Synthesis of Enantiopure CompoundsUsing the Enzyme Oxynitrilase.
Our method is a multi step process. We are coupling the use of the enzyme oxynitrilase with palladium. The focus of my research is the enzyme steps. The first step was to develop and efficient method to create cyanohydrins using the enzyme. Then a carbonate reaction is run on the cyanohydrin making it more fit for use with palladium. I have optimized both these reactions for the highest enantiomeric excess and the best yields. We have achieved greater than 99% enantiomeric excess on all three of the substrates we have worked with. The yields are also excellent, around 90% for the enzyme step, and around 80% for the carbonate step. The second part of my focus was to determine a way to make our enzyme more versatile. It will only take a very specific kind of aldehyde, and while this might not be changed we plan on altering the product of the enzyme reaction. To do this we used Grubb's catalyst which combines two terminal alkenes and gives of ethylene gas. This research is just in its early stages and there will be more to come.
Pace, Aaron, "Synthesis of Enantiopure CompoundsUsing the Enzyme Oxynitrilase." (2001). URC Student Scholarship.
NSF-Award for the Integration of Research and Education Fellowship