The synthesis of N-acetyl-D-fucosamine and N-((2R,3R,4R)-2,4-dihydroxy-6-methylene-5-oxo-tetrahydro-2H-pyran-3-yl)acetamide will be pursued from the
inexpensive starting material N-acetyl-D-glucosamine. These carbohydrates are mimics
of intermediates used by Staphylococcus aureus in the construction of its protective
capsular polysaccharide, which allows the bacteria to evade both the host immune system
and antibiotics in current use. Synthesis of these molecules allows for carbohydrate
mimics to be developed which can be used as targeted antibiotics needed for use against
antibiotic-resistant Staphylococcus aureus strains.
Characterization by nuclear magnetic resonance spectroscopy will allow
determination of structural conformation, of structures' dependence on solvent while in
solution, and presence of the desired product. These studies will be carried out to be
compared with other structural determination techniques in wide use today. Knowledge
of the solution state structure of a molecule is necessary to understand the possible
interactions in biological systems which must be understood in pharmaceutical
development. Recent developments in NMR techniques allow for multi-dimensional
spectra which can relate interconnected atoms in a molecule to provide information on
the relative spatial orientation of atoms within a molecule.