Preparing Substrates for Cyclopropanted Fatty Acid sythnase in order to pursuit biocatalytic cyclopropanation

The project is an effort to prepare cyclopropanated derivatives of long-chain cis alkenes, using an enzyme called cyclopropane fatty acid synthase (CFA synthase). This enzyme is naturally occurring in some bacteria, where it performs the cyclopropanation reaction on cis-alkene fatty acid chains of cell membranes. The enzyme has been sequenced and its mechanism of action studied previously in the literature. However, it has never been employed biocatalytically for organic synthesis. Cyclopropanated long alkyl chains are a relatively under-investigated class of chemical compounds, since the cyclopropanation is difficult to achieve by chemical synthesis. In conjunction with a collaborator at Virginia Tech, we are investigating  the use of CFA synthase for preparing cyclopropanated fatty acid methyl esters, starting from cis-alkene fatty acid methyl esters.