Researcher(s)
- Kelly Sprenkel, Chemistry, Millersville University
- Colette Makara, Chemistry, University of Delaware
Faculty Mentor(s)
- Joseph Fox, Chemistry and Biochemistry, University of Delaware
Abstract
Biorthogonal reactions are a class of non-natural chemical transformations that can proceed efficiently without interfering with biological functional groups. Trans-cyclooctenes are prominent in biorthogonal chemistry due to their reaction kinetics with tetrazines. Since the introduction of tetrazine ligation with trans-cyclooctenes in 2008, the synthesis of trans-cyclooctenes has been a major area of interest. Due to their application in the fields of chemical biology, nuclear medicine, and material science, there has been a major drive to improve the throughput of the synthesis of trans-cyclooctenes derivatives. This work describes the photochemical isomerization of trans-cyclooctenes from cis-cyclooctenes, using a high throughput photochemical flow method employing a custom reactor for the large-scale synthesis trans-cyclooctenes derivatives. Keto-trans-cyclooctenes can be transformed to amines via reductive animation. This work also describes the use of various solvents to transform keto-trans-cyclooctenes to imines, and use of various reducing agents to transform those imines to amines. Various conditions were tested to test the efficiency and speed of the solvents and reducing agents tested. The ability to produce these amines faster and more efficiently will improve the accessibility of these compounds.