Synthesis of an Unnatural Amino Acid via Oxynitrilase and Stereospecific Palladium Catalyzed Reactions.
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The importance of chiral molecules has recently been manifested in the pronounced shift of pharmaceutical companies from racemic to enantiopure drugs.In 2000, pharmaceutical companies grossed over 100 billion dollars for sales of chiral medicines.Additionally, asymmetric drugs now account fro one-third of all pharmaceutical sales worldwide. Unfortunately however, single enantiomer pharmaceuticals are extremely difficult to produce because enantiomers exhibit identical physical properties making separation extremely challenging. Our research this summer demonstrates how functional and versatile enantiopure molecules can be synthesized via the enzyme oxynitrilase. Oxynitrilase, an enzyme in almond meal, has the ability to create enantiopure cyanohydrins from achiral aldehydes. A second key part of our synthesis process is further able to maintain stereo and regiochemistry via a palladium catalyzed azide reaction. Using these two main reactions, and others, our research attempts to synthesize an amino acid that has the opposite stereochemistry of its natural counterpart. Furthermore, we hope to produce versatile single enantiomer molecules that can sere as medicinal building blocks.