: Three new mercury(II) coordination compounds, {[HgCl(pic)]}n (1), [HgCl(pic)(picH)] (2), and [HgBr(pic)(picH)] (3) (picH = pyridine-2-carboxylic acid, picolinic acid) were prepared by reactions of the corresponding mercury(II) halides and picolinic acid in an aqueous (1) or alcohol– methanol or ethanol (2 and 3) solutions. Two different types of coordination compounds were obtained depending on the solvent used. The crystal structures were determined by the single- crystal X-ray structural analysis. Compound 1 is a one-dimensional (1-D) coordination polymer with mercury(II) ions bridged by chelating and bridging N,O,O0-picolinate ions. Each mercury(II) ion is four-coordinated with a bidentate picolinate ion, a carboxylate O atom from the symmetry-related picolinate ion and with a chloride ion; the resulting coordination environment can be described as a highly distorted tetrahedron. Compounds 2 and 3 are isostructural mononuclear coordination Citation: Soldin, Ž.; Kukovec, B.-M.; compounds, each mercury(II) ion being coordinated with the respective halide ion, N,O-bidentate Matkovi´c-Calogovi´c,D.;ˇ Popovi´c,Z.
    [Show full text]
  • Table 4: Protective Action Criteria (PAC) Rev. 29 Based on Applicable
    Table 4: Protective Action Criteria (PAC) Rev. 29a based on applicable 60-minute AEGLs, ERPGs, or TEELs. The chemicals are 3 listed in alphabetical order and the values are presented in mg/m . June 2018 Table 4 is an alphabetical list of the chemical substances and their corresponding PAC values in mass per unit volume (mg/m3). The conversion of ppm to mg/m3 was carried out assuming normal temperature and pressure, 25°C and 760 mm Hg. The columns presented in Table 4 provide the following information: Heading Definition No. The ordered numbering of the chemicals as they appear in this alphabetical listing Chemical Name The name of the chemical substance submitted to the PAC development team CASRN The Chemical Abstracts Service Registry Number1 for this chemical PAC-1 Based on the applicable AEGL-1, ERPG-1, or TEEL-1 value PAC-2 Based on the applicable AEGL-2, ERPG-2, or TEEL-2 value PAC-3 Based on the applicable AEGL-3, ERPG-3, or TEEL-3 value Chemicals for which AEGLs are available have their chemical name, CASRN, and AEGL values displayed in a bolded and larger font. Chemicals for which ERPGs are available, but not AEGLs, have their chemical name, CASRN, and ERPG values displayed in a bolded font. Chemicals for which TEELs are available, but no AEGLs or ERPGs, have their chemical name, CASRN, and values displayed using a regular font. Additional information on PAC values and TEEL values and links to other sources of information is provided on the Subcommittee on Consequence Assessment and Protective Actions (SCAPA) webpage at http://orise.orau.gov/emi/scapa/default.htm.
    [Show full text]
  • Influence of Low Dose-Rate Radiation on Metabolism
    Influence of Low Dose-Rate Radiation on Metabolism Takashi SUGIHARA, Katsuyoshi FUJIKAWA, Satoshi TANAKA, Ignacia TANAKA, Jun-ichiro KOMURA Department of Radiobiology Abstract To elucidate the influence of low dose-rate (LDR) radiation on metabolism, we have started quantitative analysis of the amount of low molecular-weight metabolites (metabolome analysis) in the liver of B6C3F1 male and female mice irradiated at a LDR of 20 mGy/day for 300 days (total dose: 6,000 mGy). Here we report preliminary results obtained this year. We observed changes in the amount of the compounds involved in the TCA cycle, gluconeogenesis and glycolysis (for example, fumaric acid, malic acid, glyceraldehyde triphosphate and phosphoenolpyruvate) in both male and female irradiated mice. These results suggest that metabolome analysis can be a useful tool for analyzing the biological effects of LDR radiation. Non-irradiated Irradiated Non-irradiated Irradiated Fig.1. Score plot of principal component analysis of the metabolites in the liver of male and female mice irradiated or non-irradiated at 20 mGy/day for 300 days. n = 4. 0.15 Asn Type2 His Galactosamine Phe Glucosamine Ascorbate 2-glucoside Hexanoic acid Lys S-Methylglutathione Xanthosine Adenine Pro Gln 0.1 Cysteine glutathione disulfide Isobutyryl CoA_divalent Glycerol 3-phosphate Leu Ala Trimethylamine Tyr XC0126 Type1 Gly Isovaleric acid Guanidinosuccinic acid Type1 Daminozide Ile GDP-glucose Trp Heptanoic acid Octanoic acid Valeric acid Ala-Ala GDP-mannose 1-Methyladenosine Pyridoxamine 5'-phosphate
    [Show full text]
  • Ternary Complexes of Cd(II) Involving Pyridine-2-Carboxylic Acid and Biorelevant Ligands
    41 Egypt. J. Chem. 59, No. 5, pp. 673- 686 (2016) Ternary Complexes of Cd(II) Involving Pyridine-2-carboxylic Acid and Biorelevant Ligands Eman M. Shoukry, Nagda G. Hosny, Mona F. Amin and Eman F. Mohamed Department of Chemistry, Faculty of Science (Girls), Al Azhar University, Nasr City,Cairo, Egypt. OMPLEX formation reactions involving Cd(II), pyridine -2- C carboxylic acid ( picolinic acid, PA) and various biorelevant ligands (L) containing different functional groups are investigated at 25 ºC and I = 0.10 M (NaNO3). The ligands (L) used are amino acids, peptides and DNA constituents. The results showed the formation of Cd(II)-(PA)-(L) complexes with amino acids and DNA constituents, peptides form both Cd(II)-(PA)-(L) complexes and the corresponding deprotonated amide species Cd(II)-(PA)- (LH-1). The relative stabilities of ternary complexes are compared with those of the corresponding binary complexes in terms of ∆ log K values. The concentration distribution of the complexes in solution was evaluated. Keywords: Cd(II), Picolinic acid, Amino acids, Peptides, DNA constituents, Stability constant. The great majority of the work of biological chemists is concerned with the coordination chemistry of essential metal ions in living organisms, and the examination of aspects of the interactions of these essential metal ions with the rest of the enzymes of the cells in which they are found. The present study, however, is concerned with the manipulation of the coordination environment of toxic metal ions in order to accelerate their excretion from the organism. The toxic effects of cadmium (II) are well documented (1) .
    [Show full text]
  • Table of Contents
    MONTANA TECH i CHEMICAL HYGIENE PLAN TABLE OF CONTENTS TABLE OF CONTENTS .......................................................................................... i STATEMENT OF POLICY .................................................................................... 1 CHEMICAL HYGIENE RESPONSIBILITIES ........................................................ 2 LABORATORY FACILITIES ................................................................................. 4 Maintenance ..................................................................................................... 4 Evaluation ......................................................................................................... 5 CONTROL MEASURES ....................................................................................... 5 Work Habits ...................................................................................................... 5 Laboratory Hygiene ........................................................................................... 6 Engineering Controls ........................................................................................ 6 Instrument Equipment and Use ........................................................................ 7 Personal Protective Equipment (PPE) .............................................................. 8 Eye Protection ............................................................................................. 8 Hand Protection ..........................................................................................
    [Show full text]
  • Asian Journal of Chemistry Asian Journal of Chemistry
    Asian Journal of Chemistry; Vol. 26, No. 8 (2014), 2395-2399 ASIAN JOURNAL OF CHEMISTRY http://dx.doi.org/10.14233/ajchem.2014.16023 Determination of Stability Constants of Mixed Ligand Complexes of Picolinic Acid and Other Bioactive Ligands with Zn(II) by Potentiometric Titration Method 1 1,2,* 1 NADA M. ARISHY , REDA A. AMMAR and ABDULRHMAN AL-WARTHAN 1Department of Chemistry, College of Science, King Saud University, P.O. Box 22452, Riyadh 11495, Saudi Arabia 2Department of Chemistry, College of Science, Al Azhar University, Cairo, Egypt *Corresponding author: E-mail: [email protected] Received: 9 July 2013; Accepted: 5 November 2013; Published online: 15 April 2014; AJC-15033 The stability constants of ternary complexes of Zn(II) with picolinic acid as primary ligand and some of bioactive ligands (e.g., amino acids and peptides) as secondary ligand were determined pH-metrically at 25 °C and ionic strength 0.1 mol/L NaNO3 in water solution. The possible formation of ternary complexes via simultaneous mechanisms has been confirmed by comparison with constructed theoretical curves. The stability of each ternary complexes was also investigated and compared with those of the corresponding binary complexes in terms of the ∆ log K parameter. In addition, the concentration distribution of the complexes formed in solution was evaluated. Keywords: Picolinic acid, Mixed ligand complexes, ∆∆∆ log K, Stability constants, Potentiometric studies. INTRODUCTION (amino acid and peptide) with Zn(II) were determined using potentiometric titration in water solution at 25 °C and an ionic Picolinic acid (P) is, chemically, pyridine-2-carboxalic strength (I) of 0.1 mol/L (NaNO ).
    [Show full text]
  • United States Patent (19) 11 Patent Number: 5,776,856 Narayanan 45) Date of Patent: Jul
    USOO.5776856A United States Patent (19) 11 Patent Number: 5,776,856 Narayanan 45) Date of Patent: Jul. 7, 1998 54 SOLUBLE POLYMER BASED MATRIX FOR 5,629.261 5/1997 Narayanan et al. .................... 5046 CHEMICALLY ACTWE WATER INSOLUBLE COMPONENTS Primary Examiner S. Mark Clardy 75 Inventor: Kolazi S. Narayanan, Wayne, N.J. Attorney, Agent, or Firm-Marilyn J. Maue; William J. Davis; Walter Katz (73) Assignee: ISP Investments Inc., Wilmington, Del. 57 ABSTRACT 21 Appl. No.: 795,022 This invention relates to a water soluble matrix composition comprising an anionic surfactant, a C to C alkyl 22 Filed: Feb. 4, 1997 pyrrollidone, urea and a water insoluble copolymer of vinyl (51) Int. Cl. ............................. A01N 25/30; CO5G 5/00; pyrrollidone with not more than 50 wt.% of a comonomer CO8L 33/OO selected from the group of an o-olefin, vinyl acetate, an 52 U.S. Cl. .......................... 504/116424/407; 514/950 acrylic or methacrylic acid ester and methacrylamide as a 7/904; 71/DIG. 1 free flowing particulate solid which matrix is suitably mixed 58) Field of Search ............................. s04/116424/407 with a water insoluble, chemically active component, such 514/950, 7/904, DG. 1 as an agrochemical, to provide a clear sprayable film form s ing emulsion, such as a non-leachable film on a plant or 56 References Cited other substrate surface. The invention also relates to the method of preparing the matrix and to the incorporation of U.S. PATENT DOCUMENTS an agrochemical concentrate and plant spray composition. 5,580,578 12/1996 Oshlack et al.
    [Show full text]