DOCSLIB.ORG

Structural Analysis of Carbohydrates by Mass Spectrometry Chiharu Konda Purdue University

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Structural Analysis of Carbohydrates by Mass Spectrometry Chiharu Konda Purdue University Purdue University Purdue e-Pubs Open Access Dissertations Theses and Dissertations Fall 2013 Structural Analysis of Carbohydrates by Mass Spectrometry Chiharu Konda Purdue University Follow this and additional works at: https://docs.lib.purdue.edu/open_access_dissertations Part of the Analytical Chemistry Commons Recommended Citation Konda, Chiharu, "Structural Analysis of Carbohydrates by Mass Spectrometry" (2013). Open Access Dissertations. 141. https://docs.lib.purdue.edu/open_access_dissertations/141 This document has been made available through Purdue e-Pubs, a service of the Purdue University Libraries. Please contact [email protected] for additional information. Graduate School ETD Form 9 (Revised 12/07) PURDUE UNIVERSITY GRADUATE SCHOOL Thesis/Dissertation Acceptance This is to certify that the thesis/dissertation prepared By Chiharu Konda Entitled Structural Analysis of Carbohydrates by Mass Spectrometry Doctor of Philosophy For the degree of Is approved by the final examining committee: Yu Xia Chair Peter T. Kissinger Nikolai R. Skrynnikov Hilkka I. Kenttamaa To the best of my knowledge and as understood by the student in the Research Integrity and Copyright Disclaimer (Graduate School Form 20), this thesis/dissertation adheres to the provisions of Purdue University’s “Policy on Integrity in Research” and the use of copyrighted material. Approved by Major Professor(s): ____________________________________Yu Xia ____________________________________ Approved by: Robert E. Wild 10/25/2013 Head of the Graduate Program Date i STRUCTURAL ANALYSIS OF CARBOHYDRATES BY MASS SPECTROMETRY A Dissertation Submitted to the Faculty of Purdue University by Chiharu Konda In Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy December 2013 Purdue University West Lafayette, Indiana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¶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lPDD'U0DU\:LUWKDQG'U$QG\7DR , DSSUHFLDWH \RXUNLQGQHVVHVIRURIIHULQJPHDQDFFHVVWR \RXUHTXLSPHQWVLQVWUXPHQWV DQGDOVRKHOSIURPVWXGHQWVLQ\RXUJURXS ,ZRXOGOLNHWRWKDQN'U-LP+DJHU)UDQN/RQGU\DQG'U/DUU\&DPSEHOOIURP $%6FLH[IRUDYDULHW\RIKHOSVVXFKDVLQVWDOOLQJWKHVFDQGHVLJQHUPRGLILFDWLRQRQRXU LQVWUXPHQWDQGJLYLQJVXJJHVWLRQVWRLPSURYHP\SDSHU 7R DOO RI P\ FXUUHQW ODE PDWHV WKDQN \RX IRU RIIHULQJ VXFK D QLFH DQG KRPH\ DWPRVSKHUH , WUXO\ HQMR\HG RXU PXOWLFXOWXUDO HQYLURQPHQW &KDVLW\ /RYH ZH DUH 3URIHVVRU;LD¶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l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m/z,RQV*HQHUDWHGIURP/LQNHG'LVDFFKDULGHV 7KH(IIHFWRI&,'&RQGLWLRQVRQWKH)RUPDWLRQRIm/z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
Load more

Recommended publications
  • Structure of an Acidic Polysaccharide Elaborated by Acetobacter Sp
    Agric. Biol. Chem., 50 (5), 1271 ~1278, 1986 1271 Structure of an Acidic Polysaccharide Elaborated by Acetobacter sp. NBI 10051" Kenji Tayama, Hiroyuki Minakami, Seiichi Fujiyama, Hiroshi Masai and Akira Misaki* NakanoBiochemical Research Institute, NakanoVinegar Co., Ltd., Handa, Aichi 475, Japan * Faculty of Science of Living, Osaka City University, Sugimoto-cho, Sumiyoshi, Osaka 558, Japan Received November 19, 1985 An extracellular acidic polysaccharide elaborated by Acetobacter sp. NBI1005 was composed of D-glucose, D-galactose, D-mannose, and D-glucuronic acid (approximate molar ratio, 6 : 2 : 1 : 1). Methylation and fragmentation analysis by partial acid hydrolysis indicated that the polysaccharide has a branched structure containing a backbone chain of /?-(l ->4)-linked D-glucose residues, two out of every four glucose residues being substituted at the 0-3 positions to form two kinds of branches, one consisting of D-mannose and D-glucuronic acid residues and the other of (l ->6)-linked D-galactose and D-glucose residues. Some microorganisms belonging to Ace- cosyl-(l ->4)-D-glucuronosyl-(l ->2)-D-man- tobacter species have been knownto produce nose.9) This paper reports the structural fea- extracellular polysaccharides, such as cellu- ture of polysaccharide AM-1, as revealed by lose,1* dextran,2) levan,3) and an acidic poly- methylation, fragmentation analysis, and en- saccharide,4* and also soluble, /?-(l-»2)- zymatic degradation. branched, £-(1 ^4)-D-glucan5) and )8-(l -»2)- D-glucan.6) In the course of study on acetic MATERIALS AND METHODS acid bacteria (genera Acetobacter and Glu- conobacter) having a high productivity of Materials. Polysaccharide AM-1of Acetobacter sp.
    [Show full text]
  • Improving the Utilization of Isomaltose and Panose by Lager Yeast Saccharomyces Pastorianus
    fermentation Article Improving the Utilization of Isomaltose and Panose by Lager Yeast Saccharomyces pastorianus Javier Porcayo Loza 1,2,† , Anna Chailyan 3, Jochen Forster 3 , Michael Katz 3, Uffe Hasbro Mortensen 2,* and Rosa Garcia Sanchez 3,* 1 Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, 2800 Kongens Lyngby, Denmark; [email protected] 2 Department of Bioengineering, Technical University of Denmark, 2800 Kongens Lyngby, Denmark 3 Carlsberg A/S, Carlsberg Research Laboratory, 1799 Copenhagen V, Denmark; [email protected] (A.C.); [email protected] (J.F.); [email protected] (M.K.) * Correspondence: [email protected] (U.H.M.); [email protected] (R.G.S.) † Current address: Graphenea S.A., 20009 San Sebastian, Spain. Abstract: Approximately 25% of all carbohydrates in industrial worts are poorly, if at all, fermented by brewing yeast. This includes dextrins, β-glucans, arabinose, xylose, disaccharides such as isomaltose, nigerose, kojibiose, and trisaccharides such as panose and isopanose. As the efficient utilization of carbohydrates during the wort’s fermentation impacts the alcohol yield and the organoleptic traits of the product, developing brewing strains with enhanced abilities to ferment subsets of these sugars is highly desirable. In this study, we developed Saccharomyces pastorianus laboratory yeast strains with a superior capacity to grow on isomaltose and panose. First, we designed a plasmid toolbox for Citation: Porcayo Loza, J.; Chailyan, the stable integration of genes into lager strains. Next, we used the toolbox to elevate the levels of A.; Forster, J.; Katz, M.; Mortensen, the α-glucoside transporter Agt1 and the major isomaltase Ima1.
    [Show full text]
  • Polyphenolic Compounds Extracted and Purified from Buddleja Globosa
    molecules Article Polyphenolic Compounds Extracted and Purified from Buddleja Globosa Hope (Buddlejaceae) Leaves Using Natural Deep Eutectic Solvents and Centrifugal Partition Chromatography Jeniffer Torres-Vega 1 , Sergio Gómez-Alonso 2 , José Pérez-Navarro 2 , Julio Alarcón-Enos 3 and Edgar Pastene-Navarrete 1,3,* 1 Laboratorio de Farmacognosia, Departamento de Farmacia, Facultad de Farmacia, Universidad de Concepción, Concepción PC4030000, Chile; [email protected] 2 Regional Institute for Applied Scientific Research, Faculty of Chemical Sciences, University of Castilla-La Mancha, PC13071 Castilla-La Mancha, Spain; [email protected] (S.G.-A.); [email protected] (J.P.-N.) 3 Laboratorio de Síntesis y Biotransformación de Productos Naturales, Universidad del Bío-Bío, Chillán PC3800708, Chile; [email protected] * Correspondence: [email protected]; Tel.: +56-(42)-246-3000 Abstract: Chemical profiling of Buddleja globosa was performed by high-performance liquid chro- matography coupled to electrospray ionization (HPLC-DAD-ESI-IT/MS) and quadrupole time-of-flight high-resolution mass spectrometry (HPLC-ESI-QTOF/MS). The identification of 17 main phenolic com- pounds in B. globosa leaf extracts was achieved. Along with caffeoyl glucoside isomers, caffeoylshikimic Citation: Torres-Vega, J.; acid and several verbascoside derivatives (β-hydroxyverbascoside and β-hydroxyisoverbascoside) were Gómez-Alonso, S.; Pérez-Navarro, J.; Alarcón-Enos, J.; Pastene-Navarrete, identified. Among flavonoid compounds, the presence of 6-hydroxyluteolin-7-O-glucoside, quercetin-3- E. Polyphenolic Compounds O-glucoside, luteolin 7-O-glucoside, apigenin 7-O-glucoside was confirmed. Campneoside I, forsytho- Extracted and Purified from Buddleja side B, lipedoside A and forsythoside A were identified along with verbascoside, isoverbascoside, Globosa Hope (Buddlejaceae) Leaves eukovoside and martynoside.
    [Show full text]
  • Enzymatic Synthesis of Α-Glucosides Using Various Enzymes
    Chapter 1 Reviews: Enzymatic Synthesis of α-Glucosides Using Various Enzymes 1.1 Introduction In recent years, transglycosylation or reverse hydrolysis reactions catalyzed by glycosidases have been applied to in vitro synthesis of oligosaccharides1-8) and alkylglycosides7-14). Glucosylation is considered to be one of the important methods for the structural modification of compounds having -OH groups with useful biological activities since it increases water solubility and improves pharmacological properties of the original compounds. Enzymatic synthesis is superior to the chemical synthesis methods in such cases that the enzymatic reactions proceed regioselectively and stereoselectively without protection and deprotection processes. In addition, the enzymatic reactions occur usually under mild conditions: at ordinary temperature and pressure, and a pH value around neutrality. Various compounds, such as drugs13, 17), vitamins and their analogues15, 16), and phenolic compounds17), have been anomer-selectively glucosylated by microbial glycosidases. In this chapter, the methods for enzymatic synthesis of several glucosides and mechanism of xanthan gum synthesis by Xanthomonas campestris are reviewed in details. 1 1.2 Enzymatic synthesis of glucosides 1.2.1 Neohesperidin α-glucoside synthesis using cyclodextrin glucanotransferase of Bacillus sp. A2-5a18) Citrus fruits contain two groups of flavonoid glycosides that have either rutinose (L-rhaminopyranosyl-α-1, 6-glucopyranoside) or neohesperidose (L- rhaminopyranosyl-α-1, 2-glucopyranoside) as their saccharide components. Hesperidin from mandarin oranges is tasteless. Neohesperidin from grapefruits is intensely bitter and important in citrus juices since it is converted into sweet dihydrochalcone derivatives by hydrogenation. However, since their solubilities in water are very low, enzymatic modification of neohesperidin was expected for applications in the food industry.
    [Show full text]
  • Electron Ionization
    Chapter 6 Chapter 6 Electron Ionization I. Introduction ......................................................................................................317 II. Ionization Process............................................................................................317 III. Strategy for Data Interpretation......................................................................321 1. Assumptions 2. The Ionization Process IV. Types of Fragmentation Pathways.................................................................328 1. Sigma-Bond Cleavage 2. Homolytic or Radical-Site-Driven Cleavage 3. Heterolytic or Charge-Site-Driven Cleavage 4. Rearrangements A. Hydrogen-Shift Rearrangements B. Hydride-Shift Rearrangements V. Representative Fragmentations (Spectra) of Classes of Compounds.......... 344 1. Hydrocarbons A. Saturated Hydrocarbons 1) Straight-Chain Hydrocarbons 2) Branched Hydrocarbons 3) Cyclic Hydrocarbons B. Unsaturated C. Aromatic 2. Alkyl Halides 3. Oxygen-Containing Compounds A. Aliphatic Alcohols B. Aliphatic Ethers C. Aromatic Alcohols D. Cyclic Ethers E. Ketones and Aldehydes F. Aliphatic Acids and Esters G. Aromatic Acids and Esters 4. Nitrogen-Containing Compounds A. Aliphatic Amines B. Aromatic Compounds Containing Atoms of Nitrogen C. Heterocyclic Nitrogen-Containing Compounds D. Nitro Compounds E. Concluding Remarks on the Mass Spectra of Nitrogen-Containing Compounds 5. Multiple Heteroatoms or Heteroatoms and a Double Bond 6. Trimethylsilyl Derivative 7. Determining the Location of Double Bonds VI. Library
    [Show full text]
  • Rational Design of an Improved Transglucosylase for Production of the Rare Sugar Nigerose† Cite This: Chem
    ChemComm COMMUNICATION Rational design of an improved transglucosylase for production of the rare sugar nigerose† Cite this: Chem. Commun., 2019, 55,4531 Jorick Franceus,a Shari Dhaene,a Hannes Decadt,a Judith Vandepitte,a Received 25th February 2019, Jurgen Caroen,b Johan Van der Eycken,b Koen Beerensa and Tom Desmet *a Accepted 26th March 2019 DOI: 10.1039/c9cc01587f rsc.li/chemcomm The sucrose phosphorylase from Bifidobacterium adolescentis (BaSP) can be used as a transglucosylase for the production of rare sugars. We designed variants of BaSP for the efficient synthesis of nigerose from sucrose and glucose, thereby adding to the inventory of rare sugars that can conveniently be produced from bulk sugars. Rare sugars hold tremendous potential for practical applications in various industries.1 Regardless, few of them have been exploited Fig. 1 Transglucosylation of glucose by mutant Q345F of the B. adoles- centis sucrose phosphorylase, resulting in the synthesis of maltose and commercially due to their scarcity in nature which prevents nigerose. them from being isolated in large quantities. These compounds have consequently become attractive targets for biocatalytic production processes starting from affordable and widely avail- kojibiose, but instead produces an equimolar mixture of maltose able carbohydrates.2 and nigerose (Fig. 1).9–12 The sucrose phosphorylase from Bifidobacterium adolescentis Nigerose is the rare a-(1,3)-bonded disaccharide of glucose that (BaSP; carbohydrate-active enzyme database family GH13) is a occurs in nature as a constituent of polysaccharides such as nigeran. particularly interesting candidate enzyme for the production of It is also found in Japanese rice wine or sake, hence its alternative such rare sugars.
    [Show full text]
  • C's Name Formula Bp (ºC) Structure 1 Methane CH4 -162 H-(CH2)
    Chem 350 Jasperse Ch. 3 Handouts 1 ALKANE NAMES (Memorize) (Sections 3.2) # C’s Name Formula Bp (ºC) Structure 1 Methane CH4 -162 H-(CH2)-H 2 Ethane C2H6 -89 H-(CH2)2-H 3 Propane C3H8 -42 H-(CH2)3-H 4 Butane C4H10 0 H-(CH2)4-H 5 Pentane C5H12 36 H-(CH2)5-H 6 Hexane C6H14 69 H-(CH2)6-H 7 Heptane C7H16 98 H-(CH2)7-H 8 Octane C8H18 126 H-(CH2)8-H 9 Nonane C9H20 151 H-(CH2)9-H 10 Octane C10H22 174 H-(CH2)10-H Industrial Alkanes (Sections 3.5) Name # C’s Boiling Range Use Natural Gas C1-C3 Gas Fuel (70% methane) “Petroleum Gas” C2-C4 <30º Heating, Gas Propane C3 -42º Propane tanks, camping, etc. Gasoline C4-C9 30-180º Car fuel Kerosene C8-C16 160-230º Jet fuel Diesel C10-C18 200-320º Truck fuel Heavy Oils C16-C30 300-450º Motor Oils High temp Paraffin Vacuum Asphalt Never Distills Coke Never Distills Chem 350 Jasperse Ch. 3 Handouts 2 Nomenclature of Alkanes (Sections 3.3) Systematic IUPAC Rules for Branched and Substituted Alkanes (Section 3.3B) 1. Longest continuous C-chain “core name” 2. Number core chain from an end nearest a substituent 3. Name substituents as “alkyl” groups: 4. Specify the location of substituents using numbers (hyphenate the #’s) • If >2 substituents, list alphabetically • Use di-, tri-, tetra- if the same substituent is repeated. (But ignore these in alphabetizing). Punctuation Notes: • Hyphenate numbers • Do not put a space between substituents and the core name Special Names for Some 3 or 4-carbon Substituents H3C CH3 CH Memorize H3C C H3C CH3 Isopropyl t-butyl or tert-butyl H2 H2 CH3 H3C C H3C C CH H3C CH Others C C C C CH3 H3C C H2 H H H2 2 2 H2 n-propyl n-butyl isobutyl s-butyl (n for "normal") Another Classification System Primary (1º): with one attached carbon Secondary (2º): with two attached carbons Tertiary (3º): with three attached carbons H C C C C C C C C H 1º H 2º C 3º Very Complex Substituents (Not responsible) Substituent: (1-ethyl-2,3-dimethylpentyl) Overall: 9-(1-ethyl-2,3-dimethylpentyl)nonadecane Chem 350 Jasperse Ch.
    [Show full text]
  • Structural Features
    1 Structural features As defined by the International Union of Pure and Applied Chemistry gly- cans are structures of multiple monosaccharides linked through glycosidic bonds. The terms sugar and saccharide are synonyms, depending on your preference for Arabic (“sukkar”) or Greek (“sakkēaron”). Saccharide is the root for monosaccha- rides (a single carbohydrate unit), oligosaccharides (3 to 20 units) and polysac- charides (large polymers of more than 20 units). Carbohydrates follow the basic formula (CH2O)N>2. Glycolaldehyde (CH2O)2 would be the simplest member of the family if molecules of two C-atoms were not excluded from the biochemical repertoire. Glycolaldehyde has been found in space in cosmic dust surrounding star-forming regions of the Milky Way galaxy. Glycolaldehyde is a precursor of several organic molecules. For example, reaction of glycolaldehyde with propenal, another interstellar molecule, yields ribose, a carbohydrate that is also the backbone of nucleic acids. Figure 1 – The Rho Ophiuchi star-forming region is shown in infrared light as captured by NASA’s Wide-field Infrared Explorer. Glycolaldehyde was identified in the gas surrounding the star-forming region IRAS 16293-2422, which is is the red object in the centre of the marked square. This star-forming region is 26’000 light-years away from Earth. Glycolaldehyde can react with propenal to form ribose. Image source: www.eso.org/public/images/eso1234a/ Beginning the count at three carbon atoms, glyceraldehyde and dihydroxy- acetone share the common chemical formula (CH2O)3 and represent the smallest carbohydrates. As their names imply, glyceraldehyde has an aldehyde group (at C1) and dihydoxyacetone a carbonyl group (at C2).
    [Show full text]
  • Influence of Conjugation Axis on the Optical and Electronic Properties Of
    Article pubs.acs.org/joc Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles † ‡ ‡ † † Brian C. Tlach, Aimeé L. Tomlinson, Alden G. Ryno, Dawn D. Knoble, Dana L. Drochner, † Kyle J. Krager, and Malika Jeffries-EL*, † Department of Chemistry, Iowa State University, Ames, Iowa 50010, United States ‡ Department of Chemistry, University of North Georgia, Dahlonega, Georgia 30597, United States *S Supporting Information ABSTRACT: Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d′]bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated. Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually. ■ INTRODUCTION Among the aforementioned examples, the benzo[1,2-d:4,5- d′]bis(oxazole) (BBO)-based cruciforms are particularly During the past four decades, interest in the development of π- interesting, since these molecules have two different con- conjugated materials has increased due to their potential use as jugation pathways: 2,6-conjugation through the oxazole rings replacements for inorganic materials in a variety of semi- and 4,8-conjugation through the central benzene ring (Scheme conducting applications including field effect transistors − − 1).
    [Show full text]
  • Physical Sciences Content
    Foreword In order to improve learning outcomes the Department of Basic Education conducted research to determine the specific areas that learners struggle with in Grade 12 examinations. The research included a trend analysis by subject experts of learner performance over a period of five years as well as learner examination scripts in order to diagnose deficiencies or misconceptions in particular content areas. In addition, expert teachers were interviewed to determine the best practicesto ensure mastery of thetopic by learners and improve outcomes in terms of quality and quantity. The results of the research formed the foundation and guiding principles for the development of the booklets. In each identified subject, key content areas were identified for the development of material that will significantly improve learner's conceptual understanding whilst leading to improved performance in the subject. The booklets are developed as part of a series of booklets, with each bookletfocussing onlyon one specific challenging topic. The selected content is explained in detail and include relevant concepts from Grades 10 - 12 to ensure conceptual understanding. The main purpose of these booklets is to assist learners to master the content starting from a basic conceptual level of understanding to the more advanced level. The content in each booklets is presented in an easy to understand manner including the use of mind maps, summaries and exercises to support understanding and conceptual progression. These booklets should ideally be used as part of a focussed revision or enrichment program by learners after the topics have been taught in class. The booklets encourage learners to take ownership of their own learning and focus on developing and mastery critical content and skills such as reading and higher order thinking skills.
    [Show full text]
  • Heuristics for Searching Chemical Structures a Thesis Presented To
    Heuristics for Searching Chemical Structures A Thesis presented to the Faculty of the Graduate School University of Missouri-Columbia In Partial Fulfillment of the Requirements for the Degree Master of Science by Nandini Basu Dr. Toni Kazic, Thesis Supervisor May 2007 The undersigned, appointed by the Dean of the Graduate School, have examined the thesis entitled HEURISTICS FOR SEARCHING CHEMICAL STRUCTURES presented by Nandini Basu A candidate for the degree of Master of Science And hereby certify that in their opinion it is worthy of acceptance. Dr. Toni Kazic Dr. Chi-Ren Shyu Dr. Mary Schaeffer ACKNOWLEDGMENTS I am deeply indebted to my research advisor Dr. Toni Kazic for giving me an opportunity to resume my research in and complete my Computer Science MS program. Without her guidance, support and encouragement this would not have been possible. I would like to thank Dr. Mary Polaco and Dr. Shyu for serving in my committee and helping me in my thesis. I would like to thank the Klotho team for helping me with structures. And also the other team members Amith, Archana, Avanthi, Bill, Deepthi, Gaurav, Raman, Jiahui, Fatten, Meeta and Michael. My friends made a difficult journey lot of fun and much easier, especially Cathy, Charu, Deepak, Karan, Karthik, Paco, Nikunj, Raj, Shiva, Shraddha, Sundeep and Vibha. All my relatives gave me constant encouragement and I would like to take this opportunity to thank them. And above all, I would like to thank my father Prabhat Kumar Basu, my mother Minoti Basu, my brother Pradipta Kumar Basu and my sister-in-law Sarmistha Basu.
    [Show full text]
  • Kalinka Christopher Thesis.Pdf (3.535Mb)
    UNIVERSITY OF WISCONSIN-LA CROSSE Graduate Studies DOES THE YICJI OPERON CONTRIBUTE TO UROPATHOGENIC ESCHERICHIA COLI FITNESS WHEN CULTURED IN HUMAN URINE A Manuscript Style Thesis Submitted in Partial Fulfillment of the Requirements for the Degree of Master of Science in Microbiology Christopher Kalinka College of Science and Health Microbiology May, 2020 ABSTRACT Kalinka, C.P. Does the yicJI operon contribute to uropathogenic Escherichia coli fitness when cultured in human urine. MS in Microbiology, May 2020, 81pp. (W.Schwan). Escherichia coli is a common bacterium found in the intestinal tracts of many mammals. A medically relevant type of E. coli is known as uropathogenic E. coli (UPEC). One of the most critical research areas involves genes that are responsible for bacterial fitness, like the yicJ gene, which encodes the sodium:galactoside symporter; yicI, which encodes the α-glycosidase YicI; and frzR, which encodes FrzR that is the activator of the frz operon and a putative activator of the yicJI operon. To examine what impacts yicJ, yicI, the yicJI operon, and frzR had on fitness, each gene was cloned into the pMMB91 plasmid and growth curves in urine and buffered Luria broth were done for each recombinant strain in 96-well plates from 0 h-72 h. The growth curve studies demonstrated that overexpression of yicJI and frzR significantly enhanced growth in shaken human urine, whereas overexpression of yicJI attenuated growth in Luria-Bertani broth. Additionally, a portion of the promoter region of frzR was also cloned into the pCRISPathBrick plasmid to act as a gRNA scaffold for dCas9 to knock down the gene expression of the frzR gene.
    [Show full text]