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Design and Synthesis of Analogs of <I>Myo</I>-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies

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Design and Synthesis of Analogs of <I>Myo</I>-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies University of Tennessee, Knoxville TRACE: Tennessee Research and Creative Exchange Doctoral Dissertations Graduate School 12-2017 Design and Synthesis of Analogs of myo-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies Tanei J. Ricks University of Tennessee, Knoxville, [email protected] Follow this and additional works at: https://trace.tennessee.edu/utk_graddiss Part of the Biochemistry Commons, Biology Commons, Medicinal-Pharmaceutical Chemistry Commons, Microbiology Commons, Molecular, Cellular, and Tissue Engineering Commons, and the Organic Chemistry Commons Recommended Citation Ricks, Tanei J., "Design and Synthesis of Analogs of myo-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies. " PhD diss., University of Tennessee, 2017. https://trace.tennessee.edu/utk_graddiss/4780 This Dissertation is brought to you for free and open access by the Graduate School at TRACE: Tennessee Research and Creative Exchange. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of TRACE: Tennessee Research and Creative Exchange. For more information, please contact [email protected]. To the Graduate Council: I am submitting herewith a dissertation written by Tanei J. Ricks entitled "Design and Synthesis of Analogs of myo-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies." I have examined the final electronic copy of this dissertation for form and content and recommend that it be accepted in partial fulfillment of the equirr ements for the degree of Doctor of Philosophy, with a major in Chemistry. Michael D. Best, Major Professor We have read this dissertation and recommend its acceptance: Brian K. Long, David C. Baker, Todd B. Reynolds Accepted for the Council: Dixie L. Thompson Vice Provost and Dean of the Graduate School (Original signatures are on file with official studentecor r ds.) Design and Synthesis of Analogs of myo-Inositol, Serine, and Cysteine to Enable Chemical Biology Studies A Dissertation Presented for the Doctor of Philosophy Degree The University of Tennessee, Knoxville Tanei J. Ricks December 2017 DEDICATION This dissertation is dedicated to the loving memory of Toyian Renauld Williams (November 7, 1980-June 28, 2014) ii ACKNOWLEDGEMENTS First and foremost, I would like to thank Ms. Terry Kennedy. She was the first person that made me realize how much I loved chemistry. I would not be here without her guidance and enthusiasm for teaching. Next I would like to thank my parents, Joe Ricks and Elizabeth Ricks. I struggled mightily trying to find my way through adolescence. I did not always make the best decisions, but my parents helped me find my way. Next I would like to thank my grandparents, Joe and Annette Ricks as well as Gloria Simms. They’ve always been my biggest cheerleaders and my biggest critics. Their struggles in life helped me understand what it meant to achieve success. Thank you to Almeca Simms. I did not understand or fully appreciate the sacrifice you made at a young age, but I am thankful that you ultimately decided to make it. Next I would like to thank Jermaine Mack for all of the free haircuts and a place to dwell when I was trying to figure things out. Thank you to Delvon Mack for always being one of my most supportive cousins. The wisdom and knowledge you dropped on me at such a young age until now has been a huge help. Special thanks to Barbara and Harold Williams. You treated many of us just like you treated your own children growing up and those memories are a vital part of who I am. Thank you to all of the cousins and others I grew up with as well. My friends have been my chosen family and some of my greatest supporters on this journey. Thanks to Carlton Knight for being my A1 since day 1. I moved to a totally new place in high school and he was the friendliest face iii there. I cannot imagine what life would’ve been like without this friendship in high school. The same goes for Stanley Flanders. The three of us got into a lot of trouble together and I would not trade that experience for anything. The Trio rides again. Thank you Derick Kerr. I met you through Carlton and I feel like that was destiny as well. You’ve been just as much of a pivotal part of my adult life as the other 2. We are truly brothers from different mothers. Thank you to Jonathan Morris. You’ve always been a dependable person in my life Jmo and I greatly appreciate it. I have also met some truly amazing people since I moved to Knoxville to complete this PhD. I would first like to thank Sam and Erin Rosolina. Sam was my rock in the chemistry department. I could always depend on a righteous point of view from him. He became one of my biggest allies and I’m proud to call him a friend and chemistry peer. Erin shares the same righteous spirit as Sam and she has been a huge ally. I thank you both for your constant love and support even though we don’t agree about the Arby’s sign. I promise we won’t watch anymore taser videos. The same goes for Tyler and Casey Anthony, Josh Schmeling and Tina Le-Phan, and Eddie and Kendhl Seabright. Our makeshift family has enriched my life in so many ways. I am forever grateful for that. My Team Hard Knox brothers are some of the purest spirits I’ve met since moving here. Matthew Norton is one of the most important connections I’ve made in Knoxville. So much came from a random Facebook message about MTG and I’m glad I put myself out there. Long live Perro Rabioso. Mario Lillard has been a iv mentor and a leader to our team. He’s also been a great friend and support. It is time for us to get back on the road fellas. We have a pro tour dominate. Thank you to Nolan Mitchell. This has been a very unlikely, but very welcomed friendship. You’ve grown into someone I can depend on for mostly anything and that’s been extremely helpful. I can only hope I’ve reciprocated the same for you. My professional career has been full of people that have contributed to my overall success. Huge thanks to Dr. Thomas Crute. He was the one that helped me stick with chemistry in undergrad and I’m sure I wouldn’t be here without his guidance today. Also, thanks to Dr. Joseph Hauger for selecting me for the SRSP scholarship. That support gave me the extra push I needed to focus on my studies full time. Dr. Donna Hobbs prepared me for graduate school with her no nonsense approach to teaching. She has been a huge blessing to my scientific career. Dr. Chris Bates was pivotal to me developing my biology skills. He prepared me to be a well-rounded chemical biologist. Big thanks to all of the wonderful people in the Augusta State University (it will always be that to me) chemistry and physics department. My time at UTK has been an extremely transformative experience and I am a better person because of it. Thank you to Dr. Sekeenia Haynes for being a valuable mentor and professional contact. Whether it’s just letting me blow off steam or advising me on what me next steps should be as a graduate student, you’ve been an invaluable resource and an excellent mentor. Thank you to all of the wonderful PEER staff, current and past including Dr. Gladys Alexandre and v Donna Ford. Thank you to all of my collaborators including Dr. Francisco Barerra, Dr. Daiane Santana Alves, and Justin Westerfield. Special thanks to Chelsi Cassilly for being an exemplary partner in research. I’ve enjoyed working with you these past 3 years and wish you much success in your future endeavors. Thanks as well to Dr. Todd Reynolds for the endless guidance, willingness to help design experiments, and open his lab to me. Thank you to Dr. Brian Long and Dr. David Baker for serving on my committee. Your advice over the years has helped me become the chemist I am today and I am thankful for that. Part of my UTK career took an unexpected turn that got me into podcasting. I want to send a special thank you to Christopher Hines for giving me the opportunity to be a part of the Greatness Podcast Network. It’s been a pleasure working with you and I’m anxious to see where this goes. Also thank you to others who have given me an opportunity to be a guest on their platforms including Andrew Morton at the Intelligent Rebel Squadcast and D. Rook of the Project Rook Podcast. I want to thank the current and past members of the Best lab, especially Shahrina Alam. I had so much fun working with you Shahrina and you were a huge inspiration to me. I can only hope I get to work with someone like you again. Thank you to my research advisor Dr. Michael Best for giving me the opportunity to work in your lab. I cannot think of a time where I didn’t feel comfortable coming to you for advice about anything whether it was work related or personal. I always wondered whether or not I made the right choice in advisor vi when I came here, but looking back over the past 5 years, I’m sure I did. You’re the epitome of everything an advisor should be, part mentor, part counselor, part friend. My last acknowledgement is for Eunice Hong.
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