KMichael-01
Synthesis of a carbohydrate derivative
Health, Human Disease & Diagnostics
Preferred major field of study or minimum required skills
The student should be a chemistry or biochemistry major and have some basic knowledge of general and organic chemistry, such as the concept of molarity; acid-base chemistry; sp, sp2, and sp3 hybridization of orbitals; intermolecular forces; the polarity of compounds; some functional groups; stereochemistry; some basic chemical reactions, e.g. oxidation, reduction, nucleophilic substitution; and some basic laboratory skills such as distillation, and extraction.
Scholarly significance/intellectual merit
This summer project entails performing organic reactions on the carbohydrate galactose in a multiple-step synthesis, i.e. esterification, silylation, and acetalization of particular hydroxyl groups. The student will also learn how to work up organic reactions, and how to purify and characterize the desired products. The final product of this multiple-step synthesis is an important building block for the synthesis of more complex saccharides that exist on the cell surface of certain Leishmania parasites that cause the disease leishmaniasis. Since leishmaniasis patients have an immune response to these saccharides, having these saccharides in hand opens doors for the development of diagnostic tools and even a vaccine for leishmaniasis.
Research question(s)
The objective of this summer research experience is to synthesize a fully protected carbohydrate building block. Can this compound be accessed by an alternative, more efficient synthesis when compared to an established procedure?
Methods/techniques/instruments to be learned/utilized
The student will gain hands-on experience in synthetic organic chemistry: (a) performing reactions under inert gas atmosphere and anhydrous conditions; (b) monitoring reactions by thin layer chromatography (TLC); (c) purifying products by column chromatography; (d) characterizing compounds by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy.