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Chromatographic Analysis of Low Molecular Weight Polar Compounds in Complex Environmental Matrices and Renewable Materials Jana Rousova

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Chromatographic Analysis of Low Molecular Weight Polar Compounds in Complex Environmental Matrices and Renewable Materials Jana Rousova University of North Dakota UND Scholarly Commons Theses and Dissertations Theses, Dissertations, and Senior Projects January 2017 Chromatographic Analysis Of Low Molecular Weight Polar Compounds In Complex Environmental Matrices And Renewable Materials Jana Rousova Follow this and additional works at: https://commons.und.edu/theses Recommended Citation Rousova, Jana, "Chromatographic Analysis Of Low Molecular Weight Polar Compounds In Complex Environmental Matrices And Renewable Materials" (2017). Theses and Dissertations. 2329. https://commons.und.edu/theses/2329 This Dissertation is brought to you for free and open access by the Theses, Dissertations, and Senior Projects at UND Scholarly Commons. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of UND Scholarly Commons. For more information, please contact [email protected]. CHROMATOGRAPHIC ANALYSIS OF LOW MOLECULAR WEIGHT POLAR COMPOUNDS IN COMPLEX ENVIRONMENTAL MATRICES AND RENEWABLE MATERIALS by Jana Rousová Bachelor of Science, University of Chemical Technology, 2008 Master of Science, University of Chemical Technology, 2011 A Dissertation Submitted to the Graduate Faculty of the University of North Dakota in partial fulfillment of the requirements for the degree of Doctor of Philosophy Grand Forks, North Dakota August 2017 Copyright 2017 Jana Rousová ii PERMISSION Title Chromatographic Analysis of Low Molecular Weight Polar Compounds in Complex Environmental Matrices and Renewable Materials. Department Chemistry Degree Doctor of Philosophy In presenting this dissertation in partial fulfillment of the requirement for a graduate degree from the University of North Dakota, I agree that the library of this University shall make it freely available for inspection. I further agree that permission for extensive copying for scholarly purposes may be granted by the professor who supervised my dissertation work or, in her absence, by the chairperson of the department or the dean of the graduate school. It is understood that any copying or publication or other use of this dissertation or part thereof for financial gain shall not be allowed without my written permission. It is also understood that due recognition shall be given to me and the University of North Dakota in any scholarly use which may be made of any material in my dissertation. Jana Rousová 07/21/2017 iv TABLE OF CONTENT LIST OF TABLES ..................................................................................................................... ix LIST OF FIGURES ...................................................................................................................xii LIST OF ABBREVIATIONS ...................................................................................................... xvi ACKNOWLEDGMENTS ........................................................................................................ xviii ABSTRACT ......................................................................................................................... xviii I. CHAPTER CHALLENGES IN ANALYSIS OF LOW MOLECULAR WEIGHT POLAR COMPOUNDS & STATEMENT OF PURPOSE ........................................................................................ 1 II. CHAPTER DETERMINATION OF IMPURITIES IN BIOPRODUCED SUCCINIC ACID ............ 6 II.1. BACKGROUND ................................................................................................. 6 II.2. MATERIALS AND METHODS .............................................................................. 8 II.2.1 Studied samples ................................................................................................. 8 II.2.2 Chemicals ........................................................................................................... 9 II.2.3 Sample preparation ......................................................................................... 10 II.2.4 Instrumentation ............................................................................................... 12 II.2.5 Data processing ................................................................................................ 12 II.3. RESULTS AND DISCUSSION ............................................................................. 14 II.3.1 Extraction vs direct analysis ............................................................................. 14 II.3.2 Initial identification of impurities .................................................................... 15 II.3.3 Development of quantification method for analysis of acids and saccharides as the most abundant impurities .............................................................................................. 17 II.3.4 Limits of detection and repeatability ............................................................... 22 II.3.5 Characterization of succinic acid samples ....................................................... 22 v II.3.5.1 Abundance of acids, saccharides, and polyalcohols ........................................................... 23 II.3.5.2 Final Bacterial Process Samples .......................................................................................... 25 II.4 CONCLUSIONS................................................................................................. 25 III. CHAPTER CHARACTERIZATION OF BIOLOGICALLY ACTIVE MOLECULES IN PULICARIA JAUBERTII EXTRACTS USING GAS AND LIQUID CHROMATOGRAPHY AND MASS SPECTROMETRY ....................................................................................................... 27 III.1. BACKGROUND .............................................................................................. 27 III.2. MATERIALS AND METHODS ........................................................................... 28 III.2.1 Plant collection ................................................................................................ 28 III.2.2 Chemicals ........................................................................................................ 28 III.2.3 Preparation of the PJ extract and its fractionation......................................... 28 III.2.4 Chemical characterization of PJ fractions. ...................................................... 29 III.3. RESULTS AND DISCUSSION ............................................................................ 31 III.3.1 Determination of bioactive fractions .............................................................. 31 III.3.2 Chemical characterization of PJ fractions ....................................................... 31 III.4 CONCLUSIONS................................................................................................ 38 IV. CHAPTER DETERMINATION OF TRANS-RESVERATROL AND ITS METABOLITES IN RAT SERUM USING LIQUID CHROMATOGRAPHY WITH HIGH-RESOLUTION TIME OF FLIGHT MASS SPECTROMETRY .............................................................................................. 39 IV.1. BACKGROUND .............................................................................................. 39 IV.2. MATERIALS AND METHODS .......................................................................... 41 IV.2.1 Materials ......................................................................................................... 41 IV.2.2 Synthesis and purification of RES analogs and deuterated RSs ..................... 42 IV.2.3 Sample preparation ........................................................................................ 43 IV.2.4 Instrumentation .............................................................................................. 44 IV.2.5 ESI optimization .............................................................................................. 44 IV.2.6 LC-ESI-HRMS conditions for serum analysis ................................................... 47 vi IV.2.7 Data processing .............................................................................................. 47 IV.3. RESULTS AND DISCUSSION ............................................................................ 48 IV.3.1 Evaluation of ESI conditions ........................................................................... 48 IV.3.2 Calibration parameters and limits of detection ............................................. 50 IV.3.3 Concentration of RES and its metabolites in rat serum and their impact on tumor growth ........................................................................................................................ 52 IV.4. CONCLUSIONS .............................................................................................. 57 V. CHAPTER METHOD DEVELOPMENT FOR DETERMINATION OF TRACE CONCENTRATIONS OF ALDEHYDES AND CARBOXYLIC ACIDS IN PARTICULATE MATTER ........................... 58 V.1. BACKGROUND ............................................................................................... 58 V.2. MATERIALS AND METHODS ........................................................................... 66 V.2.1 Materials .......................................................................................................... 66 V.2.2 Sample preparation ......................................................................................... 67 V.2.2.1 Evaluation of derivatization conditions .............................................................................. 67 V.2.2.2 Extraction and derivation of PM samples ........................................................................... 69 V.2.3 Instrumentation
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