The Synthesis of Substituted 3-Amido-Piperdinols to Study Transition State Mechanism of Protease Inhibition

Bryn Mawr Chemistry

Professor Malachowski

Graduate Student Tina M. Ross

Peptidoaldehydes (1) have been well recognized as effective transition state analogue inhibitors of peptidases, esterases, and metalloproteases. Hemiaminals (3), which have the same oxidation state as aldehydes, might also serve as protease inhibitors, while allowing extended-binding interactions in the enzyme active site. In this poster presentation, we document the preliminary synthesis of hemiaminals (3). The synthetic strategies to make 3 and the current progress on the synthesis will be discussed.