The design of fluorous chemistry for a middle school classroom, for carbohydrate microarrays, and for the automated solution-phase synthesis of bacterial oligosaccharides from Group A Streptococcus and Staphylococcus aureus

Abstract

Introduction 12 Brief summary of the procedure and its place in the middle school curriculum 15 Constant relevance to real world applications 18 Teacher and student perspectives of the hydrophobicity/fluorophilicity unit 19 Conclusion 23 Hazards 23 CHAPTER 3. Probing the Limitations of Fluorous Content for Tag-Mediated Microarray Formation Abstract Introduction Results and discussion Conclusion Experimental section CHAPTER 4. Automated Solution-Phase Synthesis of the Cell Wall Oligosaccharides of Group A Streptococcus Abstract Introduction iii Results and discussion Conclusion Experimental section CHAPTER 5. Automated Solution-Phase Synthesis of the Cell Wall Oligosaccharides of Staphylococcus aureus Abstract Introduction Results and discussion Conclusion Experimental Section CHAPTER 6. Conclusions and Future Directions ACKNOWLEDGMENTS APPENDIX A. CHAPTER 2 WORKSHEETS 99 APPENDIX B. CHAPTER 3 1 H AND 13 C NMR SPECTRA APPENDIX C. CHAPTER 4 1 H AND 13 C NMR SPECTRA BIBLIOGRAPHY CHAPTER 1 GENERAL INTRODUCTION Dissertation Organization This dissertation is comprised of six different chapters. Chapter 1 is a review of the basic concepts and principles that are involved with chapters 2 thru 5. Chapter 2 reports a hydrophobicity/fluorophilicity unit introduced into the middle school classroom. Chapter 3 discusses the synthetic route of a di-fluorous tag. Comparative studies of the di-fluorous tag versus the mono-fluorous tags were carried out by microarray experiments. Chapter 4 demonstrates the automated solution-phase synthesizer in the synthesis of Group A Streptococcus (GAS) branched oligosaccharide. In chapter 5, Staphylococcus aureus monosaccharides were developed in order to be synthesized by the automated solution-phase synthesizer. This chapter will discuss the difficulties in building the S. aureus monomers and the methodology of the certain protecting groups. Finally, chapter 6 will conclude the dissertation with a summary of the projects and the future directions of each project.