Labeled mimics of N-Acetyl-D-Fucosamine

Abstract

The synthesis of N-acetyl-D-fucosamine and derivatives will be attempted from inexpensive commercially available starting materials. The final products contain medicinally important markers such as fluorine, which can be viewed easily by examining 19F nuclear magnetic resonance spectra. Protective group chemistry will have a major role in this work and enables the selective introduction of markers into N-acetyl-D-fucosamine derivatives. Another crucial chemical process includes inverting the stereochemistry at C-4 of the precursor, namely N-acetyl-D-glucosamine. 1-D and 2-D nuclear magnetic resonance studies will be used to verify regiochemical and stereochemical outcomes of reactions. Carbohydrates such as N-acetyl-D-fucosamine and its derivatives mimic the types of molecules found in the capsular polysaccharides of bacteria such as Staphylococcus aureus. If incorporated into the bacterium's capsular polysaccharides, this should modify the capsular polysaccharides possibly allowing the human immune system to recognize the bacterium. Therefore, these types of compounds are likely candidates for antibiotics against such bacteria.