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DESIGN and SYNTHESIS of CHELATING COMPOUNDS and SOLID-SUPPORTED CHELATORS for METAL DEPLETED SOLUTIONS Surendra Dawadi University of Missouri-St

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DESIGN and SYNTHESIS of CHELATING COMPOUNDS and SOLID-SUPPORTED CHELATORS for METAL DEPLETED SOLUTIONS Surendra Dawadi University of Missouri-St University of Missouri, St. Louis IRL @ UMSL Dissertations UMSL Graduate Works 7-25-2014 DESIGN AND SYNTHESIS OF CHELATING COMPOUNDS AND SOLID-SUPPORTED CHELATORS FOR METAL DEPLETED SOLUTIONS Surendra Dawadi University of Missouri-St. Louis, [email protected] Follow this and additional works at: https://irl.umsl.edu/dissertation Part of the Chemistry Commons Recommended Citation Dawadi, Surendra, "DESIGN AND SYNTHESIS OF CHELATING COMPOUNDS AND SOLID-SUPPORTED CHELATORS FOR METAL DEPLETED SOLUTIONS" (2014). Dissertations. 230. https://irl.umsl.edu/dissertation/230 This Dissertation is brought to you for free and open access by the UMSL Graduate Works at IRL @ UMSL. It has been accepted for inclusion in Dissertations by an authorized administrator of IRL @ UMSL. For more information, please contact [email protected]. DESIGN AND SYNTHESIS OF CHELATING COMPOUNDS AND SOLID-SUPPORTED CHELATORS FOR METAL DEPLETED SOLUTIONS By SURENDRA DAWADI Master of Science (Chemistry), 2010 A DISSERTATION Submitted to the Graduate School of the UNIVERSITY OF MISSOURI - ST. LOUIS In partial Fulfillment of the Requirements for the Degree of DOCTOR OF PHILOSOPHY in CHEMISTRY August, 2013 Dissertation Committee Prof. Christopher D. Spilling, Ph.D. (Advisor) Prof. Wesley R. Harris, Ph.D. Prof. Alexei V. Demchenko, Ph.D. Prof. James J. O’Brien, Ph.D. Dawadi, Surendra, 2013, UMSL, p.ii ACKNOWLEDGEMENTS Foremost, I would like to express my profound gratitude to my mentor Professor Christopher D. Spilling for his guidance, encouragement, enthusiastic support, and useful critiques during these past five years. He has always been motivating, encouraging, and enlightening. Dr. Spilling’s humor and friendly sarcasm allowed me to laugh, lightening my perspective when I became too serious. He continually delivered not only a motivation towards research but also an excitement in teaching. His impression will always be a part of my professional life. Without his guidance and persistent help, this dissertation would not have been possible. I sincerely thank Professor Wesley R. Harris for his help in this research project and also for being in my dissertation committee. I would like to thank him for teaching me analytical techniques required for the completion of the project and answering my numerous questions. I would like to express my sincere gratitude to other dissertation committee members Prof. Alexei Demchenko and Prof. James O’Brien for their time and effort. I would also like to thank Dr. Bruce Hamper, Prof. Valerian D’Souza, and all my teachers for contributing to my graduate school and research experience and their encouragement. I would like to thank Department of Chemistry and Biochemistry at the University of Missouri-St. Louis (UMSL) for providing me a platform to gain teaching and research experience. It is my pleasure to thank my former and current labmates in the UMSL Spilling group: Dr. Raj Malla, Dr. Mahesh Paudyal, Dr. Sudeshna Roy, Benjamin Martin, Mercy Kiiru, and Jeremy Ridenour, who provided excellent support in the lab. Special thanks go to Jeremy and Ben for proofreading the whole thesis. I would like to thank Harris lab Dawadi, Surendra, 2013, UMSL, p.iii member Nicolas Bardol for his help during my intermittent presence in the Harris lab. I would also like to thank all my friends at UMSL and in St. Louis. Without them I could not have done my PhD while enjoying every moment of it. I would like to acknowledge Alkymos Inc., a startup company, and its principal investigator Robert A. Yokel (College of Pharmacy, University of Kentucky), and the National Institute of Health (NIH) for financial support. I would like to thank Dr. Spilling along with Dr. Harris and Dr. Yokel for bringing me into this extremely important project. My highest gratitude goes to my father, Ganesh Prasad Dawadi; brother, Ananda Dawadi; and sisters, Kamala and Sabitra, for their love, support, and understanding during the long years of my education. Finally, and most importantly, I would like to thank my wife Sarmila. Her support, encouragement, and steady love are undeniably the most important factors for this achievement. I would like to thank her for being able to take care of our five-year-old daughter Renesa and two-year-old son Rohan in my long absences. I would like to thank my daughter and son for making me laugh when I arrive home after a long day. Dawadi, Surendra, 2013, UMSL, p.iv LIST OF ABBREVIATIONS 3,4-HP ...........................................................................................3-hydroxy-4-pyridinones Å ............................................................................................................................Angstrom AAS....................................................................................Atomic absorption spectroscopy Ac................................................................................................................................Acetyl AHA...................................................................................................Acetohydroxamic acid APDMES..................................................................(3-aminopropyl)dimethylethoxysilane BAL.......................................................................................................British anti-Lewisite BH3.............................................................................................................................Borane Bn................................................................................................................................Benzyl Boc.........................................................................................................tert-butoxycarbonyl Ca(glu)2....................................................................................................Calcium gluconate Cbz.................................................................................................................Carboxybenzyl CERCLA.......Comprehensive Environmental Response, Compensation, and Liability Act CHCl3..................................................................................................................Chloroform CH2Cl2........................................................................................................Dichloromethane Cu(acac)2..........................................................................................Copper acetylacetonate d.................................................................................................................................Doublet DCC....................................................................................N,N'-Dicyclohexylcarbodiimide DCM ..................................................................Dichloromethane (or Methylene chloride) dd............................................................................................................Doublet of doublets DFO..........................................................................................................Desferioxamine-B Dawadi, Surendra, 2013, UMSL, p.v DIPEA...............................................................................................Diisopropylethylamine DMF..............................................................................................N,N-Dimethylformamide DMAP....................................................................................N,N-Dimethylamino pyridine DMPS................................................................................2.3-dimercaptopropane sulfonate DMSA.......................................................................................2,3-dimercaptosuccinic acid DMSO.....................................................................................................Dimethyl sulfoxide DNA...................................................................................................Deoxyribonucleic acid dr...........................................................................................................Diastereomeric ratio EDC .........................................................1-ethyl-3-(3-dimethylaminopropyl)carbodiimide EDTA.................................................................................Ethylenediamine tetraacetic acid Et...................................................................................................................................Ethyl EtOAc................................................................................................................Ethyl acetate Et2O...................................................................................................................Diethyl ether EtOH......................................................................................................................... Ethanol Et3N.................................................................................................................Triethylamine FAB.................................................................................................Fast atom bombardment FDA......................................................................................Food and Drug Administration h................................................................................................................................ Hour(s) HCl............................................................................................................hydrogen chloride HOBt..................................................................................................Hydroxybenzotriazole HPLC...................................................................High
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