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

摘要

This dissertation demonstrates the innovative methods and applications of fluorous chemistry. Fluorous chemistry will first be introduced into the classroom setting at the middle school level. The advantages of fluorous chemistry correlating with surface chemistry becomes a great tool of helping students understand more about the science at a molecular level. Next, fluorous chemistry has advanced the way carbohydrate microarrays and small molecule microarrays have help with binding studies. The covalent binding of most microarrays leaves the molecules on the microarray slide rigid, but with the non-covalent binding of the fluorous-fluorous interactions allow the molecule to be more flexible and bind easier to the binding partner. Here we synthesized three different fluorous linkers (C8F17-mono, C6F13-mono, and Di-C6F13 linkers) and studied the non-covalent interactions of each linker. We did this by using known binding studies of mannose to concovalin A. Finally, it has been found that fluorous chemistry has helped with the purification process as a linker due to the fluorous biphasic component. Here we use fluorous solution-phase extraction to help with the purification of oligosaccharides in the automated solution-phase synthesizer. In the end a fluorous linker was used to help create the oligosaccharides of Group A Streptococcus and Staphylococcus aureus. Fluorous chemistry can be used for many different applications and modernize old techniques.